Being back in NYC after having dabbled in calling it my home between nine sublets over five years was heartwarming. There were a couple of places I wanted to visit, like Cava (for what my Gen Z colleagues call slop bowls) and Shu Jiao Fu Zhou (for cheap dumplings), but more than anything, I wanted to see my friends.

I wouldn’t say that I lack friends back home in Palo Alto, but being in NYC felt different. Day-to-day, i’s hard to keep in touch with friends who don’t live in the same city as you. Not because I don’t have the time, but because of the coordination friction, the distractions that are always within arm’s reach, and the perpetual occupation of the mind. I can’t remember the last time when I truly felt bored and thought to call up a random friend. Culturally, we’ve also stopped expecting calls from our friends, which is a complete 180 from calling our friends’ landlines as kids.

5 Non-AI moments this month

#1 - My friend Isaac celebrated his 30th birthday in Half Moon Bay with a group forage. That morning, I missed the fish n’ chips lunch because I was playing 5v5 basketball at the Stanford gym, but I got there just before the foraging began. I soaked up the warm sun as I walked to the beach in my t-shirt, shorts, and $2 garage sale flip flops. The extent of my preparation was having a single-day fishing license purchased, but other than that, I was winging it. As I walked and waded across the low-tide mix of rock, seaweed, and other ocean stuff, I started to feel the wind pick up. The hill above the beach had been blocking the wind, but not anymore. I was too stubborn to turn back and just got started. The six of us were locked in like truffle pigs, scouring for signs of purple sea urchin. At first, we struggled to find anything worth taking back, but it was like the four-minute mile. After the first uni was harvested, we knew it was possible, and started finding more. My feet were in the cold ocean water and the rest of my body was getting blasted by wind. My right hand wielded a random metal rod to scrape sea urchin and my left was for wiping snot off my face. After half an hour of tunnel-visioning on urchin, we shifted to mussels, which were in such abundance, they made up the ground that we stood on. The harvest was plentiful and I didn’t even get to enjoy it. But it’s all good. It was the activity itself that made it fun.

#2 - Right before I left for NYC, my founder asked me to visit his favorite tea shop in San Francisco to buy some gifts for our customers. I was already planning to visit an old coworker anyways for lunch so I said sure. As I biked to Song Tea & Ceramics with AirPods giving me turn-by-turn directions, it dawned on me how not-AI this was. I couldn’t help but notice I was on this very human side quest of gift-giving. I didn’t even use a manmade machine to get there - just my human-powered bike. AI is a powerful technology but it’s hard for me to envision doomsday scenarios of mass unemployment or AGI terrorism. Even for a company that builds AI agents, we’re still going to conferences every month and I guess in this case, biking to gift tea for our customers.

#3 - On my first night in New York, I went straight to a meetup for Free Agents, the community that I started. We’re all on different journeys, yet share a similar skepticism of the conventional career path. Some are looking for jobs again, while others are working on their own thing. We’re all scattered across the world and meet over Zoom, so getting together in-person was a delightful switch-up.

#4 - Somehow, with all the offerings of a city like NYC, I ended up watching a movie with my friend Joe. After feasting on fish stew, spicy fried chicken, and mapo tofu at Chili, we watched Project Hail Mary. About 20 minutes into the movie, I went to reach for the popcorn and the entire bucket spilled (not quietly) on the floor. Good thing it comes with free refills. Also - the movie itself was awesome, highly recommend.

#5- This past week, I hopped on a call to discuss a potential partnership. This was my first time meeting them, but I was given the context - we had met them at a recent conference in Las Vegas when the hosted a fancy steak dinner. There were two people from the other company on the call, but one guy did most of the talking. I pulled up his LinkedIn profile and saw that he had spent over 25 years in the industry, mostly in business development. At the start, there was more small talk than usual - catching up after Vegas, my colleague explaining that he had his video off since he was taking the train down to San Luis Obispo, and then that somehow turned into a conversation about surfing. The other guy asked if I also surf, which I confirmed. From that point on, the rest of the call was hella chill. We still have to see if it pans out, but the vibes were good. At the end, the other guy told my colleague that the next time he visits his neighborhood pizzeria, he’ll have a free pie waiting for him. Apparently he knows the owner. “Tell ‘em Buzzy sent ya.”

An observation on the current state of careers

Between catching up with friends in NYC and my own experience at work, I notice most people around me fall into one of three career modes:

#1 - Unemployed and looking for a job

They’re having a rough time. I can relate since it took me six months to find a job last year. Job searching is daunting and everyone I’ve talked to feels a bit desperate and anxious, despite the data indicating hiring is actually increasing across roles like PM, engineering, and recruiting. Something doesn’t add up, and I don’t think it’s directly due to AI replacing jobs, although that does seem to be the case for entry-level roles unfortunately.

AI has made it easier to apply to jobs, resulting in employers receiving a deluge of AI-written messages that lack any authenticity or care. As a result, it’s hard to sift through the slop for genuine applications. For example:

Another indirect effect of AI is that companies are tripping over themselves trying to keep up with the pace of change. I see it at my own company. We have open roles we’re trying to fill, but the relative importance of recruiting feels lower compared to pursuing new customers and building new features for existing ones.

There’s also a new bridge AI provides to help lessen the urgency of a new hire. Previously, if there was too much work, then you’d immediately think to hire a new person to take on the extra load. Now, you can first try to augment yourself with AI to be more productive. With tools like Claude Code and Cursor, an individual’s contributions are more elastic and can flex up simply by consuming more tokens. This only works up until a certain point. For example, my startup doesn’t have any marketing or sales people, so we’ve been using AI tools to design materials and personalize messages, but these one-off workflows don’t actually equate to a full-time marketer or salesperson.

Perhaps what I’m trying to say is that the matching process between job seeker and employer has become less efficient. The old way of sending in a resume is no longer effective (although I got my job by directly applying on LinkedIn). When the old way stops working, it doesn’t mean the world comes to a standstill - it just means it’s time to find a new way. For job seekers who aren’t new grads, my advice is to keep learning, be creative, demonstrate intentionality, and most importantly, have faith.

#2 - Unemployed and on sabbatical

I have a few friends who recently quit their jobs and are taking time to figure out what’s next. Given how dynamic things are, I’m glad I have the stability of a full-time job, but I can also see how now is a great time to be untethered. Nearly all knowledge is at our fingertips and an idea can be transformed into a product over a weekend. For those who have the financial resources and the conviction to bet on themselves, it’s never been a better time. Also, it doesn’t have to be about starting your own thing. It’s totally valid to pursue a career break to simply rest, travel, or spend more time with family. Ultimately, it boils down to making an intentional choice and fully accepting it and the associated tradeoffs.

#3 - Employed and overworked

I’m sure some people are coasting, putting in 20-30 hours a week, but it seems like most of my employed friends are grinding on an unsustainable path towards eventual burnout. I caught up with a friend working at a well-known AI startup and he shared his explanation for why work is currently all-consuming. The echo chamber of AI has perpetuated a sense of urgency among the entire industry. If you’re at an AI startup, you need to sprint a marathon every day or else your director competitors or the labs (OpenAI, Anthropic, Google DeepMind) will put you out of business. The message is clear: There’s a small window of opportunity. It’s now or never.

I’ve written about sustainable ambition before, and the idea continues to resonate with me. AI is a never-ending buffet of technology. It’s up to us to decide when we’re full.

Given I work at a startup and use AI tools to build AI products, I experience this slippery slope every day. We’ve become more efficient at work, but instead of working less, each individual worker is now producing more more and taking on new tasks that previously wouldn’t have been done. It’s required me to practice self-awareness of how I feel throughout the day and discernment around what tasks are actually going to move the needle.

There’s an economic concept that explains why this keeps happening. Jevons’ paradox suggests that as a machine or tool becomes more cost-efficient, consumption increases. You’d think that if a machine needs fewer resources for the same output, then total consumption would decrease, but actually the opposite occurs. When steam engines became more efficient with coal, overall coal consumption rose. When cities add an extra lane to a highway, there’s induced demand, meaning more people start driving on that highway. When applied to how we work, it means that we’re inclined to fill the newly freed-up time that AI enables with just more work.

AI changes how we work, but it doesn’t relieve us of the responsibility to choose what work means in the context of our overall lives, and what we’re willing to sacrifice at its expense.

The pull of total work has never been stronger. But we don’t win this battle by pushing back. We flow through the resistance through presence, wisdom, and the daily embodied practice of remembering who we are beyond our work.

P.S. I still coach! It’s honestly been a nice break of not mentioning anything coaching-related, but I still love this work and have continued to coach part-time alongside my full-time job. Check out my coaching website to learn more and reach out!

I spent half of February away from home, starting in Jackon Hole and arriving back in Palo Alto on February 15th. On Valentine’s Day, my girlfriend and I drove eight hours from Salt Lake City to Reno. Per the occasion, I booked a slightly nicer hotel than my usual modus operandi (an Airbnb chosen from the far left of the pricing bar graph). Upon arrival, there was a Shrek-themed rave on the premises that shook the entire lobby with the familiar booming bass of my early 20s. Thankfully once we were in our room, it was quiet and actually quite posh.

This month, my attention teeter-tottered. At more times than I’d like to admit, I would boot up Instagram desktop to click a few stories and then log out after noticing how much content wasn’t from people I consented to consume from. But in what I would deem progress, I unlinked my Readwise account from Substack. Posts now go straight to my inbox, a useful forcing function to prune my subscriptions for what can truly go head-to-head with physical books.

Here’s what’s to come below:

• A poem - the first I’ve written since it was required in school

• A short story about diapers

• Feynman’s 12 Problems

• What I read this month

• Intentions for March

Ripples

A tiny droplet questions its role
will it ever be
as powerful as the big tsunami wave?
What can a mere speck do
beyond being the pitter patter of rainfall?
From one leaf to another,
the droplet rolls
in quiet isolation
Until the day it lands in a lake
and loses its boundary
A body of water, millions of droplets, at once
Lines blur
in the sea of cohesion
Who is you and who is I?
A flat pebble skips across the surface,
dimpling it before sinking
Ripples emerge, ring after ring
each one an echo of the last
The tiny droplet at the center,
with radii of love emanating outwards
The far flung reach began with it
and ends at the edge of nowhere
Which is to say
Everywhere
The droplet stopped asking to be a wave
And remembered it was the ocean all along

Diapers

All week I had been refreshing OpenSnow’s forecast multiple times a day, eager to see how big the storm would get. I drove back home to my mom’s anyway. In order to rent out the house, we needed to clear out everything.

I faced a mountain of adult diapers, most in boxes, some thrown into garbage bags, but all clean, all unopened.

My grandma and grandpa don’t need them anymore. At least not these ones. They’re still alive but we recently moved them to LA, where it’s more affordable to find caregivers.

My grandparents have been in the slow process of dying over the last few years. I used to see them strolling around the neighborhood when I would get off the school bus. Close enough to make sure I was safe, far enough that I couldn’t complain too much. Now, getting them outside at all is a whole event.

As I took down picture frames off the wall, I noticed the impeccable posture of my grandma in the photos. Her spine upright with eyes smiling straight into the camera. I’d almost forgotten she’d looked like that.

I became aware of the fact that I was dropping off hundreds of adult diapers as I handed box after box to the Goodwill employee. Would he think they were meant for me? I brushed it off. I’ve been to thrift stores before, and never once seen adult diapers for sale. So I unloaded the boxes as quickly as I could, before they could ask any questions, and then bolted. Only to return a couple hours later with another carload. And then later, another one.

The time pressure added to the intensity of this moving out. Mom had a flight to catch, and I had my friends’ baby shower to attend.

On the third and final trip to Goodwill, cradling armfuls of clothes, electronics, office supplies, a rug, and of course, more adult diapers, I couldn’t help but wonder if I should’ve just brought them to the baby shower. I’ve heard young parents complain all the time about the cost of diapers. Plus it was reassuring that they’d certainly be used, versus potentially being bought off a Goodwill shelf. It was too late, I had already donated them all.

At the baby shower, there was a diaper changing relay race where competitors took turns changing diapers on stuffed animals roughly the same size as a human baby. Then I realized I made the right call in not gifting them. The diapers aren’t the same size.

Feynman’s 12 Problems

Physicist Richard Feynman once said:

“You have to keep a dozen of your favorite problems constantly present in your mind, although by and large they will lay in a dormant state. Every time you hear or read a new trick or a new result, test it against each of your twelve problems to see whether it helps. Every once in a while there will be a hit, and people will say, “How did he do it? He must be a genius!”

Three years ago, I made a first attempt on what I deem my 12 favorite problems. But looking at them now, I know I can do better. The first six were personal challenges that I was navigating on my sabbatical, all boiling down to wanting more certainty; a fool’s errand. The next six weren’t much better - all too vague and not authentic enough.

I haven’t completed it yet, but here are some updates to what I think are problems worth my attention:

• Attention: The battle is twofold: protecting what we have from eroding to modern addictions that siphon our attention, while rebuilding the ability to focus on a single activity for extended periods of time. When I was at my ski lease in Tahoe, another guest was diligently working on a puzzle. People that do puzzles earn my admiration. There are so many distractions out there that the ability to not only choose to start a puzzle, but also to finish one seems herculean to me. In a few years, when AI has seeped into all the crevices of the economy, it’s the puzzle-doers that I’ll turn to for wisdom.

• Loneliness: Sadly, there are millions of people today who walk past each other feeling isolated and longing for someone to connect with. In my experience, it’s the mirage that we concoct internally that somehow, we are the only ones suffering or ashamed or guilty that keeps us from asking for help or showing up in our communities.

• AI: If it helps you do a job, use AI. If it’s like going to the gym, don’t use it. I’m excited about how AI can shape how we work, but I’m concerned about what it means for all the metaphorical gyms. When AI is used to replace the thing we’re doing for the sake of doing it, it becomes like having a robot bench press for you, mistakenly thinking you’ll still reap the gains. The problem becomes how to resist the temptation to apply AI to everything. Discerning between what is like a job vs. what is like the gym across all of life’s activities becomes an essential meta-skill.

• Climate change: I haven’t been plugged into the climate scene (my last newsletter was published in 2024), but it’s back on my mind, in part due to the lack of snow this year. When I see the literal billions of dollars going into AI, the second order effects are straightforward to play out: more energy and not enough of the renewable kind to supply it. To be honest, I feel a bit stuck here. Policy change seems to be the strongest lever. The biggest opportunities in climate tech are hardware or in the physical world. Nonetheless, I’m keeping my eyes, ears, and mind open.

What I read this month

1. Body Futurism by Tony Shorin

   I resonated with this take and hope it is the future that actually unfolds, but I’m more pessimistic that most of us will continue to be mind-heavy and live in our heads. This piece does confirm what I’ve envisioned for my own life: time outside, moving (and feeling) my body, and as much in-person leisure time with friends. Grateful to have surfing, skiing, hiking, backpacking, running, biking, yoga, Hakomi, and more 🙏. Hopefully I’ll be able to visit Esalen at some point this year.

2. Ten years sober by Alex Olshonsky

   An enthralling, harrowing reflection on what it’s like to suffer from addiction. As I was reading in the comfort of my apartment, I had to pee so bad, but I wouldn’t go until I got to the very end. The sheer intensity of addiction was eye-opening to me. I had lunch with Olo in 2024 and he’s completely turned his life around in a way that continues to inspire me.

3. The Patriot by Jeremy Stern

   A long piece on Shyam Sankar, CTO of Palantir. With how chaotic and polarizing the world seems to be these days, I appreciated this profile of a real human at a controversial company. It’s a reminder to refrain from holding hot beliefs on individual people or entire organizations without taking the time to understand them first.

4. Excellent Advice for Living by Kevin Kelly

   Kevin Kelly is a modern sage who despite having obtained conventional success, got there without having to grind the rat race or compromise his values - many of which I can relate to. His latest book is an easy read of bite-sized wisdom. I noted the ones that hit me like a loving twack from Mr. Miyagi in Karate Kid or Master Oogway in Kung Fu Panda:

   1. You don’t need more time because you already have the time that you will ever get; you need more focus.

   2. Don’t create things to make money; make money so you can create the things. The reward for good work is more work.

   3. If your goal does not have a schedule, it is a dream.

   4. Don’t ever work for someone you don’t want to become.

   5. Figure out what time of day you are most productive and protect that time period.

   6. When you find something you really enjoy, do it slowly.

   7. Art before laundry.

Intentions for March

1. Find my writing rhythm again. Process > Outcomes.

2. More movement. It’s getting warmer here in Palo Alto. We spring forward on the 8th and then the sun will set at 7:30 or later. The sun is out and I must go.

3. More unscheduled “Me time”.

4. More internal stability. The outside world is getting crazier and more volatile - at least that’s my perception. I’ll meet it with more chill vibes from the inside, hopefully.

Glancing outside and downwards towards the ground, there’s snow on the ground, which is dangerously low for this time in the season. I’m sipping a zero calorie cream soda and have three tangerines sitting standby for consumption. I’ve been reading the memoir Wild, about a woman’s journey through the PCT, but ten pages in, and I remember how scarce time to write has become, so I shut the book and grab my laptop.

I would love to have the time to read more, write more, stretch more, and in general chill more, but my days so far have oscillated between work and skiing with little breathing room.

Life is intense and simple right now. I have less anxiety but more stress. It can be overwhelming at times, but it’s also been fun to live this familiar way again. Even though I have a lease now, I still believe in seasonal living, matching my personal rhythm with the environment around me. I’m currently in a go-go-go season, and in a few weeks, things should slow down a bit.

The early bird gets the worm

I started waking up earlier, and it’s awesome. If most people are morning birds or night owls, I’m definitely the former. Now that I work a full-time job again, I’ve realized that the only way to get my personal stuff done is to do it outside of the work day. Back in 2019, during my first job, there would be weekdays where I would only remember ever working, nothing else. I’ve since learned to side-step the false dichotomy of putting myself first versus following through on my work responsibilities.

At 5:30am, after I’ve chugged a glass of water and meditated for anywhere from 5 to 15 minutes using Insight Timer to keep my streak going, I plop down at my dining table and proceed to indirectly stare into a light therapy lamp emanating 10,000 lux of brightness. It works. After journaling and reading for a bit, there’s a sense of momentum, like one thing just rolls into the next. By the time I start working, I’ve already lived a mini day.

Experimenting with time

We’ve all experienced how time isn’t linear. Being in the DMV line feels different than surfing a wave or skiing a steep line.

With less free time and more constraints, I’m learning how to expand time rather than just manage it. Waking up early is the unlock. When I start the day with meditation, journaling, and reading before anyone needs anything from me, the morning stretches. It’s a kind of healthy selfishness, claiming the first hours for myself before giving the rest away. The workday is simply an addition, a large one, but not the whole thing.

I’ve had to adjust to more structure and not always having total control over my time. This is my way of flowing with the constraints rather than fighting them.

Reading is fun again

When I was a kid, I used to devour books like My Side of the Mountain, The Hardy Boys, and The Boxcar Children. I could sit, whether in a chair or on the ground in pretzel formation, and read with the focus of a sniper for hours. Maybe it was school, social media, or work, but I lost that spark at some point. I stopped reading for enjoyment when I was forced to read for class, or when more addicting alternatives dominated my attention.

It’s been a practice to reclaim my attention. I think I had to sober up from social media before I could get back into reading again.

This month, I read Matthew McConaughey’s Greenlights which was an epic read of absurdity and a refreshing look inside the famous man’s life. Then I read Draft No. 4 by John McPhee. To read a book about writing was quite meta, and I noticed myself picking apart the word choice, structure, and rhythm, occasionally how even though I’ve improved as a writer, there’s still many levels to this.

No longer am I forced to read, and that has made all the difference.

Work

The role of a product manager is evolving quickly. In terms of timing, I left my previous full-time job right when ChatGPT first launched at the end of 2022. Until three months ago, I wasn’t working in tech, which means I missed the toddler stages of AI development, only to join right before Anthropic released Opus 4.5.

Even though my full-time jobs have always had the “product manager” title, there’ve been some new adjustments to get used to. With tools like Claude Code, Vercel, and Cursor, I can rapidly prototype new ideas and get customer feedback without involving a single engineer. In addition to product, I’m also spending part of my time on sales and marketing. But I think that’s less due to AI, and more just because we’re an 8-person startup.

There are days that feel intense, but I’m glad to be in this position. From my vantage point of building AI products and using AI tools in the creation process, I can see just how powerful this new technology is, and also its limitations.

As of now, I don’t have any specific predictions about AI. Things are going to get even crazier, and we should brace for change and stay adaptable.

Intentions for February

1. Continue to find my rhythm at work, largely a function of working hard, prioritizing what’s important, nurturing relationships, and taking care of myself.

2. Enjoy skiing this week in Jackson Hole and then next week in Salt Lake City.

3. Less: multitasking, late night work, and dairy (I’m lactose intolerant).

4. More: reading, writing, walking, and stretching.

Hope you all are having a great start to 2026 ✌️

This year was a tough year for me. A beautiful, transformative year with many rich memories, but a tough year nonetheless.

At the start of the year, work was coaching and writing - with zero thought of getting a job. A lot has happened since. I’ve transitioned my coaching practice to part-time and as for writing… as you can tell from my lack of publishing, it’s been tough to prioritize it.

But life has felt really full the past couple months - in a good way.

The big news is that after nearly three years since leaving my last full-time role, I started a new job!

In mid-October, I joined an early stage startup as head of product. My definition of work has shifted once again. My daily life looks radically different, but it’s been a surprisingly easeful return.

Below, I want to relive this year and capture the essence of each month, but I think the contrast of the two bookends captures it well:

I started this year skiing in Salt Lake City, freely weaving together days on the mountain with coaching and writing.

I’m ending this year in Palo Alto, with my first stable apartment in six years, and I have a full-time job again - my first “real” job in nearly three years.

These two major changes, both personal and professional, proved to require more energy and more time to adjust to, but ultimately, for the better. I’m entering 2026 with the most stability I’ve had in recent memory, and with that, I’m moving towards fewer, focused commitments and deeper intentions.

Let’s see how 2025 went…

January

January 1st: I started off the year by staying in the most absurd Airbnb in Salt Lake City with my friend Niles. We enjoyed some nice meals together like hot pot at-home, but what made the experience bizarre was the fact that the owner allowed her three little dogs to dominate the only bathroom on the second floor. I don’t mean they used the toilet - the little creatures would poop on disposable mats laid on the floor.

Later in the stay, I came across a startling discovery: inside the garage were a couple large cardboard boxes shipped from overseas. Within these boxes were hundreds, if not thousands of vape cartridges. Our objective was to remember some amazing days on the ski mountain, but we left with some additional memories.

That was just the first week. Then we moved into our monthlong Ski Haus where things mellowed out a bit. I lived with Brandon, Niles, Andrew, and April, along with nearly a dozen various friends that came in and out throughout the month. I enjoyed the skiing, but also all the accessory activities like Monopoly Deal, the local gym, group dinners, and rolling to hot yoga as a crew. We even saw a Sundance film where we got to meet the lead actors and director!

I also made a visit out to NYC to see my girlfriend. I remember jogging down the frigid Hudson River Greenway in beanies with steaming breath and an amazing meal at the Thai restaurant Soothr. But what stands out about this trip is the choice itself. With just a modest income and the tradeoff of losing a few days of skiing, I chose to go on this quick trip. In the past, I optimized for freedom and tried to maximize ski days. Now, spending money in an almost frivolous way and sacrificing powder days for a long weekend together felt worth it.

February

So much happened in February, starting with the 3rd.

At 6am PT, still lying in bed with the dark sky outside, my girlfriend found out she matched for residency at Stanford. It was her news, but it would reshape both our lives.

I had the brilliant idea to celebrate at BJs. From watching fitness influencers demolish the pizookie on cheat days, I thought it was a nice restaurant (spoiler alert: it’s like Applebee’s, but maybe worse).

Then we headed to the airport for a midnight flight to Beijing. It was my first time back in China since 2019.

I headed to Zhangjiakou to visit my dad’s side of the family. It’s the rugged city near Beijing that hosted all the winter olympics events that required mountainous terrain. For four nights in a row, we’d gather at a large table with the spinning glass turntable and feast on a dozen dishes at once. I tell people my top three cuisines are Thai, Mexican, and Korean, but the exception is Chinese food in China, which takes the top spot. Seeing my cousins’ kids grow six years worth made the six year gap feel quite real. Some went from baby to kid who now speaks better Chinese than me.

I spent a few days in Beijing as an autonomous tourist for the first time. Previously, I’d go with family or some summer program, but I could now book my own DiDi (Uber of China) and pay for things using WeChat or AliPay.

Next, I flew to Hokkaido, Japan’s northernmost island for a weeklong ski trip with nine others. The US already has world-class skiing, but there’s always been an allure to Japow, the deep, light snow that Japan gets from cold Siberian winds and low-moisture snow crystals. Somedays, I’d wake up at 5am for a coaching session before skiing all day and unwinding in the almost-scalding water of the onsen. We could’ve gotten luckier with the weather, but we had one amazing day with not a cloud in sight and at least ten inches overnight.

I reunited with my girlfriend and traveled from Tokyo to Hakone to Kyoto. At a Michelin star restaurant, I ate a macaron that looked chocolate-flavored, but it was actually deer blood. In Hakone, we stayed in a ryokan, and enjoyed kaiseki-style dinners while wearing kimonos. Being near Lake Ashi with Mt. Fuji in sight helped me slow down from continuing my otherwise default mode of fast-paced travel. In Kyoto, after along the Kamo River in the rain, my breakfast consisted of a warm pork bun, protein shake, and three large carrots from 7-11.

In February, I also decided to leave Downshift. It was unexpected, but came with clarity that it was time to move on. Although I had so much development remaining, I felt confident in my ability to coach, and that’s what allowed me to take the next step forward, despite looming clouds of uncertainty for how the rest of the year wsould unfold.

March

I came back from Japan and had time for one last ski trip.

My friend and former roommate Jacky flew in from Vancouver and we headed to Tahoe just in time for a huge storm. We stayed in the brand new Evo hotel and in the morning, they gave us free pastries only for us to end up standing in the KT-22 lift line for five hours. Skiing after a major dump is high risk, high reward. You can either enter mind-warping flow states from gliding through fresh snow or you can wait in line with dozens of other ravenous powder enthusiasts. All that sugar for nothing.

After the final taste of winter, I hesitantly headed back east for what might have been my last time actually living in New York City.

April

Being back in the metropolis that runs on coffee and money accelerated my already brewing hunch that I needed to reassess my approach to making enough income. By this point, it had been nine months since I started my coaching practice, which I started out of seeking fulfillment, with making money being secondary. It was time to take a close look in the mirror and be brutally honest with myself.

Do I go all-in on coaching and make it work financially, or is there another path for me?

Even though I was aware of all the business tactics I could’ve employed around marketing myself better, it just didn’t feel aligned to try and push my way through. It was weird to question my own intuition - like what if this was sports practice where I just have to keep running enough suicides and shoot enough free throws to make it to the next level. Persistence, discipline, and grit are all important, but here they didn’t feel entirely relevant.

I stumbled into coaching, and while I certainly fantasized about it supporting me financially, my actions didn’t reflect someone who was hellbent on creating a thriving, independent business. I wasn’t aggressively marketing myself or reaching out to people who I could see myself coaching. In hindsight, I was pursuing a passion. A passion that I was taking seriously and love doing, but without the commitment and determination for it to be my job. Accepting this lagged behind and took some time for me to see clearly.

I started to think about what I’d do to make a stable, healthy income again and I became excited about joining one of the several mental health tech startups out there. It made sense to me - I wanted to combine all my skills and interests in tech, coaching, and somatic therapy to help more people. I interviewed for a role that I thought I’d be a perfect fit for, and didn’t even make it past the recruiter screen. In the past, this person would be cold emailing me to join, and now I couldn’t even get past the first round. What made it sting even more was that through connections at the company, I knew who the hiring manager was. It was a former climate founder who once asked to chat with me, back when I wrote deep dives on climate tech. I bookmarked this as evidence for how much I value reciprocity.

Later in the month, I had breakfast for the second time with Tom Morgan who asked me if I’ve ever considered starting my own community. Some time later, a new friend I had just met asked me the exact same question. (This is relevant for later.)

I started training for the 1,000 pound club. The first step was repeating the process of finding a gym, something that I had become unusually good at from all my past sublet stints.

May

I went back home to the Bay and spent a whole day touring apartments in Palo Alto, which made the impending move all the more real. From 10am to 4pm, I had back-to-back apartment showing every 30 minutes. At each place, I would record a video walking around and then immediately after I left, I would send the video and a voice note describing my thoughts to my girlfriend who was still on the east coast. After all the showings, my top two were a tiny house wedged between two $10 million homes in the wealthiest part of Palo Alto and a humble apartment complex that had fresh air flowing between buildings and a park right next to it. We ended up at the latter.

I drove up to Mendocino for a retreat with a conscious entrepreneurship community I belong to. Many people were more successful than me on a professional level, and also further along their spiritual paths than me. I hadn’t seen firsthand the material and spiritual worlds interweave with each other, so this expanded what I thought was possible in a refreshing way.

Life sped up again.

I asked Claude how to adjust my strength training schedule if I wanted to hit the 1,000 pound club even earlier than already aggressive target.

A couple weeks later I hit my goal. It was satisfying to accomplish, but felt more like a checkbox that had been crossed off. The process itself of increasing the weight and getting stronger week after week was far more enjoyable than that final day of maxing out. Setting the goal itself was necessary to coordinate my willpower to focus on a singular objective, but it was actually the cliché journey that mattered more.

I flew back to NYC for my girlfriend’s graduation from medical school. At midnight, I flew to Rome.

I stayed in a hostel before my girlfriend joined me - partly to save money, partly curious if I could still enjoy it. The hostel’s dinner ranged from zero to ten euros, depending on the dish. I joined for the first night’s “rice salad”. Pretty mid, but not bad for $0.

We roadtripped from Rome to Florence and stayed at a farmhouse midway. The host Laura prepared a simple yet extensive breakfast spread every morning that we ate outside overlooking the Tuscan hills. I get a taste of what people mean by the slower, simpler living of Europe.

While in Saint Peter’s Basilica, I experienced a great wave of awe as I stroll around. It’s rare for me to experience the sensation outside of being deeply immersed with the natural world.

June

After Italy, I flew to Asheville for the onsite component of my Hakomi somatic therapy training. I met my teachers and fellow trainees for the first time in-person after spending hours on Zoom together. Our Airbnb had no kitchen, but the retreat center was close enough to walk to, where Dennis and I made oatmeal and eggs every morning. At that time of year, the park next to us was overflowing with greenness.

On June 20th, we moved in to our apartment in Palo Alto. The first night we slept on a mattress on the ground. It would be another couple months before our dining table and my desk could be upgraded from plastic white foldable table to something more permanent.

I made it to a final round interview for a role that genuinely excited me, but didn’t get the offer. Immediately after, I felt pangs of regret, frustration, shame, and anxiety. The next morning, I woke up and got back to work.

July

My friend Parker visited, which is great timing because I’ve already bought a couch from on Facebook Marketplace, but need help retrieving it with a U-Haul.

I cycled through trial gym memberships, hesitant to sign a contract. It mirrored my inner state: I had arrived in Palo Alto, but didn’t feel settled in yet.

I joined nine other men on an intense backpacking trip in the Eastern Sierras. It was epic.

August

We host a pool party BBQ at our place, gathering up existing friends and meeting new faces as well.

We go on a weekend trip to Tahoe with friends. We hike, kayak, spikeball, play Skull King, and devour an entire watermelon within a few hours.

I start training jiu jitsu at the gym across the street. After the first session, I walk home feeling fully alive in a way I haven’t felt in months. My shirt is drenched in sweat and feels noticeably heavier.

September

I realized I’ve been feeling lonely from being at home all day and pay for a library card at Stanford. I start spending more time on campus and seem to benefit from the residual youthful academic energy.

After seven rounds of interviews over the span of eight weeks, I got rejected by another company. It’s frustrating because now I have to start all over again.

I logged my learnings and vow to myself that I will somehow make the third time the charm. I begin interviewing with several companies.

I was supposed to go backpacking in Yosemite with friends, but we changed our plans after forecasts of torrential thunderstorms. Instead, we head north and camp just two miles away from the trailhead. It was far more chill than past trips and the people became more of the focus than the scenery.

During a weekend of Hakomi training, I had a powerful experience during a practice session where I’m the client. I visualized attempting to offer gifts of flowers but keep seeing an axe chop off my arms as I extend forward. It’s only when my therapist tells me that he’s also reaching forward to receive that the axe surprisingly doesn’t swing down. As the visual evolved, I also realize the mysterious axe looks cartoonish and that my arms regenerate like a gecko. I interpreted this in the context of my job search: that the axe is actually benevolent, the suffering is optional because my arms regenerate instead of bleed out, and that there will soon come a time when my offer is genuinely received.

October

It was my girlfriend’s first week off from residency, which was requested and planned months in advance. We decided to go to Hawaii, which wasn’t an easy decision because it would be smack dab during the later stages of interviewing. Our first day was also my birthday and we celebrated at Thai Temple. The next day was Mid-Autumn Festival and we celebrated with friends and mooncakes. Jackie and David got engaged recently. Ted and Yan are only in town for one night as they make their way to Asia for a seven week trip. We hung out with Tracy and Loren who also closed on their new house in Diamond Head that same day. The house itself needs a lot of work, but I get excited for them as I visualize the possibilities.

I finally got a job offer - ironically while I was vacationing. There was a huge relief and the next day I catch a fun wave on the North Shore.

I started the job and on my 7th day (Sunday), I have Hakomi training from 7am-1pm, then I hit the gym, come back and play tennis with my girlfriend for a bit, then Uber to the airport to fly to Vegas. I check in to my hotel and then have a Zoom call with my CEO to gameplan the conference. This one day symbolizes my new identity and encapsulates my new priorities.

I spent the next two days in Vegas non-stop approaching strangers and slinging B2B SaaS. It’s tiring, but surprisingly fun.

I also launched Free Agents, a community for multidimensional people seeking beyond the conventional path. The name comes from this blog post where I propose a third option of worker identity to side-step the false dichotomy of missionary vs. mercenary.

Free Agents is unfolding to be a fulfilling project where I can facilitate deeper questions and support people, but there’s also a lightness and playfulness that I see less often in communities. It also helps that most of the people that are in it started out as friends first. It’s an eclectic mix of people, ranging from skateboarder dads to surfer models to former White House Oval Office staffer.

Going into this project, I teetered between making the community more focused on transitions or to try and make it an actual source of income, but ultimately followed the question “How can I make this more fun for me?” Going this route led me to designing it lightweight (we only meet once a month) and for free.

November

November was a blur. A good blur, but also the shorter days made me feel like I had less energy.

I transitioned my coaching practice to part-time. This meant “graduating” a couple clients who I had been working with for over a year and asking others to fit into my now rigid schedule. You see, in taking this new job, I was also not willing to stop coaching. For me, coaching has become this part of me. It’s something I make money from, but that’s not the main reason why I do it. I also knew that the only way to truly be committed to the new job was to keep coaching outside of working hours. I was glad that every client was willing to accomodate my new 8-9am PST constraint.

The intensity took getting used to. Multiples times, I would have a coaching session or a customer meeting at 8am, then work for a full day, and then roll at jiu jitsu from 6-7:30pm. I’d work a bit at night and then go to bed.

I started nesting. I bought furniture and spent a few hundred bucks to print out my photography, which felt weird after years of minimalism. I had to double check with myself if these were purchases worth it to me, and they were.

We hosted Friendsgiving and made use of our dining table that I bought from a grandpa in Redwood City. It has two leaves that extend to seat up to 12. I paid him $150 and it took me two trips to haul everything home. Our neighbor Jeff had to help me carry the tabletop up. Everyone brought a yummy dish, but Geo’s Thai steak salad and Sophie’s rosemary rice crispies stood out. Robbe somehow dropped $100 on mashed potatoes and gravy at Whole Foods.

We celebrated Thanksgiving with my girlfriend’s parents who came and visited us. Our Thanksgiving dinner consisted of a dozen delicious Chinese dishes. I’m glad I didn’t have to attempt a turkey. We took a daytrip to Monterey and Carmel-by-the-Sea, stopping at a farm stand to buy pomelos, grapefruits, persimmons, and pomegranates. While eating these fruits on a picnic table by the ocean along 17-mile drive, I gazed at the waves that were crashing on shore. I realized I sort waves into too mellow, just right, or too big depending on how surf-able I think they are, no matter whether I’m there to surf or just to watch.

December

I ended the year strong. I started to find my groove at work, but am still slightly tired.

We went to Marin for a weekend getaway, but also to kick off the annual reflection. I’m used to early morning and late night drives to save money on lodging, so this staycation felt like a splurge. Not having to drive back meant that we could enjoy the sunset at Mt. Tam and avoid having to cram everything into just a day trip. We watched the newest Knives Out at the Airbnb. I am both glad that we don’t have a TV at home and that we get to watch the occasional movie when we’re traveling. It feels like a treat.

The next weekend, I flew to Denver to ski with Parker. I took the early morning flight and took the train into downtown to work. The skiing itself wasn’t that great because of the snow, but we made the most of it. We watched the half-pipe Olympic qualifiers at Copper and played board games at night. I lost in chess to the rapper Logic’s chess coach.

We find out that my girlfriend has December 24th and 26th off, creating the conditions for a possible surprise 5-day trip. It felt like a lucky gift given she only gets four weeks off a year and they have to be requested a year in advance. I check the weather in Tahoe, Utah, Colorado, Washington, and even all over Canada, in search of any signs of sufficient snow.

After factoring in flight prices around Christmas, Utah seems like the best option. As we’re driving around, skiing, and eating out, past memories re-emerge. We go to this $26 AYCE hot pot restaurant on Christmas Day and they’ve since renovated the entire place. They also raised the prices by $2. At Alta, I point to runs I’ve skied before like Alf’s High Rustler and Big Chute on Mt. Baldy. It’s the same places, but I’m experiencing it in new ways.

My 90-year old grandma was hospitalized four times over the span of two weeks so I went back home. She’s stable now, though her vitality will likely never fully return.

The last few days of the year arrive and I finally start writing again.

Reflections

Books

This year I read 14 books. I also started, but didn’t finish another 14.

On Becoming A Person by Carl Rogers taught me the importance of being authentically myself. I started reading it to help me as a coach, but the ripple effects have applied to my writing and how I show up in my relationships.

I got back into fiction, reading The Da Vinci Code and The Three-Body Problem. I tried to get into heavier reads on spirituality and consciousness, but I wasn’t in the mood.

I ended the year with Endurance, the story of the Antarctic shipwreck where the entire 28-person crew survived for over a year before being rescued. Books like this - survival stories and dude-on-adventure narratives like Barbarian Days and Into Thin Air - capture the human condition at its most intense. They fuel something in me. I want to read more of them this year.

Reviewing 2025 Goals

I’m reviewing goals to learn about myself and get closer to my truest desires, less as a measurement for how good I am at doing things.

Make more money: I wasn’t sure how this would unfold, but I’m happy with where things are landing. I’m enjoying the job: the people, learning about AI, playing a role within a team, and the financial stability.

Create authentically: I intended to write and make videos. I didn’t make any videos and feel completely okay with that. I wrote blogs I’m proud of, like I Am Just A Dude, The Ski Haus, and Young Person Energy. More importantly, I stopped writing as a coach and started writing as a person. I stopped approaching with the pre-writing lens of how to make it sound like a coach wrote it, and instead listened more closely to what I actually wanted to write about.

Spaciousness: This goal was too vague to hit or miss. I wish I had more unscheduled mornings, but my actions reflect a tendency to maximize my days. I get overwhelmed often, but I also end up experiencing life to the fullest. This year, instead of spaciousness which is about boundaries and emptiness, I’m focused on creating more time by increasing my energy.

Depth: The big step here was enrolling in a yearlong Hakomi training. But I think about depth differently now. It doesn’t need its own goal slot. Depth comes from welcoming it in daily life, even when uncomfortable. This year I plan to work with a Hakomi therapist, less to heal something broken and more out of curiosity about the unconscious patterns I carry.

Lessons Learned in 2025

Transitions take longer than you think. The Gregorian calendar creates the false narrative that things can be compressed into one year periods. In my case, it’s been closer to three years. Four if you count the year it took to quit my job.

Let go of what is not essential. I eased off of coaching needing to provide me full-time income. Now I don’t have that pressure, and I do it out of love and fulfillment. I also see other ways to serve people without needing to call it coaching, whether through Free Agents or just being there as a friend.

Big moves take more energy than you think. I went from six years of nomadic living to putting down roots in Palo Alto. I moved in with my girlfriend, in a new location, in a new home. It took significant time and attention to feel actually settled, but once I got there, it’s been smooth sailing. It’s nice not having to find a new gym, grocery store, and apartment every month.

My core values changed.
Previously: Creation, Creativity, Health, and Curiosity.
Now: Genuineness, Health, Curiosity, and Adventure.

I removed Creation and Creativity because they’re not essential for me. I don’t have to be putting things out there all the time. There are seasons for it.

Genuineness is now my top value. Being authentic, keeping it real. It’s what has led me to pursue a constellation of seemingly unrelated projects, except they actually are related because I am the source of all of them.

Health remains because it supplies the life energy that keeps me going.

Curiosity remains too. Curiosity guides me to interesting places, even when I can’t see exactly where I’m going.

I added Adventure after rooting down this year. I used to have built-in adventure from living nomadically: Hawaii, ski towns in winter, NYC. Now that I live in Palo Alto, I need to be intentional about creating it myself. I’m aiming for at least one adventure each month, whether a day trip to surf in Santa Cruz or a two-week ski road trip to Wyoming and Utah.

I experience the world most deeply, when I am doing something adventurous - with all my senses activated. The initial imagery I get is surfing a heavy wave or skiing a steep line. But adventure isn’t exclusively about outdoor sports. The essence is being at my edge, yet with a foundation of safety. I also see the thrill in committing to ambitious goals and surrendering to what happens.

Money is necessary, but not as important as you think. My relationship with money feels healthier now. I see it more clearly: what it can provide me, and what it can’t.

I spend liberally on what I genuinely enjoy, like ski trips at the best mountains, but find creative solutions to make it affordable. In Colorado, we split a two-bedroom loft among eight people. It made for a cozy vibe. In Utah, we stayed in a shared Airbnb with the host and still got our own bedroom and bathroom.

I’m aware that lifestyle creep is a thing, and hope to get ahead of it by being content with a one-bedroom apartment for the next couple years. I’m also firmly against being a two-car household given how easy it is to bike around Palo Alto. Sometimes on weekends we bicker over who gets the car, but I’d rather practice compromising than cave into convenience.

The life I want with more money isn’t that different from the life I loved with less.

I don’t want to slow down. A common idea in personal growth is that doing less leads to being more. For the last few years, I followed this path. At some point I had a morning routine that might’ve lasted over 90 minutes. That approach no longer resonates. I see how these are all tools and practices to serve me, and that there’s no one right way to live.

I aspire to have the presence and gratitude of a Buddhist monk who smiles big after biting into an apple. But I also want full days. Radiant, dynamic. Not burnt out, but like an athlete in season, or an animal that knows when to migrate and when to rest.

The essence of my being is playful, childlike, and adventurous. I care about a lot of things and recognize the preciousness of this time in my life: I have enough wisdom to know what’s important, the resources and independence to do what I want, and the youthful energy to keep at it.

I no longer view maximizing stillness as an actual objective.

Intentions for 2026

This will be the first year in a while that I’ve had a stable job, my own place, and a partner. I’m not used to this level of groundedness, but it sure is nice. I intend to build on top of this stable foundation.

Instead of concrete goals, I aspire to embody a particular energy.

I want the next few years, the last few years of having the privilege of being child-free, to be the years that I worked the hardest.

I want to be disciplined to my craft. Somerset Maugham said, “I write only when inspiration strikes. Fortunately it strikes every morning at nine o’clock sharp.” Instead of just bite-sized blogs, I will pursue a major project of my own.

I may have returned full-circle back to a similar job, but things are fundamentally different. My perspective has changed. My whole identity isn’t in this job, yet I care more than I thought I would. Doing well and contributing in my new role made it into my top three goals for the year. I want to genuinely level up as a startup operator building at the frontier of AI. When it comes to work, across all fronts, my goal is to keep caring. Avoiding work only delays the inevitable and drains energy in the meantime.

When it comes to my health, I’m a couple pounds fatter than my best and my hips are tighter than I’d like. There’s an abundance of good food around me, but the most satisfying meals are when I’m a particular kind of hungry: after sustained effort on things I care about, whether intense physical movement or deep work on projects. In 2026, I’d like to prioritize nourishment over indulgence.

I feel older, I am older, but I still want to retain my sense of youthfulness. Going on adventures is how I’ll stay young. I’m seeking the simple, spontaneous adventures that bring out my childlike energy, which I want to preserve.

To aid me on this quest, I’ll simplify. I’m willing to tradeoff cooking proper dinners so I have more time during the week. I’ll go to the library so I accumulate less clutter. My investments are on auto-pilot. I’ll be okay with keeping up with fewer people. I’ll say no to good opportunities to preserve space for the great ones I’ve already committed to.

Last year, I followed a lot. I was waiting until February to find out where my girlfriend matched, which determined where we would live for the next six years. Then we were both waiting to move in. At times, I had to wait for something else before I could keep going. That was a practice in itself. This year, I don’t have those constraints. I can choose to do what I want more often now. It’s not purely selfish. It’s freedom. And often with the freedom, I still choose to be with others, to help others.

During our final coaching session, a client told me how much I helped him over the last year. From the Free Agents calls, I see how people feel a sense of kinship and permission to dream big. Yesterday, while standing by a bonfire on the beach, someone who reads this blog told me that my writing feels like the opposite of watching YouTube.

Even though 2025 was the year I put my full-time coaching pursuit on pause, it’s also the year I end feeling stronger and with a greater sense of purpose. I’m ready to play.

Even though it’s a ritual dictated by the government, it’s still a ritual nonetheless. I’m excited because my mornings will include less puttering inside, waiting for the sun to come out before I walk around the park behind our place. But I’m also kinda sad because it’s going to start getting dark at 5pm.

Combined with the changing colors of the leaves and a recent big transition in my life, I’m finding myself prematurely looking back on this year, and already anticipating the potential changes for next year.

Fall has become a cherished shoulder season for me. As playgrounds of mountains and forests shorten their hours of operations, it’s a good time to recover from the long summer days. For some people, winter is the designated season of rest and reflection, but as I’m anticipating intense bouts of weekend warrior syndrome on ski slopes, now is a good time to slow down and do less.

I greatly underestimated the amount of energy it would take to feel at home here in Palo Alto. It’s one thing to move from one apartment to another in the same city. It’s another thing to move across the country to a new place, move in with your partner, buy furniture for the first time in five years, make new friends, and figure out your career all at once.

We moved here 4.5 months ago, and even though we’re still iterating on the apartment furnishings and layout, I’d say we’re pretty settled in. The way I’m measuring this highly subjective quality is based on how much mindspace I’m able to outsource to routine. The more I’m able to definitely say “Mondays are for jiu jitsu and solo dinner”, “Saturdays are for basketball and chilling”, and “Sundays are for Costco runs”, the more settled I feel.

In the past, knowing what I’m going to do tomorrow would terrify me. It’d feel like succumbing to the grip of monotony. A younger version of me, would be excited about waking up in a new sublet, eager to walk around a new neighborhood, and “play by ear” every moment. Now, it’s the complete opposite — I find it weirdly satisfying that my grocery list is pretty much the same every week.

For this month, I’ll recap my trip to Hawaii, what I learned about friends from the British anthropologist who has a number named after him, and what it’s been like living in Palo Alto.

Hawaii

Since I stopped living in Hawaii, I’ve maintained my annual pilgrimage. This time around was a balanced blend of familiarity and novelty. We stayed at my friend’s place where I first stayed at in August 2021. Our first meal of the trip was at the Thai temple, a weekly Sunday ritual back when I was living on island. I surfed at the same spots (Canoes in Waikiki and Lani’s on the North Shore).

Compared to last year’s trip, this time was less planned, slower paced, and captured more of Hawaii’s relaxing, communal energy. I even told myself “It’s okay, we don’t have to do everything.”

We’re happily rooted to Palo Alto for the next several years, so while the daydreams of living in Hawaii are on pause, I could at least reflect on what I wanted to bring back with me.

Two things that stood out: simplicity and community.

In Hawaii, good times don’t have to be fancy. Before we went out for dinner on our final night, we went for a sunset stroll around Magic Island beach park. There were so many different groups of people jogging, walking, or sitting on the grass. What stood out was just how many different picnic blankets I saw, some with full-on barbecues and coolers, others taking it easy with take-out, and some with no food or drink at all, just the presence of company. I love a nice meal out with friends, but I also don’t want to be overly reliant on the veneer of fanciness to have a good time. I hope to maintain the reassurance that as long as I’ve got my people and a picnic blanket, I’ll be good.

Being on an island, you end up seeing the same people over and over. I experienced it during my morning walks, surf sessions, and yoga classes. This shared consistency is a positive feedback loop — you’re more likely to say hi to your neighbor or spark a conversation if you know you’ll see them again. One of my friends has come to know his neighborhood so well that he often adds 20 minutes to his errands in case he bumps into a neighbor on the sidewalk.

On the mainland, “small talk” refers to the trivial chatter before you get to the real stuff, the meat of the conversation. In Hawaii, “talking story” might refer to the exact same topics and words, but it takes on a more significant role. It’s a way to stay connected to community and be available for each other, where our attention and time is somehow just as valuable as the meeting agenda — something that we don’t always remember in modern corporate culture.

When I was a product manager working in a fully remote role with teammates all over the world, we just immediately jumped into the “real stuff”. In hindsight, the lack of knowing people beyond their Slack profile and tiny face with blurred background on Zoom certainly contributed to the job feeling meaningless. It wasn’t just the product that we were building and mission we were pursuing, but the internal process of how we worked with each other that sapped my soul.

Friends

Assuming you’re intentional about choosing what you read, you can think of your current book as a reflection of what you’re looking to learn. Over the past few years, I’ve been mostly interested in self-help and personal growth books that err on the side of deep, spiritual, and individualistic. But recently, while at the Palo Alto city library, the book Friends by Robin Dunbar caught my eye.

It was probably a combination of having recently moved here, and being in search of new friends, and having heard of Dunbar’s Number before. It’s the cognitive limit to the number of stable relationships a person can maintain.

Reading an entire book by Dunbar not only cemented the legitimacy of 150, but also revealed the importance of friendships.

The first couple chapters are dry, but that’s so Dunbar can spend this time going through comprehensive research that all triangulates to 150, and the concentric circle model:

First, Dunbar presents research across human communities over the span of civilization, showing that whether it was early nomadic tribes, medieval kingdoms, or cities post-industrialization, we all organize to roughly the same size groups. Then he takes a biological lens to it, evaluating brain size across primates, showing that the number of relationships we can maintain is tightly correlated with brain size. Finally, he points to contemporary examples across the military, corporate org charts, and Christmas card lists, demonstrating that even in modernity, this ~150-person limit emerges naturally across different domains.

At this point in the book, I was pretty convinced of a natural limit to the number of relationships we can maintain. But so what?

Understanding that there exists a limit made me feel reassured about focusing on existing friendships while being open to new ones.

I didn’t count or sort people into categories like “inner circle” vs. “close friends”. But I already felt the overwhelm of being in contact with than 150 people. This is less me claiming that I’m popular and more a matter-of-fact observation that if you have some combination of Instagram, Twitter, LinkedIn, Substack, and other platforms, you’re likely interacting with far more people than your brain can manage.

The nourishment and connection from the typical online interaction can’t compare to the in-person analog. The physical touch, synchronized movements, and shared emotions result in bonding at the neurochemical level that can’t be created in the virtual world.

The reality is that nurturing relationships is time-consuming and requires effort. The amount of time that apes spend grooming each other is directly correlated to the closeness of the relationship. There are constraints with how much you can groom as your group size increases, especially when the time spent grooming could be time spent foraging for food. Dunbar proposes that humans evolved from physically grooming each other to “vocal grooming” through shared conversation and laughter, which releases the same endorphins.

With all this in mind, I’ve gradually and intentionally reduced my online time so I have more time for in-person activities and relationships. I check Substack Notes and Instagram less than once a week. I stopped using Twitter entirely and deleted the Signal app.

It’s been surprising how little I’ve gone up to San Francisco. We moved here four months ago and I’ve only been to the city four times. Having a strong sense of community here in Palo Alto — the kind where I know my neighbors and local businesses — requires more time in Palo Alto, not SF 45 minutes away.

Dunbar also explains how men and women bond differently: women bond through conversation and emotional disclosure, men bond through shared activities. “Women bond face-to-face while men bond shoulder-to-shoulder” resonated after backpacking in the High Sierra this summer with ten other dudes. In Palo Alto, I’ve been meeting people through jiu jitsu, basketball and hosting barbecues. It seems straightforward — doing activities that I enjoy and making new friends along the way.

The final takeaway is how essential relationships are for general health and wellbeing. Strong friendships are more predictive of longevity than obesity, smoking, or lack of exercise. They also protect us from chronic pain, depression, and anxiety. I first got into coaching because I saw it as a way to learn how to live a good life while also helping others do the same.

This book reinforced something important: friendships deserve the same attention I give to individual practices. As much as I value deep practices like 1:1 coaching, therapy, meditation, and breathwork, I used to view friendships as something we all just have as a natural part of life. Now I view having abundant healthy relationships as truly foundational and irreplaceable by individualistic practices, even though those practices are often perceived as more meaningful or higher status. In some circles it’s somehow cooler to talk about expensive wellness retreats than going fishing with your homie. It might seem ironic for a coach to have these thoughts, but I see a place for both: the primal, essential nature of friendships and the intentional work of healing and transformation. It’s not that you have to choose between a meditation retreat and having friends. But if you feel lonely, you might find more relief by spending time around people, calling a friend or family member, trying a new hobby, asking for help, or helping others, rather than immediately seeking out coaching, therapy, or an ayahuasca retreat. It’s important not to conflate one for the other.

Palo Alto

Throughout five years of living without a lease, I watched a lot of tiny house and vanlife videos, appreciating the thoughtfulness and creative use of small spaces. I’m learning to have fun with the constraints of 750 square feet.

Our one-bedroom apartment is good enough for the two of us. Being okay with what I have is a practice in knowing what is enough. I’ve undertaken this small side quest to not only be okay, but actually fully appreciate having a one-bedroom apartment. I want to hold onto this feeling of satisfaction. I know having kids will change things eventually, but that’s not happening anytime soon. In most places around the world, from rural village to big city, this would still be considered large.

There are details I’ve come to love: separate sinks and separate closets to avoid butting heads with each other. Top floor with higher ceilings and a sunny patio for only $50 more a month. An outdoor closet for all my outdoor gear. The stairs that open directly outside have meant that bringing up furniture has been a pain, but we also immediately breathe in fresh air, rather than having to traverse a hotel-like hallway and elevator.

Since neither of us had any furniture to move in with, we’ve continuously iterated on furnishing our home, which has been a low-stakes way to practice noticing how we feel in relation to our space - then seeing what changes would make it feel even more homey.

When we first moved in, the property manager kept pointing out where our movers could park. We didn’t hire movers or even rent a U-Haul. All we had were suitcases and a vacuum-sealed mattress in our SUV.

On our first night, we slept on just the mattress on the floor. We also had two white plastic foldable tables, one as a makeshift desk and the other as a dining table.

Each week brought a new addition. A couch meant we could finally have people over. A rug meant sitting on the floor became a thing. Plants given away from various curbsides brought our patio to life. (two large succulents and a dragon fruit sapling).

We didn’t let a semi-furnished place get in the way of hosting gatherings. For a brunch, we all ate on the foldable table with only two foldable chairs and an orange plastic chair I picked up from a nearby house with a giant FREE sign. I asked a friend to bring two extra chairs. We were short one chair, but luckily my other friend always keeps a camping chair in his car.

We wrestled with getting a TV. Pretty much every home, apartment, or Airbnb I’ve ever lived in has had a TV, so why wouldn’t we get one ourselves? By not rushing to buy one, I could see how often we would actually watch shows on our laptop. It wasn’t that often. Amidst my girlfriend’s intense hours at the hospital, when we did have time, we usually had a meal together, talking, or went out for dessert. After a couple months, I felt confident that even if we did have a TV, we wouldn’t use it much. I can barely keep up with blogs, podcasts, and books, despite staying off social media and ignoring the news. Deciding to not buy a TV felt right. We repurposed the space for two lounge chairs around the coffee table facing the main couch, reflecting my preference for friends over screens.

What makes a place feel like home is having rituals - recurring intentional activities that feel meaningful - combined with feeling connected to your surroundings.

Twice a week at 6pm, I go to jiu jitsu. It’s a nice forced end to the workday. I notice by 5:30pm I feel pretty tired, which comes with the brief resistance to going, but I always walk back home in the dark feeling energized and awake.

On the weekends, I walk down the street to Covour Coffee and have started to see the same people. On Halloween, my friend and I were waiting outside for Thai food next door to be ready for take-out when we started chatting with the baristas who were giving out hot chocolate and candy while projecting a Halloween movie outside the cafe.

I walk around the park right next to us and see the same dogs in the dog park, the same dude hitting a tennis ball against the wall, and the same elderly Chinese couple practicing qigong. I notice the colorful trees, particularly the ones with leaves in a green-red gradient. It’s a nice way of marking the passing of time.

I’ve been consistently swimming once a week, usually on Sundays at the Stanford pool. It’s rejuvenating to soak up the sun while in the water. I don’t even do it for the exercise. I’m not a fast swimmer and I only swim for 20-30 minutes after lifting.

Making new friends and finding a new flow have helped me get settled in to my new home, but I don’t have it all figured out and am still looking for ways to feel an even greater sense of belonging here.

It’s still odd that as soon as I walk off of the apartment complex, all the homes are insanely expensive, ranging from $3M for a two-bedroom dinky house to $5M recently renovated four-bedroom. After reading Friends, I’m trying to meet more people in the area, understanding that strong relationships are more likely to come from in-person friends as opposed to online buddies.

So far, the newness of jiu jitsu and reuniting with my childhood passion basketball have kept my thirst for stoke quenched, but I suspect that at some point this quiet town with temperate weather and flat roads will start to feel almost too comfortable. Then I’ll start looking for ways to incorporate more adventure in, whether it’s surfing, running, or cycling. Or I’ll go completely the opposite way and get a dog.

For this next month, I’m focused on:

• Getting settled into my new rhythm (more to share in my next blog).

• Starting to train for ski season (more stretching and starting to add in leg blasters).

• More solo time to read and write.

• Easing off the resistance to the big sleeps. I’ve been getting 9 hours of sleep a night and I feel like I need it.

If you made it this far, thanks for reading! Let me know what resonated in the comments.

Young Person Energy exists in all of us, lying dormant through our teens. But starting in college, with the help of a side job or internship, it becomes unleashed. When you’re without cash, you’re just dreaming, and without the freedom, you’re stuck at home. But once both conditions are satisfied, previous fantasies become possible realities.

Young Person Energy isn’t a strictly physical energy. It’s the type that allows you to wake up at 4:30am, drive 3.5 hours to Tahoe to catch first chair when the ski resort opens, ski all day until 4pm, drive back, stop for In-N-Out (two double-doubles, plus a protein-style hamburger for health), and then stay up until 3am partying.

Or the energy to backpack Southeast Asia with five other dudes for three weeks, changing hostels every 1-2 nights, riding mopeds by day and slamming Bintangs by night — blasting your mind with novel experiences.

Looking back, it’s impressive how insistent I was on chasing stoke and living life on my own terms. During the summer of 2021, I spent a week in Alaska with three friends. The four of us shared a camper van with two people on the thin mattress topper, one on the floor, and the last guy in a tent pitched on the roof. We backpacked in Denali National Park and none of us had actual backpacking backpacks. We each had normal backpacks bursting at the seams, with bulky sleeping bags dangling from the back.

I’m currently at the Stanford library, having settled into a more routine life. It’s the first time in a while that “routine” has a positive connotation. I’ve happily signed a lease, moved to the suburbs, and haven’t felt the itch to travel since we moved here. I’m also nursing a strained back, a function of not stretching and pushing too hard physically, but perhaps the physical pain reminds me that I no longer have Young Person Energy.

Young Person Energy

Young Person Energy (YPE) is what comes after puberty. As teenagers, we went through rapid physiological changes like acne, changing voices, and growing bodies. YPE isn’t as noticeable because it’s less of a physical transformation and more of an internal drive. Before we got co-opted into corporate life and sedentary lifestyles, we all had this pull that made us want to travel the world, talk to strangers, and climb trees.

YPE is the craving for adventure, and, most importantly, the willingness to put up with the discomfort, late nights, and wildness of it all. Some people preserve it. For most of us, whether it’s work’s stranglehold or the process of starting a family, our YPE gradually declines.

The people I admire most lived full adventures and then gracefully shifted into parenthood, while still doing cool shit. Doing both requires rapidly shifting identities. There’s nothing really stopping you from going all out on adventures until you become a parent, unless your desires shift first. From adventure-seeking honeybadger with YPE flowing through your veins to being completely content with stability.

The window where YPE peaks may never come again with such perfect conditions for adventure and novelty. It will become much harder later on, requiring higher activation energy, or you simply won’t want that type of life anymore.

I’m writing this because I feel nostalgic for that window in my own life. I’m almost certain it’s not coming back in the same form. But I’m still finding ways to keep YPE alive, like instead of spontaneous month-long adventures, I’m going on shorter trips that still pack the same punch. Through this perspective of someone just barely on the other side of peak YPE, I hope you’ll understand how precious this time window truly is while you’re in it.

My YPE Experience

I know this window is precious because I’ve seen what happens when it closes. You see, I coach people both younger and older than me. The younger ones wrestle with the same questions about life and work that I faced. But the older ones? They’re facing those exact same questions, but with more financial resources, more ingrained patterns, less willingness to try new things, and greater responsibilities. Years of prioritizing money, achievement, and status over adventure, connection, and purpose build up into a kind of sludge that’s hard to wash off. The contrast is stark. In almost all cases, the mid-life crisis hits much harder than the quarter-life crisis.

That’s why I’m grateful that when I was in my window, I made the conscious decision to put life first and job second. In 2020, through getting laid off from Uber with just ten months of work experience, I learned the tough but effective lesson of figuring out what actually matters.

Within weeks of starting the new job, I’d already organized a road trip to Park City with friends. It was August 2020, no lease, my first time living with people other than family since the pandemic. On our last night, we cooked a feast of steak, shrimp, sides, and desserts, sharing it all across a long wooden table. Then I drove to Denver for a two-week National Park road trip with my friend Jon. We’d do our jobs, drive a few hours, and squeeze in a hike, all before sunset.

I still remember our day trip to hike Mt. Huron, one of Colorado’s 14ers. With six dudes in one car, one guy voluntarily laid in the trunk of my SUV while cradling a leftover burrito from the night before. The last ten miles to the trailhead were unpaved gravel and you could hear him groaning in the back as we drove into ditches and over rocks. It was late October, and summiting 14ers was already not advised due to potential snowstorms. Two guys stubbornly wore shorts, like the boyish stubbornness I had in third grade when I would wait for the bus in basketball shorts while it snowed. We’d gone out to bars the night before, and that probably played a role in a couple guys throwing up around the 13,000’ mark. On the way down it got dark and we hiked the last couple miles completely in the dark. When we got back to the car, we all screamed with joy — safe, satisfied, and exhausted with joy.

That winter I organized a monthlong Airbnb in Frisco, Colorado, surrounded by dozens of ski resorts. At first, I practiced restraint and worked the standard 9-5, but the fresh powder was too tempting. Through some sneaky experiments, I learned that if I skied mornings from 9am-noon, I could still make it back with plenty of time to shower and scarf down lunch while beginning the work day. The mountain was quiet; all the other skiers were predominantly rich, old white dudes that seemed to have had successful careers and still knew how to have fun. I had tasted luxury without having the money yet and I couldn’t forget what it felt like.

Despite all the adventures and deliberately skipping work in the mornings, I was still putting in a ton of effort at work. I’d often work until 8 or 9pm and mentally I was still committed to doing a good job. Fast forward a few months and I got promoted to Senior Product Manager with less than two years of full-time experience. The job supported my adventures and the adventures fueled my work. Whether intentional or not, I made some big tradeoffs, like living without a lease, owning very little possessions, and basically not dating at all — only in hindsight were those all worth it.

From there, I continued to anchor my winters around skiing, choosing adventure over stability. Without the responsibilities or the sludge that comes with a mortgage, I could keep living as someone who hadn’t learned to say no possibility, with the benefits of location freedom and a solid paycheck. The annual ritual of migrating to mountain towns reinforced that life comes before work. I started to see how I could transform my life if I defiantly questioned the norm and curiously stepped into the realm of possibilities.

From 2021 to just a few months ago, I lived between Hawaii, NYC, ski towns, and the Bay Area where my family lives. Being in Hawaii continued to show me bite-sized glimpses of alternate realities. I got into surfing and yoga, and made new friends that didn’t ask me “What do you do for work?” as the first question. As I lived seasonally between tropical islands, snowy mountains, and tall skyscrapers, the stark contrast between each place helped me triangulate on what I wanted my days to look like. Over time, I noticed the growing desire for more stability and the waning youthful energy to always be adventuring.

That leads me to where I am today. In some ways, perhaps because of the recent shift to living permanently in Palo Alto, I feel like a grandpa. I like sleeping in the same bed every night and having the same morning routine. Instead of setting my alarm for 5:30am and mainlining caffeine before surfing at sunrise, I walk around the park and read books. I used to cram my days back-to-back with activities. I’m still getting used to having free time on a random weekday and not having the urge to fill it with some activity.

Grandpa Advice

Part of feeling like a grandpa at 28 is this impulse to share what I’ve learned. Not because I know something that others don’t, but because I’m still close enough to remember it vividly, yet far enough away to notice what I couldn’t see when I was in it.

I want to understand why the time window when YPE is at its peak is so precious.

To start, having YPE allows you to go on Big Adventures. These aren’t just ambitious goals. Running a marathon is ambitious, but the entire playbook is documented online. Starting a startup is ambitious, but if you’re doing it for the status — you’re missing the point. A Big Adventure has three key components: it’s ambitious, has no guaranteed outcome, and most importantly, you’re doing it for your own fulfillment. I’m talking about hiking the PCT, living in South America for months, biking across the country. You can’t analyze the ROI of these trips on a spreadsheet or ask ChatGPT to tell you if it’s worth it. These are experiences that are the antidote to watching short videos of other people telling you to buy random shit you don’t actually need.

Memory Dividends are what you get from Big Adventures, and rarely are they priced correctly. I still remember the feeling of accomplishment when we finally summited snowy Mt. Huron. Grilling salmon at a random park at 11pm as the sun was just starting to set in Alaska. Sandboarding down the dunes of the Sahara. These aren’t just fun stories I tell at parties. They’re memories accompanied by visuals, feelings, and energy that I can tap into and relive when my mind is particularly quiet. They’ve become reference points when I’m making hard decisions and reminders of what it feels like when I choose curiosity over comfort.

The thing is, you can’t properly value Memory Dividends until after the fact. When I was 25, I couldn’t have known how much that random Alaska trip would matter to me now. I wasn’t thinking about reliving potential memories in the distant future or how it would shape who I became.

Which brings me to Regret Asymmetry. I used to worry about falling behind in my career or not saving enough money. But then I realized: those things are all still available to me. I can focus on career next year. I can save more money in my thirties. But I can’t go back and be 24 with no lease and unlimited energy. That window closed already.

I’ve never met someone who regretted the adventures they took. Sure, hindsight is 20/20, but that doesn’t mean we can’t apply it to our lives right now.

So if you’re in your YPE window right now, take it from someone who lived without holding back and only recently slowed down. The safe, often more lucrative choices will always be there. The weird, wild, serendipitous ones won’t. Your present self will promise a better time later, a “someday” when the decision looks good on paper. That day does not come. I’ve watched friends with bigger titles and bigger paychecks miss it. I would still choose the same path.

And if you think you’re past the window like me? I’m actually learning that YPE doesn’t actually die or disappear. It just gets buried under routines, comfort, and responsibility. I can still feel it sometimes, like when my friends and I are planning something unnecessarily fun, or when I’m able to recreate a miniature version of YPE on the basketball court or on the jiu jitsu mat.

I keep thinking about those rich old dudes skiing powder on weekday mornings back in Frisco. They weren’t trying to be young forever. They’d built successful careers but refused to let those careers build them into someone who forgets what powder days feel like. They learned to carry YPE alongside the rest of life’s demands.

Because YPE isn’t about age or having no lease or unlimited energy. It’s about protecting that part of you that knows some experiences can’t be justified with reasoning. The part that wakes up at 4:30am to catch first chair at Tahoe, even when you have every reason to sleep in.

Maybe writing this whole essay has been my way of reminding myself not to let go of it. Not to stay young forever, but to remember what it felt like to trust curiosity more than comfort. To keep finding ways back to that feeling, even from my grandpa life in Palo Alto.

The window of peak YPE might close. But it’s still there, waiting for us to tap into. We just need the creativity to access it, the courage to choose it, and the desire to chase it.

P.S. I’m a coach.
I help ambitious people reconnect with their YPE. If that sounds interesting to you, learn more here.

We've been conditioned this way. School trains us to chase grades; employers rally us around quarterly targets. This doctrine might serve administrators and CEOs, but it doesn't serve us. Both spiritual traditions and sports coaches point toward the same remedy: release your attachment to outcomes. Focus on the practice, let the score take care of itself. But letting go feels disorienting. Without a finish line, what happens to our drive? Our ambition? Our grit? Do we just stop trying?

In my experience, the opposite happens. By shifting our attention to the process, we suffer less and, surprisingly, often get better results.

Ancient Wisdom for Modern Times

This message has been hammered home by ancient wisdom, but easily forgotten in modern times. Now we chase outcomes not just for satisfaction, but as social currency in a world where nobody sees the work itself.

You have the right to work, but never to the fruit of your work. You should never engage in action for the sake of reward, nor should you long for inaction.
- Bhagavad Gita

This feels counterintuitive because we’ve been taught to live for the rewards. Strive for A’s in school and promotions in work. Why should we work if we can't enjoy the fruits? In modern corporate contexts, this is a real dilemma, often requiring us to reimagine work entirely, in the form of entrepreneurship or a portfolio approach1.

A similar lesson emerges from Taoism around leadership:

The best leaders value silence and speak little. When the work is done, the people all say, ‘We did it ourselves.’
- Tao Te Ching

For a leader to serve without needing praise, the work itself must be satisfying. When you can't even claim the accomplishment, it better be worth doing for its own sake.

Both traditions point to the same truth: do the work, then disappear at harvest.

The Trap of Outcomes

I’m no stranger to suffering from outcomes… and likely neither are you.

When I was a product manager, the date of my promotion review was seared into my mind. In the months leading up, I’d show up to work with effort, but only because I believed the promotion would unlock the next tier of happiness. When the promotion felt less likely, I’d resent my work and coworkers, even though nothing had actually changed. When I did get promoted, less than two years into my career, I felt relief, not joy. I thought getting promoted would make me happier, but it just relieved me of further resentment.

This pattern shows up even at the pinnacle of achievement. After winning his first NBA championship, Kevin Durant said: “After winning that championship … I learned that much hadn’t changed. I thought it would fill a certain [void]. It didn’t.”

When conventional success doesn’t always hit like it used to, we often turn to the hedonic treadmill, redirecting income that should feel meaningful towards buying stuff to fill the emptiness. Or we move the goalposts, telling ourselves some version of “If this promotion didn’t bring me eternal peace, well then maybe the next one will.”

The mechanism of suffering has a distinct pattern to it - of shifting the measurement to future outcomes instead of attuning to the present. The deeper explanation can be attributed to uncertainty and fear. It’s scary to not have a set objective or specific timeline. When we’re used to getting what we want through mustering up tons of willpower and ambition, it’s disorienting to realize that we’re not in full control over the outcomes we care about.

But does the suffering come from missing the mark, or from the grasping itself?

If it's the latter, then being process-oriented is how we reduce suffering while continuing to work hard and make an impact.

What Process Looks Like

Shifting from outcomes to process is itself a process. After relying on goals and timelines for much of our lives, trying a different way feels daunting. But embracing process doesn't mean abandoning goals entirely. Dr. Srikumar Rao2, equal parts spiritual teacher and MBA professor, offers this guidance:

Set a goal, and the reason you set a goal is it establishes direction. Once the direction has been established, forget about the goal and put all of your emotional energies into the activities which will help you reach your goal… When you detach from the outcome, the probability that you will actually achieve the outcome you wanted increases dramatically.

The hardest part about all this is forgetting about the goal. We often set it, then check our progress against it daily.

To learn how to let go, we can study artists and athletes. Writers understand that writer's block isn't about lacking words, but being overly attached to what the words should be. The cure isn't trying harder. It's in lowering the stakes and sitting down to actually write.

I saw this mindset firsthand during my internship at Under Armour. Over a third of the 100+ interns were D1 college athletes. At the company gym, they worked out differently than the rest of us. It wasn't that they lifted more weight. I had been lifting for years and could match most of them (except the football players). But there was this dialed-in way they carried themselves that was subtle at first.

When they warmed up, they were repeating the same routines they had done thousands of times, but they weren't just going through the motions. I could see it in their faces. The present-moment noticing of how sore they were that day and what adjustments they needed to make. They had cultivated a level of self-awareness from years of training that let them notice tiny differences in their body and mind.

They took shorter rest periods than I did and moved with greater intensity. Most of the time, they were in the gym for less time than me. They showed up, warmed up deliberately with that embodied awareness, did their workout, and left. They knew there were many days of training ahead, and plenty of other things to take care of.

Now, when I visualize that black and red turf in Baltimore with the garage doors swinging open to the harbor, I remember how those fellow interns trained. It makes me wonder: how can I embody that same level of intentionality, focus, and awareness to process in my daily life?

Experimenting with Process

The "trust the process" message gets preached constantly and yet we still get caught in expectations and results. The natural drift of our minds is toward outcomes. Being process-driven isn't difficult - it's often about letting go and allowing ease, but it's also not obvious how to get started.

The British cycling team under Dave Brailsford became famous for their "aggregation of marginal gains," finding tiny improvements everywhere from bike seats to pillowcases to team bus temperatures. But cycling is highly quantifiable, with clear winners and measurable metrics. To apply this in life, you need to try many small things and actually notice if they create shifts. By default, we don't pay attention to subtle changes and what might be shifting as a result.

Being process-oriented requires diligence and meticulous focus. You'll need to practice microscopic examination like legendary basketball coach John Wooden who taught players how to put on socks and tie their shoes properly. This type of noticing can feel trivial and silly.

My recent examples:

• I noticed coffee tastes better from ceramic mugs than metal-lined travel mugs.

• Writing flows better when I’m sitting cross-legged on the couch. Coaching feels more grounded at my desk.

• Putting away dishes and vacuuming helps my mind wander in between deep work sessions. But other chores still feel like chores.

• I've always identified as an introvert, but this label created misconceptions. I get energy from others, but in particular ways. Parties with strangers drain me, but I love parallel presence: working in coffee shops, walking past neighbors with dogs, being around others absorbed in their own work. This led to concrete changes like paying for Stanford library access to work amongst students instead of working from home. But I also needed real connection too, so I swapped solo gym sessions with AirPods for jiu jitsu and basketball. These force me to be tech-free and fully engaged. The combination of quiet coexistence and active connection has noticeably improved my wellbeing.

Reflecting on Process

As Dr. Rao said, the goal sets direction, but staying focused on it means constantly measuring yourself against the distance remaining. Sometimes it's not even possible to know how close you are to your goal, which can feel just as bad as being far away. What helps you keep going is noticing tiny changes day after day.

This requires frequent reflection. You might already do annual or monthly reviews, but living in process means becoming attuned to the day rather than the year.

Daily reflection enables swift direction changes and cultivates granular attention. Instead of "This month was great because X and Y happened." it becomes "Today went well. I like sitting at this new spot at the cafe and I think reading before bed instead of scrolling on my phone results in my eyes feeling less strained in the morning, so I'll try this again tomorrow." It gets specific and nuanced. If you overthink it and try to force an insight to appear, it won’t work. Just notice and trust the process.

When you pay attention to the goal, you can't pay attention to other things, like new forms of growth or unexpected meaningful experiences3. The first time something unexpectedly nice happens, it's easy to dismiss it as trivial because it wasn't planned. But these anomalies compound and unfold into the real substance of a life well-lived. It manifests in the unexpected conversation that changes your perspective, the side project that becomes your calling, the random ritual you tried on a whim that now anchors you every morning.

Goals can provide direction, but don't let a known goal get in the way of unexpected good stuff.

Allow surprise to permeate.

Reversing the Scoreboard

Shifting to process doesn't mean letting go of ambition or effort.

I had a coaching client recently who was oscillating between total surrender and relentless pushing. He talked about being "totally okay with whatever happened," but something was off. He was surrendering to both outcomes and inputs, basically giving up. It reminded me of playing sports as a little boy. When things got hard, someone would just quit. But you can't quit. Even if you let go of the goal, you have to hold onto the process.

Surrender and wu wei don't mean doing nothing. They mean being process-oriented, not relinquishing everything.

You can work hard and be ambitious without fixating on external goals. "Getting shit done" is actually an awesome way to live, as long as you're getting shit done that you care about, where "done" means completed actions rather than achieved outcomes.

Instead of tallying outcomes like salary or wins, track process actions. For me, this means pursuing days well-lived: working on stuff I care about, taking care of my health, spending quality time with people.

If you're trying to lose weight, focus on meals and workouts rather than pounds lost. If you're a content creator, notice how you feel about a post before it goes live rather than obsessing over metrics. In my coaching work, I measure the value I create for clients regardless of what they pay, focusing on conversation quality over conversion rates.

When you stop keeping score, you start getting better at the game.

The Work Becomes The Win

Paradoxically, focusing on the process often leads to better outcomes. The athlete who competes for the love of the game ends up winning more games.

If you're not entitled to the fruits, as the Bhagavad Gita teaches, then the work itself must matter. This applies to everything: work, relationships, creative pursuits, even daily routines. Find activities where the joy is in the thinking, doing, and building - not the results, outcomes, or rewards.

Looking back at my past writing, I realize I've been circling this theme for years:

1. Embrace living in process rather than optimizing schedules

2. Find work with coherence between inner landscape and outer world

3. If you want to stick it out for the long run, discover your own sustainable ambition

4. Once you've found a groove, trust it. Live one good day after another.

Find work, relationships, and pursuits that are worth engaging in even without the promise of reward. When the work itself becomes satisfying enough that you'd do it regardless of the outcome, you've found something worth dedicating to.

That's when you can truly disappear at the harvest.

P.S. I’m a coach.
I help ambitious people shift from being outcome-fixated to process-oriented. If that sounds interesting to you, learn more here.

(Also, I updated my website! Lemme know what ya think.)

We live in an "always on", hyper-stimulated society. Brainrot and doomscrolling are now a part of our everyday vocabulary. Our minds are fraying, yet we’ve only just started to respond. As a society, our attempts to reclaim our time and attention have been mostly bandaid efforts. These ineffective workarounds assume the status quo, rather than envision bolder, healthier alternatives. Today’s technology requires us to mortgage our attention through notifications, ads, algorithms, and clickbait. But what if it didn’t have to be that way?

I set out to explore the following inquiry: What would it look like if Americans had a healthy, human-centered relationship with technology?

Tech Bandaids Aren’t Enough

There’s never been an era where we have spent so much time staring at screens. Remote work may have peaked during the pandemic, but the digitization of work is a bigger trend. Even hands-on work like healthcare and architecture now happens largely through screens. As more people spend more time behind screens, blurring the boundary between work and non-work, it becomes natural to drift into an 'always-on' state.

In response to the symptoms caused by the frictionless, engagement-maximizing design of smartphones and laptops, new products and businesses have been created to add constraints. An Amazon search for “phone lock box” yields over 2,000 results. A company like Brick sells a 3D-printed plastic cube with an NFC chip inside that blocks apps. They charge $59 for it, and although their sales aren’t public, they have nearly 100,000 Instagram followers, indicating desperation. Big Tech seems to be taking notice. Apple has introduced features like Focus Mode, Screen Time, and App Limits. But these are just bandaids.

The most effective action is to simply delete the apps and deactivate accounts, but that feels like a nuclear option. Although I care very little about keeping my Instagram followers updated with my life and likes no longer have so much weight on me, I still like to know what people are up to and sometimes I use the app to message people. I feel similarly for LinkedIn and X, I enjoy and get value from these platforms, but I also get sucked in easily, waste time, and often see content that I don’t care for or find nourishing.

So I’ve kept experimenting, trying to find a sustainable middle ground. I’ve used Brick, deleted apps, switched to black-and-white mode to dull the visuals, and even installed a Chrome extension that blocks all feeds. What seems to work best is staying signed out of all of these platforms and only logging in when I have something specific to post or check, but even then, it’s so easy to get sucked in. I tell myself that I’m redownloading Instagram just to share photos from a recent backpacking trip and 20 minutes later I’m lost in Reels.

It seems like we’ve been given two bad options: perma-delete and reclaim our attention, or try to use tech intentionally, but eventually cave.

Principles for Healthy, Humane Tech

If we were given the opportunity to reset the playing field and reimagine a healthier tech landscape, then it would start from reflecting on what we truly want as users. Crucially, we would want to think through these design principles and desired outcomes from a mindful, well-resourced place, rather than while we’re mid-doomscroll. In the following section, I outline some principles for designing tech products that I would want myself, as I seek to cultivate a healthier relationship with technology.

Minimum Viable Medium (MVM)

Short-form video might be the most "engaging" format, but engaging isn't the same as meaningful. As a consumer, I don't want to spend most of my time there. A healthier principle is what I call Minimum Viable Medium: match the fidelity of the medium to the importance of the relationship.

Different mediums serve different purposes. Text, image, voice, and video each come with varying levels of information and stimulation. Text is efficient but flat. Images add context, and voice carries emotion. Video demands everything: our eyes, ears, and full attention.

Dunbar's number tells us we can only maintain about 150 meaningful relationships, with our innermost circle containing just five people. We also know that we all have a finite amount of attention, not how long we can focus, but how much we can process. There's only so much we can process in a day before we're depleted.

Given these constraints, we ought to allocate our tech usage according to the importance of our relationships. Yet we do the opposite. We text our best friend across the country, compressing years of friendship into brief responses, then stare at TikTok videos from strangers for hours. Talking to a friend over the phone conveys so much more than texting back and forth, yet when was the last time we actually spontaneously called? Meanwhile, the predominant medium of short form video rarely conveys any depth or meaning. It's so easy to forget what you saw five videos ago.

The perversion goes deeper. We're literally giving money to influencers on the internet who don't know we exist, while our real relationships subsist on emoji reactions. We have shallow relationships with the people who matter most, and parasocial relationships with people who don't know our names.

In a society with healthy tech usage, people would match the fidelity of the medium to the importance of the relationship. Your inner five people would get voice notes and video calls. Your close friends would hear your actual laugh, not just "lmao." That acquaintance from work? A text is fine. Random strangers on the internet? It's not healthy to watch rapid-fire videos of irrelevant people. If there's no personal connection at all, text would be better. As content becomes more relevant to you, maybe it could gradually increase in fidelity. A blog you've followed for years might earn the occasional video, but not every random account deserves your full sensory attention.

With AI, this kind of intelligent filtering is increasingly possible. I could send a voice note that you receive as text if you're in a meeting, or vice versa. We have the tools to deepen real connections while filtering out the noise. The question is whether we'll use technology to strengthen the relationships that matter, or continue letting it scatter our attention across thousands of strangers who will never know our names.

Separation of Work and Personal

In the past, boundaries were built into the tools themselves. You left the desktop computer at the office. You dropped the briefcase by the door before heading out for date night. Now, the office follows us everywhere. Even if you mute notifications, the cultural pressure to respond or the sheer habit of checking keeps the lines blurred.

Our tools have become too multipurpose, trying to be everything to everyone at all times. The same screen that shows us our child’s photo also delivers quarterly reports. The same notification sound that announces a friend’s message also heralds a client’s urgent request.

The real opportunity is to design technology that respects context. For example, a personal mode that doesn’t just silence work apps but makes them vanish, so there’s no temptation to check in. Imagine time-based profiles that automatically shift your phone’s interface, with different wallpaper, app arrangements, and notification permissions depending on whether it is Tuesday at 2 PM or Saturday at 2 PM. The same principle applies in reverse. During the workday, I want to configure apps like Instagram to be inaccessible so that it’s easier for me to focus.

Separation matters because it lets us be fully where we are. To end the work day without the subtle tug to check email and Slack one last time before going to bed. To focus deeply on work without the impulse to check Instagram. Our tools should make these boundaries possible instead of eroding them. Of course, there’s an argument about willpower and just trying harder to resist temptation, but shouldn't we have tech options that align with our long-term well-being rather than tempting us in directions we have to fight against?

Single Purpose Tools

For most of human history, we did not live tethered to an always-on, attention-demanding machine. Today, many of us are intertwined with not just one but two devices: the phone and the laptop. They’re often the first things we touch in the morning and the last things we check before bed.

It’s remarkable that so many functions have been bundled into just two devices. The first iPhone felt magical, with a camera, flashlight, calculator, and calendar all contained in one. But has the pendulum swung too far? These days, I find myself dodging my own phone. In the morning I half-squint at the screen, trying to open my meditation app without catching the unread texts that pull me into someone else’s urgency. At the gym, I set an app blocker for an hour so I won’t get sucked into consuming content between sets. I want music while I lift, but that’s all I need it for. Sometimes I stash my bag in one place just so I can roam from machine to machine with my AirPods still connected, keeping the phone out of reach.

Technology works best when it feels like a tool we’re in control of, not one we have to wrestle or run away from. We use forks for some foods and spoons for others. We have dull knives to spread jam and sharp knives to cut watermelon. Each tool serves a specific purpose. The way we use our devices today is closer to running around with an oversized sharp knife for every task.

The rise of band-aid solutions like app blockers and phone lockboxes shows how much people crave tools that are less multipurpose and more intentional. I’m not saying we should go back to carrying a flashlight, calculator, and MP3 player in our pockets, but that we should be thoughtful about what to unbundle next. We already have the Kindle for books and Whoop for recovery. What use case might be next? Maybe an audio-first device that handles both guided meditations in the morning and workout playlists at the gym, so I can stay away from notifications and distractions during vital moments of the day. Or a lightweight navigation device that’s built for biking and hiking outdoors that guides me while allowing me to actually “unplug”. These kinds of purpose-built tools wouldn’t replace the smartphone, but they would make it easier to stay present and allow us to engage with unread texts and email when we actually choose to.

Embodied User Experience

Cigarettes needed warning labels and gruesome images addictive design overwhelmed individual willpower. Juul’s design slipped into high schools because its sleek design made it easy to hide, until it was effectively banned. Tech isn’t a drug, but the lesson still applies: when products are addictive by design, it’s unrealistic to expect individual restraint to carry the weight.

A healthier path is to build devices that move with our natural rhythms and respond to our self-directed goals. What if there was a phone that recognizes when you’ve been staring at the screen for thirty minutes and slowly darkens into a vignette until you put it down. Or a device that shifts with your circadian cycles, nudging you toward rest instead of keeping you wired late into the night. Even subtle embodied cues could help: a phone that vibrates in a steady heartbeat rhythm to remind you to pause, or one that slows its responsiveness when it senses fatigue. These cues make health tangible instead of leaving it up to constant self-management.

Technology should serve us, not sedate us. When I open YouTube or Instagram, I might genuinely want to see that first video or post. But by the fifth autoplayed clip, it’s no longer clear whether I’m choosing or being carried along. The line between agency and sedation is thin, and the current defaults are designed to keep us maximally engaged and minimally aware.

We were promised seamless personalization that adapts to our needs, but instead all we got was hyper-targeted ads. I can drag icons around my phone or bury the addictive apps a few pages back, but that’s trivial compared to what’s possible. Our devices know us in staggering detail, yet the only real personalization use cases are in advertising and eCommerce. What if that same intelligence was redirected toward our health, focus, and flourishing?

It would be great I could set an objective for myself, whether it is the number of pickups per day, the total hours of screen time, or how focused I want to feel. My phone should help me design a plan to reach that goal. It could show me where I am spending the most time and then take action: blocking certain apps during work hours, dimming the screen at night, or inserting pauses when I have scrolled too long. LLMs make this level of personalization more feasible than ever. The same algorithms that predict what will capture our attention could just as easily support what we choose for ourselves.

The point isn’t just to take breaks. Watching TikTok for ten hours with pauses in between doesn’t move the needle. Health-first design would help us actually downshift, aligning technology with natural cycles of rest and activation, and preventing us from flooding our nervous systems with constant stimulation. If we can’t always use our devices mindfully, then our devices should help us be more mindful.

We deserve the ability to customize our devices at a deeper level, not just rearranging icons but shaping the very defaults that guide how we relate to them. Right now, the richest person in the world and someone working paycheck to paycheck both use the same basic phone. This is an incredible equalizer, but it also leaves a lot of possibility on the table. If we can dream bigger, our devices can become real copilots in the lives we want to create, rather than constant tests of our willpower.

Aligned Incentives

Of all the principles for healthy, humane tech, this might be the most important and the most challenging to implement. Today's fundamental problem is simple: the incentives between tech companies and individual humans are misaligned. Instagram makes more money when I spend more time on the app, but maximizing my time there isn't what I want, even if my doomscrolling behavior suggests otherwise. If you asked me in a mindful, well-resourced moment, I'd tell you I only want to see content from people I actually follow, and even then, only posts that are interesting and relevant to me.

We're already seeing the emergence of attention inequality. Netflix and YouTube offer paid tiers without ads. Spotify Premium removes interruptions. Wealthy families buy their kids Light Phones and send them to screen-free schools, while everyone else gets the full force of the attention economy. We're creating two classes: wealthy kids with healthy nervous systems and normal focus abilities, and poor kids with ADHD. It’s Black Mirror vibes and it’s already happening.

The path forward requires business models where companies become accountable to us as customers rather than to advertisers buying our attention. When we pay for something directly, the incentives shift. Substack and Patreon already demonstrate how creators and consumers can connect without engagement metrics driving the relationship.

But we need more radical changes. At minimum, we should control our own algorithms. Imagine choosing between an algorithmic feed and a chronological feed of just the people you follow. Better yet, what if you could fine-tune your own algorithm? "Show me 80% content from people I know, 20% discovery." or "Prioritize text over video." Right now, these algorithms are black boxes designed to maximize watch time.

The deeper issue isn't just ads or algorithms in isolation. It's that we're consuming too much content overall, and it's from junk food sources. We're drowning in high-fidelity videos from strangers instead of simple messages from friends. Even if I could perfectly control my algorithm, if I'm still watching three hours of content from people I don't know, the problem persists.

This shift requires us to fundamentally reorient what we're paying for. When I see content I didn't ask for from accounts I don't follow, it's functionally identical to seeing an ad; it's an unwanted intrusion on my attention. The true cost of "free" platforms isn't just the ads themselves but the entire architecture of distraction they create. Until we make this cost visible and start pricing it accordingly, we'll remain stuck in a system where our attention is the product being sold, and our wellbeing is collateral damage.

A More Human Future

When I dream of a different life with technology, I see myself waking to gentle light, not my phone's nuclear warning sound. I meditate without devices, or maybe use an audio device built specifically for listening, not scrolling. During the day, my phone hides distractions behind real friction. A truly smart smartphone would triage messages: my mom or girlfriend's calls come through immediately, but my friend's meme can wait until 5pm. Work apps stay in work mode from 9 to 5, then disappear. I’ve never wished I could access Slack at 2pm on a Saturday.

This future feels within reach. LLMs are making software cheaper to build, and the opportunity to build healthier social applications is more accessible than ever. What matters most is recognizing that we already have the means to be more ambitious with our relationship to technology. We don't have to wait for the stars to align before building better.

We've normalized "brainrot" and "doomscrolling," but what if we cultivated brain bloom instead? The productivity world talks about building a "second brain," but that barely scratches what's possible. Brain bloom isn't about storing more information or being more productive. It's about technology that prioritizes healthy nervous systems over constant stimulation. It's about fostering real connection between humans instead of parasocial relationships with strangers. It's about enhancing what makes us uniquely human: our ability to imagine, sense, create, and be present with each other.

Right now, our devices are making us less human: more distracted, more isolated, more anxious. But technology also has the potential to make us more human: more present, more connected, more ourselves. The tools and knowledge exist today. The choice is ours.

P.S. I’m a coach.
I help ambitious people find work that matters, design their version of the good life, and foster a healthy relationship with technology. If that sounds interesting to you, learn more here.

One is not better than the other. In my career, at times I’ve felt more like a missionary, drinking the kool-aid and excited to show up to work everyday because I genuinely thought what I was doing was saving the world. At other times, I’ve felt more like the mercenary, viewing the job as just a job, while appreciating the money for the lifestyle that it enabled. The interplay between these two modes shifted whenever I changed jobs, but it also morphed even when I was in the same role at the same company, showing how complex and dynamic this can be.

These two archetypes have shown up in different contexts beyond corporate work for hundreds of years. Missionaries were (and still are) devout religious people that travel the world spreading the word of God. Mercenaries have traditionally been the “hired guns” that fight in wars for money rather than political allegiance or patriotism.

The longtime advice from Silicon Valley legends1 has been to hire teams of missionaries, not teams of mercenaries. By employing people who deeply care about the mission and feel passionate about the problem, entrepreneurs will recruit people who are more engaged, motivated, and perhaps even work harder.

Today, I see the cracks beginning to form in this career strategy, for both employers and employees. It’s no longer tenable to promise meaning, empowerment, and glory to every one of your employees. Today's corporate 'missionaries' can dedicate years to a company's mission only to be laid off via email.

A century ago, Ernest Shackleton’s Antarctic expedition posted an ad that was brutally honest: “Men wanted for hazardous journey. Low wages, bitter cold, long hours of complete darkness. Safe return doubtful. Honour and recognition in event of success.” It’s hard to imagine, but back then there were people who signed up for this big adventure. Actually, I’d be willing to bet that many of us today are actually seeking something similar: a meaningful challenge that stretches and transforms us and requires total commitment and focus.

But it’s hard to find if we are only looking at full-time jobs to fulfill those expectations. Companies can only be successful to the extent that they solve customer problems and generate a profit consistently over the long run. Things don’t always go smoothly and as a result, downsizing, layoffs, and hiring freezes are all quite normal.

The trade is no longer fair. In the past, you could work at the same company for 40 years and along the way, start a family, buy a house, and then retire with a healthy pension waiting for you. Founders and CEOs, despite some being benevolent dictators, are not always going to have your back. They certainly can’t match the same level of power as kings and religious leaders. Devoting your life to a company is a fundamentally different thing than devoting your life to a kingdom or religion. Walk into any church, mosque, temple, or ashram, and you’ll likely be met with open arms and a bowl of warm food. That level of reciprocity is simply not the case when it comes to modern work, nor should it be.

After getting burned as a missionary, it’s tempting to swing the other way and treat work as nothing more than a paycheck. But it’s hard to sustain. Forty hours a week is too much of your life to fake indifference.

The missionaries I met through writing my climate tech newsletter moved with incredible conviction. To them, saving the planet was the most important thing, and that meant pouring everything into their work. But the mismatch between that passion and market realities (customer adoption, unit economics, fundraising cycles) often created an impossible tension. They'd keep giving and keep grinding until burnout became inevitable.

That's the cruel irony of being a missionary in corporate life. You're encouraged to treat the company like family, to bring your 'whole self to work,' to find your tribe. Then when layoffs come or the startup fails or you simply burn out, it feels like that family abandoned you. Whether you leave voluntarily or get pushed out, when you've given all of yourself to the job, the loss carries the heaviness of grief.

The mercenaries, mostly in finance or law, face a different void. At 18 and broke, money feels like the gateway to everything. At 27 and making $400K, they discover there's nothing more to buy2. It's one of the strangest phenomena I've witnessed: young, wealthy, unencumbered, yet spiritually bankrupt. They never spent time figuring out who they are or what they want, so the money just accumulates without purpose.

To be clear, I'm not against high-income careers. The VP at Google making $1M a year with three kids might feel deeply purposeful, even if primarily motivated by money. There's meaning in providing security, funding college, and creating opportunities for others. But without connection to something real, money stagnates. Money that doesn't flow, like water, turns rancid.

I've oscillated between missionary and mercenary myself, each swing bringing fresh disappointment. It’s not fair to expect all your sense of purpose and fulfillment to come from your one full-time job. It’s also a fool’s errand to think that there’s a specific number of dollars that will allow you to feel happy and at peace in perpetuity.

So where does this leave us? If the missionary path leads to burnout and betrayal, and the mercenary path leads to spiritual emptiness despite material abundance, what's left?

Rather than swing between two bad choices, I propose a third option: becoming a Free Agent.

The Free Agent recognizes what both missionaries and mercenaries miss. You can be sovereign without being solitary. They channel the passion of missionaries but refuse to martyrize themselves for companies that would post their job opening before their obituary. They practice the discipline of mercenaries: earning well, saving aggressively, negotiating fearlessly, but refuse to let money be the only scoreboard.

Like athletes between contracts, Free Agents understand they're always looking to join a team, to contribute to something meaningful. But they also know that trades happen, seasons end, and sometimes things just don't work out. This awareness is sobering clarity.

It's a double entendre that captures the whole philosophy. As a free agent, you're liberated from the scripts others have written for you. And you're agentic, capable of making choices and then actualizing them.

This isn't about wandering aimlessly between gigs. Free Agents do the upfront legwork of constructing what many call a portfolio career. What makes it a coherent patchwork isn't some neat story about how everything connects. It's coherent because each piece serves a specific purpose. They look inward to identify what they actually need from work: money, community, stability, learning, impact, creativity. Then they deliberately seek different elements that satisfy each requirement.

Free Agents take many forms. Some run agencies while exploring new ventures. Others keep full-time roles but pursue side projects, like producing films, hosting pop-up bakeries, and operating online pottery stores. Remote workers chase powder days or surf swells without asking for permission. Parents (presumably with more years of experience) leverage their seniority to expand mornings and evenings with their kids. The setup varies, but the principle remains: consciously designing work to serve your actual needs, rather than blindly oscillating between missionary and mercenary.

The Free Agents I know are ex-bankers, engineers, and consultants reimagining their relationship with work. They’re not throwing it all away. They’re experimenting with ways of working that feel creative, meaningful, and financially solid while remembering to lean on the skills they’ve worked hard to hone.

I've embraced this concept for myself, and it's given me both the freedom and the responsibility to figure out what work means to me, and how I want to relate to it. It's harder than just following a playbook, but it's also more honest and fulfilling.

After years of roleplaying missionary or mercenary, I feel more refreshed and energized with this Free Agent mindset. It’s given me permission to explore things that I wouldn’t have if I was solely optimizing for meaning or for money. I’m able to pursue my own work like my coaching or my writing, but I’m also able to explore working with others and teaming up to build something that is bigger than what any one individual could create on their own.

The shift from missionary or mercenary to Free Agent isn't a one-time decision. It's an ongoing practice of choosing sovereignty over scripts, integration over optimization. It starts with asking yourself: what do I actually need from work, and how might I construct that rather than hoping someone else will provide it?

This seems to be catching on. More people are rejecting the false binary and creating their own third way. At a time when people are starved for meaning yet balancing the practical demands of an ever-more unstable world, the Free Agent approach offers a path to honor both your need for purpose and your need for security, without sacrificing one for the other.

If this resonates with you, I'd love to hear about your own journey between these modes. I've been connecting with folks making the shift, and it's always exciting to hear how different people combine these elements of work.

P.S. I’m a coach.
I help people find work that actually matters and design their version of the good life (i.e. become Free Agents). If that sounds interesting to you, learn more here.

He describes the aftermath like this: “The right side of my brain literally shut down. So my level of empathy was pretty low, and the left side of my brain was a machine. It was like a supercomputer.” He became a “business Terminator”, still human, but emotionally disconnected, with analytical horsepower cranked to the max. During those years, he climbed the ranks at Aetna and eventually sold the company to CVS for $69 billion.

As I listened, I started to see his story as a metaphor for where we are right now with AI.

The Left/Right Brain Framework

The human brain can be thought of as split into two hemispheres. The left half is adept at language, logic, analysis, and reasoning. Its right counterpart handles creativity, emotions, embodiment, and contextual meaning. Author Iain McGilchrist describes the left hemisphere as “using narrow-beam attention to one detail after another, sees what is familiar, certain, static, explicit, abstract, decontextualized, disembodied, categorized, general in nature, and reduced to its parts.”

The right hemisphere is the exact opposite: “Bringing broad, open, sustained, vigilant attention to bear on the world, it sees what is fresh, unique, never fully known, never finally certain, but full of potential. It understands all that is, and must remain, implicit: humor, poetry, art, narrative, music, the sacred, indeed everything we love; it understands that nothing is ever static and unchanging, that everything is flowing and interconnected.”

Of course, both hemispheres are involved in almost everything. But McGilchrist’s framing is useful. In The Master and His Emissary, he describes the left brain as the emissary and the right as the master. The left works in parts and components; the right sees depth and the whole. His central point is critical to understand right now: the analytic power of the left should serve the integrated vision of the right, not the other way around.

Information Processing, Not Intelligence

I’m not trying to come off as a boomer Luddite who prefers to communicate via pigeon mail. I use AI tools every day. When it comes to writing code, parsing PDFs, or extracting insights from dense documents, LLMs are awesome.

However, I think we’re conflating information processing with true intelligence. It’s like sitting in a sauna at 190°F and convincing yourself you’re working out. You might be sweating, but you’re not getting any fitter. The same goes for AI. It moves fast and works efficiently, but that doesn’t mean it actually understands anything.

With tools like Suno, I can generate a song in a chosen genre with custom lyrics, but the result is a novelty to show friends, not something I’d add to my playlist. I can talk to ChatGPT about personal problems, but reasoning through anxiety with an LLM feels like running my thoughts through the wash with no detergent. Lots of motion, little cleansing.

My coaching clients notice the same. Using AI as a therapist feels innovative at first, but it doesn’t lead to meaningful transformation. And in companionship, the gap is even bigger. I value in-person presence far more than a call or FaceTime, and texting barely carries any emotional weight. We keep assuming LLMs can deliver embodied empathy and connection, when all they’re doing is processing inputs and predicting the next token.

AI as the Hyper-Left Hemisphere

Large language models reflect the same cognitive imbalance. They behave like hyperactive left brains by breaking wholes into parts, extracting patterns, and predicting what comes next without any sense of meaning.

The process begins with scraped internet text, stripped of context and lived experience. GPT-22 was trained on 40GB of Reddit posts and GPT-33 on 570GB from broader sources, but even at that scale, it’s still a map of abstractions, not the actual terrain of reality. That text is then split into tokens, disembodied fragments that the model learns to predict in sequence. The goal isn’t to understand. It’s to guess what comes next.

Then comes fine-tuning, where human experts label data, write evals, and reinforce preferred outputs. What wasn’t scraped during the internet sweep gets hunted down like rare loot, like Anthropic buying out-of-print books and then slicing pages up to feed to the models.

Not all information is documented online though. An indigenous healer’s tacit knowledge can’t be scraped and labeled. A professional athlete’s mastery is cumulated from thousands of hours of practice, coaching, and feedback. And someone like Rick Rubin seems to operate more off of vibes and taste than theory or technique. You could ask any of them how they do what they do, and you wouldn’t get a logical answer. Not because it’s not possible to learn, but because some forms of knowing aren’t transferable through indirect experience (or LLMs). And maybe that’s not a bad thing.

In deployment, the same constraints persist. LLMs rely on prompts and context windows, not situational awareness. They generate responses fluently and obediently, but never pause to resist or invite exploration. Whether it’s text, image, voice, or video, the interaction remains flattened. It’s still just high-speed information prediction severed from lived context.

Hemispheric Imbalance in Humans

Mark Bertolini’s 18-year ordeal as the “business Terminator” illustrates left-brain dominance: intensely detail-oriented while emotionally disconnected. He isn’t the only case.

Schizophrenics, thought to be in left-brain overdrive, perceive a fragmented world, often imagining people have turned into machines or zombies. Stroke victims with right-brain damage show a similar pattern, with flattened speech, monotone delivery, and a loss of irony, humor, metaphor, and emotion. With less embodied awareness, they end up forgetting their own limbs and miss social cues. As the left brain takes over, attention narrows into tunnel vision aperture, focusing only on what is explicit and graspable.

But right-brain dominance is just as limiting. Without the left brain’s language, logic, and control, people lose the ability to form coherent sentences even though they still understand tone, emotion, and metaphor. The right hemisphere processes richly and deeply, but without the left hemisphere’s capacity for expression and control, perception is rich while articulation and action remain stunted.

One hemisphere is not better than the other.

Humans (and the right hemisphere) as the Master

In the modern context, McGilchrist’s idea that the master must guide the emissary becomes a nested metaphor.

Originally, the right hemisphere, with its sense of the whole and its awareness, was meant to guide the left hemisphere, which specializes and works in parts. With AI, the parallel is clear: humans must guide the machine, not the other way around. Instead of being glued to technology like attention-sucking parasites, we should repurpose our relationship with AI more like an exoskeleton, a tool that multiplies our intentions and amplifies our power.

Seen this way, it makes sense why AI’s greatest value shows up in domains aligned with left-hemispheric strengths: programming, research, data analysis, and automation4. We already see products guiding programmers through nearly every step of development, as well as advances in drug discovery, where AI accelerates biology research, and in law, where it speeds up contract review. But why these areas? Is it simply that practitioners tend to be early adopters, or is it that the work itself is inherently suited to the strengths of LLMs? If it’s the latter, slow adoption elsewhere may reflect the natural limits of where AI has leverage.

A different perspective might help. In An Immense World, Ed Yong shows how every animal perceives reality through its own configuration of senses. A mantis shrimp, for example, has up to sixteen photoreceptor types compared to our three, which allows it to perceive 100–200 times more colors than we can. That range is not just invisible to us, it is inconceivable. We can’t even begin to fathom what it means to see colors outside the palette of human experience.

The same bias shows up with AI. What we call “superhuman” is always relative to human capacities. Because AI can generate words effortlessly, we mistake its fluency for depth, overlooking the resonance and sparks of novelty that emerge only through the slower, organic process of human writing.

The better analogy is a car. A car is not a genius because it outruns us on the highway. It is superhuman in one narrow sense: speed. AI is superhuman in information processing, but intelligence is more than pattern-matching or fluency. True general intelligence would require the right-brain capacities of context, empathy, embodied presence, and meaning-making—areas where AI consistently falters. In that sense, AGI as evocatively envisioned may not be possible. At best, we are building a savant emissary, not a master. The real leverage comes not from the raw horsepower of a model, but from the context and domain in which it is applied.

The top beneficiaries will be those who treat AI as the emissary, not the master. Those who recognize the irreplaceable qualities of human creativity and judgment and how to direct the machine’s horsepower will reap the rewards.

Creators will use AI to brainstorm and plan, researchers to accelerate discovery, and entrepreneurs to extend their productivity without large teams. In every case, the human sets the vision and directs the AI towards specific, discrete tasks.

Speculation is heated within the creative industries, but I don’t think movies will be replaced by entirely automated productions. Instead, AI will be folded into the workflow, taking on laborious tasks like storyboarding, special effects, or editing. Early Disney films required thousands of hand-drawn frames, until digital tools streamlined the process. The medium improved, but gradually, not through an overnight Cambrian explosion. I think AI will follow a similar path, enabling creators5 to focus more on vision and meaning while the machine carries the weight of execution.

The Path of Integration

Pre-AI, the world was already tilted toward left-brain thinking: optimization, fixation, endless measurement in the economy, policy, and culture. With the rise of what feels like “a country of geniuses in a data center,”6 it has never been more crucial to restore something more holistic and connected. That work begins at the individual level, as in each and every one of us.

You probably know someone (or are someone) who lives almost entirely in left-brain mode. The calendar is time-blocked and every minute is accounted for. Meals are tracked by macros and workouts are logged on Strava. Even something as simple as sleep is reduced to a single score. Relationships are managed through a personal CRM that reminds who to reach out to. Meditation is collapsed into a productivity tool. Every part of life becomes a system to optimize and a problem to solve. Life begins to resemble a factory. Hyper-efficient and structured, but hollow and bland.

Right-brain presence feels different. It relies more on energy level than amount of time available to make decisions. It’s when you lose track of time in conversation with a friend. It’s noticing the gut feeling that, if it had a voice, would say “I don’t know why, but this feels right” and trusting that. It’s when you pause mid-walk just to stare at a tree because something about it feels alive. It shows up as emotional awareness, connection to one’s body, creativity, imagination, and intuition. You can’t optimize your way into it. You have to feel your way there. Cultivating that presence isn’t just a luxury. It might be the only real antidote to the disembodied logic loop we’re building.

As technology advances, it becomes ever more vital to remember what it means to be human. As AI enters more of our livelihood, we need to cultivate embodiment, relationality, emotional awareness, and creativity with even greater care. The irony is that the very things that once looked like unproductive downtime, like playing outside, moving our bodies, and sitting in silence, are becoming essential if we want to feel human at all.

Most people assume adopting new technology simply means replacing the old. But we have to go further and ask what else must change if we want balance. The more I use AI, the more I value yoga, meditation, sports, and in-person hangouts. What once felt like optional hobbies, now feels necessary. For me, playing basketball with a bunch of dudes is a countermeasure against being sucked into a techno-void that looks like some AI-generated mishmash of WALL-E and Ready Player One. It’s how I preserve the human parts of me that machines will never be able to replicate.

Whatever your stance on AGI, the deeper point is that these mediums change us as users. Social media, smartphones, and now AI have nudged us toward disembodiment and over-fixation. Everyone is free to choose how to respond. I’m choosing to lead with the master, not the emissary.

Return of the Master

Mark Bertolini’s story fascinates me because not only does he recover from extreme left brain dominance to a more balanced way of being, he also happened to be quite financially successful both during the 18 years of one hour sleep a night and after his recovery.

In his “business Terminator” years he drove Aetna’s turnaround, producing a 652% shareholder return. Starting in 2015, he introduced yoga and mindfulness to the workplace, raised wages, paid down student loans, installed gyms and healthy food, and even rolled out pet therapy. In total, the company was investing 130 million dollars annually into employee well-being. Instead of profits plummeting, the opposite happened. Over his entire tenure, shares went from $9 to $208 before the business was sold to CVS for $69 billion.

Eastern practices became central to his life. On the podcast, I heard him mention yoga, Reiki, craniosacral therapy, and Samadhi - blissful concentration. He even has Soham, the Sanskrit phrase for “I am that,” tattooed across the back of his neck to remind himself that everything is one. Not exactly what you’d expect from an old white guy from Michigan who runs a multibillion health insurance company. Mark is part of a growing collective of heart-led business leaders proving that compassion and wholeness don’t have to be at odds with profits and growth.

The opportunity in front of us is to make the same shift as Mark, but at scale.

AI may free up time, but that doesn’t dictate how we’ll spend it. We can drown in shallow content and chase material distractions, or we can reorient toward presence, discernment, and deeper connection—with ourselves and each other.

McGilchrist reminds us that “Machines serve us well when they relieve us of drudgery, but human affairs must remain human.” He warns of the simulacrum, a hollow, unsatisfying veneer of life, a representation that resembles reality but leaves us empty. The danger isn’t that AI takes over, but that we forget what’s worth preserving. We pour our resources into making machines better. But rarely stop to ask what ‘better’ even means, or what we risk leaving behind.

As for myself, I’m paying closer attention to what feels natural. I’ve cut back on social media to reclaim my attention and remember what it’s like to feel grounded. Yoga, jiu jitsu, and pick-up basketball pull me out of my head and back into my body.

The choice is simple: use the machine like a tool, or let it use us. What I’m learning, and what I’m inviting you to consider, is that feeling fully alive doesn’t come from the sheen of social media or simulated conversation. It comes from presence, movement7, and connection. From doing real shit with real people.

P.S. I’m a coach.
I help ambitious people find work that actually matters and design their version of the good life. If that sounds interesting to you, learn more here.

Anecdotally, I feel better with zero FOMO. Maybe it’s because I’m in a season of contraction, trying to preserve energy and focus on fewer things. Or maybe the platforms have deteriorated so much, from friends-first to content sludge that my tolerance finally broke.

In lieu of not knowing if I’ll ever post on Instagram again, I want to make this month’s blog more fun and friendly. Fun isn’t always the obvious strategy, but it’s an interesting way to play with form and constraints. It comes up in coaching too. A client hits a fork in the road: grind it out or quit. But sometimes, the better move is to make it more fun. That shift can be just as effective. Instead of optimizing for popularity or profit, go for flow.

So in that spirit, here’s this month’s brain dump:

I moved to Palo Alto!

We moved here about two months ago, right before my girlfriend started residency at Stanford. For someone who’s spent the past few years living nomadically, always keeping the question of “What’s the best place for me to live?” in the back of my mind, it’s been surprisingly easeful to not only move somewhere I’d never test-lived, but also didn’t even choose.

Over the years, I’ve lived in San Francisco, New York City, Lake Tahoe, and Oahu. Back when I was moving into a new sublet every month, the thought of living in Palo Alto never crossed my mind. I associated it with the tech industry and extreme wealth. That’s not wrong, but there’s definitely more here than just stereotypes.

The first few weeks were rough. I didn’t know anyone and didn’t really put myself out there. It was the first time in a while I actually felt lonely. Gradually things started to shift. With each new piece of furniture, our apartment evolved from bare-walled box to slightly more home-y. I started to meet people through friends and also by joining new communities.

When we were ranking residency match preferences, I said I wanted San Francisco. It felt like a real city. More of my friends lived there. Palo Alto felt slightly suboptimal for just me, but clearly the best choice for the two of us. On one recent evening, something shifted. I left SF after a day trip, just as the late afternoon fog and chilliness set in. When I stepped off the CalTrain in Palo Alto, the air was warmer, it was golden hour, and the sunlight was gently streaming into my eyes. It was quiet and calm. Maybe it’s post-rationalization, a trick of the mind to make peace with where I’ve landed. But if so, it just shows how powerful our thoughts can be.

Two months in, and our apartment is still not completely furnished—and that’s totally fine. There’s still big pieces moving in my life, but I feel rooted here. This place already feels like home.

Getting into Jiu Jitsu

I’ve been training jiu jitsu for a few weeks now. I’d wanted to try it for years but kept putting it off. It never felt easy or straightforward to get into. That changed when I moved to Palo Alto and a new gym opened up across the street. Given how suburban and quiet this neighborhood is, it felt like a sign that I had to try.

The first session started off chill and then crescendoed into intense. By the end, my partner and I were full-on trying to choke each other out. I work out regularly, but it had been a long time since I’ve been fully drenched in sweat. Having an opponent is way more demanding than hitting sets of ten on a weight machine.

The next morning, I woke up feeling like I had gotten hit by a truck—but with a crystal clear mind. No tension, anxiety, or frustration. I’d originally wanted to try jiu jitsu for physical fitness, but the mental clarity was what convinced me to keep showing up. As a man and as a coach, I’m learning how vital it is to have healthy ways to express aggression and anger. This worked.

I’ve already noticed a few things. I’m relearning how to use my legs. Most of adult movement is walking, running, squatting. In jiu jitsu, I’m often on my back, using my legs as if they’re as dexterous as my arms, but way stronger. It’s weirdly familiar, like remembering something my body knew as a kid, but now in the context of trying to beat up another adult.

Jiu jitsu mimics the conditions I love in skiing and surfing. Your opponent shifts positions quickly, like a change in snow angle or wave speed. You can’t half-pay attention. It demands full presence. I’ve felt flow in deep work or good conversation, but with weightlifting, where I’m alone, wearing AirPods, checking my phone, it’s harder to access. Here, you leave your phone away. Someone’s trying to submit you and you have to pay attention.

It also fits with my broader health goal of improving my athleticism. A few years ago, I noticed the best skiers seemed more athletic than me, with greater flexibility, agility, endurance. Same with surfers. Jiu jitsu has that same emphasis on full-body control. Our warm-ups include cartwheels and somersaults. I can’t ski or surf every day, but I can walk across the street to jiu jitsu. For now, it’s become one of my main practices.

Playing in Lake Tahoe

I seem to go through cycles, periods of deep introspection followed by lighter, more playful stretches. Right now, I’m in the latter. Just playing, for the sake of it.

I recently took a two-day, one-night trip to Lake Tahoe. We crammed five of us into my car - less comfortable, but more fun. It reminded me of trips as a kid, when there was always something to talk about or look at.

The first day, we hiked a quiet trail with an epic view, snacked on a picnic blanket by the lake, and jumped in for a quick swim. For dinner, Geo brought marinated Korean short ribs in a cooler. We feasted: meat, kimchi, grilled mushrooms, a giant bowl of watermelon we picked up on the way. Afterward, we caught the sunset from a dock and played Skull King, a betting card game we all got so into that we set alarms for 7am just to squeeze in one more round before the next day’s activities.

On Sunday, we kayaked early while the lake was still calm, scouting for a rock or dock to jump off. We found one, covered in seagull poop. I jumped anyway. Then we swam and played Spikeball on the dry green grass by the beach. Probably one of the nicest textures for feet to be on.

I go to Tahoe a few times a year, and on the drive back I kept thinking about how easy it is to do things that usually seem reserved for rich people. Sure, it’d be nice to own a house or kayak, but those are just nice-to-haves. The real ingredients are the idea, the energy, the friends, and the willingness to make it happen. Of course money plays a role, but it’s rarely the main bottleneck to enjoying life and playing like a kid again.

Noticing what matters to me

With the move to Palo Alto and the shift from nomadic to rooted, I’m having new experiences that feel meaningful in a different way.

My girlfriend and I recently spent an afternoon with the 89-year-old woman we lived with for a month last year. We brought her flowers and snacks, she baked us cookies, and taught us how to play Farkle, a dice-based betting game. She still drives herself, does her own grocery shopping, and has a full calendar: book club on Tuesdays, cribbage on Fridays at the senior center. In a culture obsessed with youthful celebrities and ephemeral trends, time with elders always recalibrates me. I learn more than I expect, and it’s often more fun than I assume it’ll be.

Getting our couch turned into a surprisingly satisfying side quest. After weeks of indecision at Crate & Barrel, we almost bought a $3,000 green couch. Meanwhile, I spotted a different Crate & Barrel model on Facebook Marketplace for $1,000. It wasn’t symmetrical, so we passed, but then they dropped the price to $600. An hour later, we paid for it. I tried hauling it back solo and failed, then rented a U-Haul and lucked out because my friend Parker happened to be in town on a business trip. He helped me carry it up the stairs. That night, I cooked a feast for us to share. It felt like the good kind of trade: effort, coordination, and a meal with a friend at the end of it.

I’ve also been enjoying our new coffee table, bought from a family with a toddler who didn’t want to risk the glass. It has a clear top and storage underneath, so I can display photography books and magazines. I’ve been wondering why it feels so good to have. Maybe because it’s functional, expressive, and makes it easier to host. Before, there wasn’t even a surface for snacks or card games. It’s not just a table. It’s a sign that we’re settling in and doing it with intention.

On a recent Friday, I took a day trip to San Francisco. I met a friend building a startup for coffee, then had lunch with a former coaching client who’s now a friend, caught up with an online writing friend, and finally met someone from Twitter for the first time at Dolores Park. As we walked a couple laps around the park, he opened up about his startup struggles. The business was doing well, everything trending up and to the right, but he was thinking about leaving. As I listened, it became clear that the tension was with his cofounder.

The conversation turned into an impromptu coaching session. I guided and challenged him, helping him think through how to move forward in a way that was still ambitious, but also acknowledged his burnout. What mattered to me was that I was fully present, willing to coach with no agenda or financial incentive. I was just trying to help. Coaching started for me that way, with people reaching out organically. It’s good to see that even after building a business around it, I still feel like I’m doing it for the right reasons.

Riffing on Investing and Meaning

I’ve been wondering why alternative assets have gotten more popular over the years. It’s not just better access or looser regulations. People are bored, have money, and want to spend it in ways that feel good. In the digital age, having a sports car or diamond chain doesn’t carry the same weight it used to.

I think people are searching for ways to invest their money that feel meaningful. Especially if you don’t have a family yet, wealth can feel intangible when everything’s automated, from paycheck to Vanguard. Instead of finding fulfillment, a lot of people end up chasing entertainment: sports betting, Pokémon cards, meme coins, prediction markets. This is risky and empty.

The low-risk strategy of index funds is fine. But there’s something shallow and ephemeral in investing in volatile digital assets that are entertainment-first, meaning-second. If we focus on the smaller “fun” money, the better question is: what would be the most meaningful way to invest this?

I recently met someone who runs a crypto hedge fund who now reinvests his earnings into local restaurants. It’s his way of transforming low-meaning money into high-meaning money. He already loved these spots, had relationships with the owners, and now he’s financially tied to them too. When he goes out to eat, he catches up with the manager and knows he’s supporting something that matters to him.

Same for me with Dandelion Chocolate. I’m a tiny part-owner of this San Francisco chocolate company, and every holiday, it’s a no-brainer to buy gifts from them. I feel like I’m on the team. Plus, who doesn’t like nice chocolate?

The fact that people will spend thousands and endless hours researching Pokémon cards and meme coins suggests we’re starved for meaning. We need more pathways to connect money with belonging. One way is by enabling local businesses to raise funds from residents. Financial investment can deepen community, not just extract from it.

My version of dystopia looks like my first year in SF. The closest grocery store was Safeway, the coffee shop was Starbucks, and no one talked to their neighbors. Flip that, and utopia looks like a city full of local businesses, paying reasonable wages, supported by customers who might also be small investors.

What I’m imagining isn’t some Mafia or Yakuza-style ownership ruling with an iron fist. It’s a bunch of high-paid professionals in their late 20s to 40s, each chipping in a few thousand to have collective minority stakes in their favorite coffee shops, yoga studios, bookstores, and restaurants.

It’s counterintuitive: using money as a means to create flourishing communities.

(If you think idea has legs, hit me up)

Reimagining Education

I’ve been thinking about what kind of education I’d want for my future kids. I went to public school in Fairfax County, Virginia, which gave me a strong foundation. But I’m not convinced the default model is the most effective. Forcing 30 kids to sit still while one teacher lectures the same thing to everyone doesn’t make sense. Smart kids should be able to move faster. Struggling kids deserve more attention.

What I imagine is a mix of ambition and support, like the best parts of elite public schools, without the cutthroat intensity. And with the holistic values I’ve seen in kids raised in places like Hawaii, San Diego, or Colorado. I’ve thought about homeschooling or forming a pod, but that can lead to isolation or low social skills.

A couple months ago, I sketched out my version of the ideal school day: two hours of personalized learning on a computer, powered by AI, followed by the rest of the day outside playing with other kids. Basically a playground with two hours of video game-like learning.

Then I found out this school already exists. It’s called Alpha School.

It’s a chain of private schools around America where students learn for two hours a day on the computer, then spend the rest of their day on projects and activities. They use AI to personalize lessons, and even pay kids to learn. What stood out most to me is how much they encourage kids to dream big. One 5th grade class learned the economics of property management, then bought a house to manage on Airbnb.

If you want to learn more, check out this article, this podcast, and this first-hand review from a parent.

Intentions for September

This month, I want to continue to strive for simplicity and focus on fun. I feel like this month will be where we finally feel settled in. Namely, we need to get a dining table. I can already sense the shift is fully happening: the word routine has a positive connotation now.

I train jiu jitsu 3x a week, play basketball (indoors + full court = epic) 2x a week, lift 2-3x a week, and swim laps (slowly and outside) on Friday evening to clear my mind. Add on some career explorations, meeting 1-2 new people a week, trying a new restaurant on the weekend, and quality time with my girlfriend and friends and that’s a pretty full week.

There’s little desire to travel anymore. I sleep in a comfy king sized bed. I’m training jiu jitsu and biking around everywhere so I don’t end up becoming too soft. I eat ripe watermelon every day.

Life is good.

P.S. I’m a coach.
I help ambitious people find work that actually matters and design their version of the good life. If that sounds interesting to you, learn more here.

I’m deep in the middle of a dream when I hear a “eeeeee-oooooo!” howl that jolts me from mummy position in my sleeping bag into scrambling to gather my belongings. I didn’t bring my watch or phone with me into the wilderness, so this is my alarm. Pretty effective. From last night’s discussion, I know it must be just after 4:30 a.m.

I strap my headlamp around my beanie, zip open the tent fly, and dust off the ice flakes that formed on my backpack overnight. I join the other nine men at our designated “kitchen,” really just a flat area with a few rocks to sit on. While we take turns boiling water for our own rendition of oatmeal, I hold my hands around the camping stove’s flame, trying to stay warm at 11,700 feet in the Sierra mountains of California. It’s day three of our backpacking trip, and today we’re attempting to summit Mt. Sill.

Backpacking as Ritual

It’s hard to describe what backpacking means to me. It’s not quite a hobby or a passion. I don’t obsess over gear or dream about routes year-round. But when that narrow summer window opens, just after the snow has melted and before the storms arrive, I go. For some things like skiing or surfing, I can’t get enough. But with backpacking, one or two trips is all I need. In that sense, it feels less like recreation and more like ritual.

If a ritual is a practice of crossing from one world to another, then this is how I open a portal to a simpler, more intense way of living. The moment I leave my phone and wallet in the car, I step across a threshold. The weight of unread texts and emails is lifted and there’s a sense of freedom in knowing that there’s nothing to purchase, check on, or achieve. I’m just out there.

Out there, nothing is a distraction because everything matters. Wildflowers signal water. Distant clouds hint at rain, or worse. Sunlight itself can be a welcome blessing at dawn and a threat by late afternoon. You stop trying to be present and simply become so, because the environment insists on it.

Life gets simpler, but not necessarily easier. There’s no indoor temperature control, so you’re always adding or shedding layers. Your next move is dictated by the availability of water, the shifting weather, and how much daylight is left. You cook when you're hungry, sleep when you’re tired, and wake when the light returns.

When the sun goes down and you slip into your tent, falling asleep is near instant. There’s no need for a fancy evening wind down routine or melatonin gummy when you can actually listen to your body telling you it’s time to rest.

Urgency feels different here. It’s not the fake pressure of red notification bubbles or overdue emails. It’s simple and physical: get up the mountain before the sun gets too high, get back to camp before it gets dark. There’s no decision fatigue, no infinite list of options to analyze. Out here, the stakes are real and the needs are obvious. You know what matters, and that kind of clarity feels like strangely calming.

Synthetic Captivity

Now that I’m back, I notice how easily the conveniences of modern life can slip into control. What once felt like progress now feels like synthetic captivity. I’m grateful for the comforts: my bed, my fridge, transportation that isn’t just my feet. But I also see how these same comforts can dull the edges of experience. We’ve made life easier, but we’ve also made it too smooth. It’s so easy to split the bill at dinner that we all Venmo each other afterward, instead of figuring it out together at the table. It’s so quick to book an Uber that we’ve stopped asking friends for rides to the airport. Everything happens quickly, cleanly, and without friction. But friction is what gives us something to hold onto. When scrambling up steep walls of boulders, jagged edges are what keep you safe. You need the roughness to get a grip. Without it, you slide. Without it, life becomes so smooth you can’t hold on to anything.

I’m not trying to escape. I don’t want to live off-grid or make every day a test of endurance. But I do want to carry something back with me: a sense of how good it feels to live simply and fully, without any extra fluffy layers. I’m realizing that I don’t want a life of constant comfort, but one built with effort and imbued with aliveness.

When I think about a full life, comprised of many full days, it’s not one padded by endless ease. It’s one where I go to bed spent, and in the best way. Physically tired from moving through the world, mentally tired from pursuing something that matters. What’s strange is how often modern life delivers the opposite: a day of mental overdrive with no real movement, and still, somehow, the weight of unfinished tasks, unanswered messages, and a backlog of content waiting to be consumed. These days, it’s rare to end the day with your mind as quiet as your body is tired. The ongoing challenge I have presented myself with is to arrive at my bed each night feeling tired, fulfilled, and excited about tomorrow.

Pure Solitude

There’s being alone, like sitting in your apartment by yourself. Then there’s solitude, like going for a hike and spending time in your own head. But then there’s pure solitude. The kind you find deep in the backcountry, when you can’t see a single road, car, or skyscraper in the distance. It’s not just that you’re alone. It’s that nothing around you suggests the presence of other people. I might sound like a drug dealer promoting some purer version, but there’s really is something otherworldly about being that far removed from modern life.

I got a real taste of it on day four, when we spent the day in Palisades Basin.

The day before had been anything but peaceful. Climbing Mt. Sill was raw and exposed. The sun beat down hard, the air was dry and thin at 14,100 feet, and the ascent was a chaotic game of trying not to trigger an avalanche of rock. Every step required attention. We moved carefully, alert to every sound and shift beneath our feet, trying not to knock anything loose. It was the kind of environment where your body and your mind are entirely locked in.

The next morning, I woke up to the light and realized I had no water. I crawled out of my sleeping bag and hiked down a short but steep gulley to the nearest stream. At the bottom, the terrain had changed entirely. The sharp granite gave way to a soft, open meadow. The grassy fields were painted with yellow, red, and purple wildflowers. The sound of a running stream moved through the valley. I crossed it barefoot, stepping from the shady side into the sun. The warmth on my skin and the birdsong in the air made the whole area feel vivid with peace.

Later that day was our solo. Each of us spread out of view from one another for the entire day. In past trips, this kind of setting has dropped me into deeply meditative or contemplative states. But this time was different. I didn’t come away with realizations or insights. I also didn’t have anything major I was trying to figure out. Of course, there are still some big moving parts in my life, but nothing that felt urgent enough to bring to the mountains.

What I experienced instead was rest. I was so exhausted from the summit the day before that I kept closing my eyes the moment I sat or lay down. I moved between shady spots under pine trees and warm granite slabs, dozing off again and again, using my backpack as a pillow. I woke up once when a marmot ran across my arm, maybe thinking I was a rock or something edible. I also saw a hummingbird that day, zipping in midair with that high-octane energy that makes them seem like they exist outside of time.

In the afternoon, I wandered to a stream to fill up water and stopped to observe the wildflowers. I sat on a boulder overlooking the basin, scanning the sweep of mountains on the horizon and tracing the vertical rise from lush flowing valley to jagged granite peaks. Later, I spent time examining a pine tree, noticing clusters of red baby cones no bigger than M&Ms. Sometimes pure solitude opens the door to big internal shifts, but this time it didn’t. I napped with some trees, noticed some animals, drank some water, and ate some snacks. Nothing profound happened, but maybe that was the point. Some days, the most meaningful thing you can do is not try to find meaning at all.

When Money Doesn’t Exist

In the backcountry, everything is everyone’s. I borrowed a rain jacket and happily accepted other people’s trail mix, bone broth, and electrolyte mix. We all shared Jet Boil stoves, tents, bear-proof food sacks, and shovels that we used to dig holes for our poops. Normally, it might be kind of weird to ask another dude if you can use his chapstick, you know, because his lips have definitely touched the object you’re about to press to your own, but outside, no one gives a shit.

What’s interesting is how naturally this kind of sharing happens. If someone needs something and someone else has it, it just gets passed along. There’s no discussion, no accounting. And what I’ve noticed is that when people feel supported, they also become more willing to support others. It creates a positive flywheel. When you’re not worried about having enough, your attention shifts outward. You start looking for ways to contribute. No one is keeping track, but somehow everything balances out. The result is a kind of collective generosity that feels both practical and deeply human.

Back home, in our comfortable cubes, money is a deeply embedded concept that shapes almost every human interaction. It’s so ingrained in how we live that we rarely question it. We chip in gas money for road trips. We give money in the form of gift cards. Even something as simple as meeting up—whether with a friend or a stranger—usually comes with an indirect price tag: a coffee, a meal, something transactional.

There’s nothing wrong with these practices, but they can subtly shift how we relate to each other. Over time, they can blur the line between generosity and transaction. It becomes easy to forget that you can give something for free, just because someone else needs it. It doesn’t have to be as a favor or donated as some sort of tax write-off, but as an uncalculated gesture of care.

Money was created to make cooperation easier. But we don’t need money in order to cooperate. We can just help each other. The backcountry makes that obvious. With no modern conveniences, and everything carried on your back, there’s no space for extra. So you share. You rely on others. And somehow, it all works.

I’m not suggesting we get rid of money, even if I could snap my fingers and redesign society. But I do think there are plenty of places, even within the towns and cities we live in, where we can find ways to give, contribute, and support one another. Spending time in the backcountry just makes those moments easier to notice.

What Men Are Yearning For

Out in the backcountry, things feel raw. But they also feel safe. With the right group of guys, it becomes okay to talk about the things that usually stay unspoken. There’s no audience to perform for or workplace norms to conform to. Just ten dudes, shoulder to shoulder, doing something hard together. These are the conditions that opens the door to something deeper.

Over the course of the trip, it became clear that none of us had it all figured out. I mean, who does? Some were navigating transitions involving new cities, jobs, or relationships. Some admitted to working way too much. Others confessed they hadn’t fully appreciated what they had until this trip gave them space to notice it. Some felt the tug of guilt for leaving their partners and kids at home to be here. No one was pretending. That alone felt rare.

Back home, this kind of honesty is harder to come by. Men are suffering. Not always in obvious ways, but quietly. Drifting on autopilot and numbed out by screens, drugs, and work. The comforts of modern life start to cage us. Video games, porn, and information consumption offer stimulation, but not depth. It’s a subtle form of domestication. One that rewards comfort over courage, distraction over direction.

What I think men need is a kind of rewilding. Not a regression to some outdated past, but a return to the body, to movement, to real spaces with other men. Not bars or brothels, but places like the backcountry, the gym, a fire pit, a trail. Somewhere you can wrestle, play, joke around, and also admit that you're exhausted, aimless, or afraid. I don’t see those as two ends of a spectrum. They come from the same place. When men are in environments where they can be fully themselves, that intensity and that vulnerability often show up together.

I’m not calling for a return to any earlier version of society. Not to the eras of oppression, nor to weird modern trends like #tradwife on social media. Manhood looks different for every man. It’s shaped by age, race, upbringing, sexual orientation. There’s no one way. But I do think there are some common threads: a longing to pursue something greater than ourselves. A desire to protect and support the people we care about. A need to push against our own edges and grow. These aren't outdated traits. They’re ancient, still alive, and maybe more needed now than ever.

What men are really searching for is something to commit to. A challenge that demands something real of them. A mission. A purpose. You could call it dharma. You could call it life’s work. It doesn’t have to be tied to career. But it has to be lived. It probably includes elements from our time in the High Sierra: time in nature, real movement, honest connection with other men, and the willingness to feel everything we were taught to suppress.

That’s what this trip reminded me of. The good life, at least for me right now, isn’t built on ease or comfort. It’s about choosing simplicity and intensity. I don’t need to keep up with trends, always be doing more, or constantly consume. I want aliveness. More days that feel like life in the backcountry. Simple, demanding, honest. And deeply worthy of rest.

P.S. #1 - A big thank you to Dom and the rest of the guys who made this trip so epic. I’m going to cherish the conversations, banter, and memories.

P.S. #2 - I’m a coach.
I help ambitious humans simplify, feel more alive, and do work that actually matters to them. If you're ready to explore that, you can learn more here.

It’s nice to have plans because then we have something to look forward to. But once you make a commitment, unless you end up flaking, you’re on the hook to stay excited. Not just for the main thing, but also all the supporting tasks.

For example: You might be excited about running a marathon in six months, but are you ready to run four times a week and sacrifice one day every weekend for your long runs? What’s really underneath the desire to run a marathon? Is it a sense of accomplishment? Being able to follow through on your commitments? Losing weight?

Find the essence and start there. Pursue that mission, but instead of in one massive future commitment, take it one day at a time. Starting today.

2. Reclaim your attention

Put the phone away. Turn off notifications. Delete social media apps.

First it was oil, then it was data. Now the most valuable resource is your attention. If you're not paying for it with money, you're paying for it with your mind. Social media feeds are engineered to hijack your focus and distort your sense of having enough. Watching endless highlight reels trains your brain to feel behind.

Don’t charge it by your bed, otherwise you’ll impulsively check it first thing in the morning and doomscroll at night. Move your charger to another room as a starting action. Need an alarm clock? They still make them. I even linked it for you.

3. Interrogate your “but’s”

You might want to slow down, but you're worried about the tradeoffs. What if you lose your edge—your ambition, your momentum? What if slowing down means missing out, being left out, or falling behind

But falling behind on what, exactly? Keeping up with the Kardashians? I don’t give a shit about Love Island or what the latest TikTok dance trend is. But I do care about not wasting my life trying to keep up with things that don’t actually matter to me.

Interrogate your “but’s” and “what if’s”. We often frame everything as a tradeoff: rest or achievement, slowness or success. Are you stuck in an either/or? Either I go fast and win, or I slow down and lose. Either I’m productive, or I’m lazy. But what if that’s a false choice?

What if slowing down doesn’t mean giving up? What if it’s not a tradeoff at all, but a reorientation? What if slowing down is exactly what makes you sharper, steadier, stronger?

4. Upgrade your fuel source

What’s driving you? Is it money? Status? A hunger to feel worthy, to belong? How do you relate to yourself when you’re not moving forward? When you’re not producing or earning?

Striving can feel amazing… until it doesn’t. Securing the bag, getting shit done, chasing the next milestone—it works, until it starts to hollow you out. And when it does, things break.

The shift away from that kind of fuel is gradual. It comes with setbacks and relapses. I’m still working on it myself.

Athletes talk about playing “for the love of the game.” Missionaries serve from devotion. A dad works long hours because it means putting food on the table for the people he loves.

Operating from fear, insecurity, or not-enough-ness is dirty fuel. It burns fast, but then it burns out. Love and purpose are cleaner alternatives. They're just as powerful, far more sustainable, and if you stay connected to yourself, they’re infinitely available.

5. Feel enough

It’s not as simple as reading a little blog post and thinking your way out. You have to actually feel it yourself.

Modern Western culture tell us that consciousness lives in the mind, which leaves the body treated like a meat sack or visual apparatus to attract a mate. That’s wrong. The body isn’t just along for the ride—it’s an integral part of the whole, and it’s far more intelligent than we think.

The body stores memories in the form of emotions. It’s often closer to truth than the stories that your mind makes up. That’s why it’s so tortuous when you believe something in your head, but you know it’s not true at a deeper level.

Feeling enough means landing in a quiet place of inner abundance. Yes, your bank account might be low and the future might be wildly uncertain. But your body can still recognize: you’re safe right now.

This isn’t something to force or effort your way through. There’s no A+, no checklist. Feeling enough starts when you slow down enough to be with yourself.

6. Prioritize what really matters to you

There’s no shortage of prioritization frameworks: Eisenhower Matrix, RICE, Impact/Effort. As a product manager, I’ve used them all. They’re helpful for team projects, but when it comes to your life, these frameworks miss one crucial thing: the source.

Who is this priority coming from? If it’s your boss or a real obligation in work, that’s fine. But when it comes to your personal life, how much of what you do is actually for you? And how much is inherited from your friends, family, industry, or society at large?

René Girard called this mimetic desire. We want what others around us want simply because they want it. Spend enough time in any group, and you’ll start chasing the same milestones without even realizing it.

The result is overwhelm. That familiar sensation of being stretched too thin, rushing through to-do lists filled with things you’re not even sure you chose.

Real prioritization is about subtraction. It’s about questioning the “shoulds,” and letting go of the things that don’t actually matter in the bigger, grander picture. It’s as much about saying no as it is about saying a full, wholehearted yes to what truly aligns.

Not everything deserves your time.

7. Simplify

There’s a difference between complicated and complex. A complicated system has many parts, but it can ultimately be figured out, like filing taxes or assembling IKEA furniture. A complex system, like an ecosystem or a human life, is full of interdependencies and surprises. It can’t be solved. It can only be lived.

Why does this matter? Because we often get it backwards. We try to solve the complex with spreadsheets and hacks. And we let the complicated, like calendar clutter, indecision, or meal planning, slowly choke the joy out of our day.

I say: Let the complex be complex. That’s life. But simplify the complicated wherever you can.

I want my life to be simple. Not because I’m a simpleton, but because I want to make room for the things that are beautifully complex. I want to ponder philosophy and seek the sublime, not worry about I’ll sleep or what I’ll have for lunch.

At the core, all I really want is to be healthy, to have deep relationships, and to wake up with the freedom to spend my days in ways that feel meaningful. Simplicity helps me hold onto that. It clears the noise so I can stay close to what actually matters.

8. Give yourself permission to do things you enjoy

It’s remarkable how good we are at not letting ourselves do the things we actually enjoy.

Somewhere along the way, we picked up the idea that joy has to be earned. First you finish your homework, then you get a cookie. First the chores, then you can go outside. But now the homework is endless work, and the chores never end. They’re not even cookies anymore. They’re nourishing things like hiking, making music, or learning something simply because you’re curious.

What got you here might not be what gets you where you want to go. The reward loop of performance followed by permission may have served you once. But eventually, it gets in the way.

You don’t need to accomplish something first. You don’t have to earn joy. You just have to allow it.

Doing things for the sake of it helps us realize that not everything has to be like work. Internal enjoyment doesn’t need to require the prerequisite of external achievement.

9. Enjoy fully

It’s hard to slow down if you’re not enjoying your life. If nothing feels great, it actually makes sense to stay busy working, pushing, and distracting yourself.

But odds are, you already have things in your life that could bring you joy. A simple meal, good music, access to every movie or show ever made from the comfort of your home. We live in an age of abundance, but we’ve forgotten how to enjoy simple things.

We eat with one hand while scrolling with the other. We watch three different sports games at once—one on the TV, two on the laptop—while tracking bets on our phone. We numb instead of savor. We pop Skittles when what we really want is a ripe juicy peach.

Part of slowing down is resetting the threshold for what brings you joy. You don’t need a better plan, a bigger experience, or the perfect setting. You don’t need to chase something new to feel good again. Often, it’s the humble, repeatable things that when experienced while present restore us the most.

Enjoyment isn’t about adding more. It’s about doing less, but noticing more. And the more you enjoy fully, the more you start to notice just how many moments you’ve been skimming past.

For me, it started with meditation. Then it was walking without my phone. Then it was learning how to pick the best watermelon. Sweet, crisp, with no mealy spots. Enjoyment doesn’t have to indulgent or gluttonous. It’s a practice. And it’s available everywhere, if you’re paying attention.

10. Tend to your nervous system

This might sound like optional self-care, but it’s actually foundational. We weren’t built to sit in front of screens all day, locked in our heads and disconnected from our bodies. And yet, that’s where many of us live; tense, shallow-breathing, overstimulated, and wondering why we feel so off.

Your nervous system is your internal control center. It tracks whether you’re safe or under threat. Back in the day, that meant lions or starvation. Now it’s Slack notifications, news alerts, or the endless pressure to be doing more. Even if you're physically safe, your body may not feel it.

If you want to slow down, you have to show your nervous system it’s okay to do so.

Start by breathing. Slowly. Shallow screen-breathing keeps you in a low-grade stress state. Movement helps. Walking, yoga, stretching, dancing, or going outside without your phone. Try yoga nidra. It’s my favorite way to downshift.

If slowing down feels hard, it might be because there's something you're unconsciously avoiding, like grief, shame, or anxiety. These emotions can’t be outpaced. But they can be metabolized, slowly, when your system is ready.

Tending to your nervous system is not a luxury. It’s what makes slowness possible.

11. Mark time with ritual

Time is an interesting thing. On one hand, it’s made up: hours, minutes, days. But on the other hand, we experience time less as a concept and more as a felt sense. It stretches and contracts. Waiting in line at the DMV feels like an eternity, but a deep conversation with a friend can zoom by so effortlessly.

Days start to blur when we run on autopilot. We sprint from Monday to Friday, cram our fun and rest into the weekend, and then brace ourselves for the Sunday Scaries. It’s a rhythm, but it’s not exactly natural.

Long before smartphones or hyperconnected work lives, people marked time through ritual. Daily rituals created soft boundaries in the flow of life with slow mornings, shared meals, evening walks. Larger rituals marked thresholds: childhood to adulthood, single to married, life to death.

Ritual doesn’t have to mean incense, chants, or evil spirits. It just means doing something with intention. Drinking tea in silence. Lighting a candle before writing. Going for a walk at sunset every day to let the body know it’s time to wind down.

By ritualizing small moments, we’re practicing the art of noticing, appreciating, and anchoring ourselves in time. It’s how we make the invisible visible. It’s how we slow down enough to feel where we are.

12. Work intensely

Working hard is a vital part of life. Laziness isn't rest; it’s avoidance.

At first glance, working intensely might seem incompatible with slowing down. But it’s actually the shallow, scattered, always-on kind of work that burns us out. True impact comes from caring deeply and focusing your energy, not from constant activity.

I still want to be a high performer. I want to hone my craft, improve, get stronger, build better products, write better essays, and coach more powerfully. There’s nothing wrong with performance itself. It’s the identity of being a performer that gets slippery. One is an action. The other becomes a mask.

When I work on something that matters to me, it feels even better to go all in. The more I care, the more I want to raise the bar. And the more I raise the bar, the more focused and alive I feel.

In some ways, our tendency to stay busy or distracted comes from not going deep enough. We half-ass things, then wonder why they don’t satisfy us. But when you’ve worked intensely, when you’ve given something your full attention and energy, slowing down doesn’t feel like a guilty indulgence. It’s the natural next move. You don’t have to force it. You just do it.

That satisfaction hits different. After a real workout or deep work, you don’t want to doomscroll. You want to rest. Your body wants to recover and your mind feels empty. The urge to numb fades. When we work in a way that’s natural, rest comes naturally too.

This is how we come into the world. Babies play with full intensity, eat when they’re hungry, and then rest without hesitation. The real challenge isn’t whether to work hard or slow down. It’s to find work that feels like a game worth playing.

13. Live seasonally

Sometimes it’s easy to forget we’re animals.

But we are. And animals live in tight relationship with their environment. They eat when food is abundant, migrate when it gets cold, and rest when it’s time to rest. The seasons shape everything they do. It’s not a debate or a Huberman protocol. It’s instinct.

Living fully like an animal isn’t practical. After all we have jobs, social norms, and grocery stores. But I’m not sure that sitting in a box all day, staring at screens for both work and leisure, is the answer either.

Slowing down in a world that keeps speeding up requires returning to something deeper, something older. Living seasonally is one way back to our natural rhythm. You don’t have to escape to a cabin or move to the woods. You just have to start noticing.

Summer brings long days and warm air, which might invite more wandering, more swims, more unstructured time. Winter brings short days and low light, which might ask for slower mornings, quiet evenings, books, or knitting if that’s your jam.

Do what feels natural, and you’ll start living more naturally. And living more naturally almost always means slowing down.

When you live seasonally, you begin to notice change. You see how your environment shifts in subtle ways. You see how you’re shifting too, often faster than you think. That noticing builds trust. And that trust helps you slow down.

The Tao Te Ching says “Nature does not hurry, yet everything is accomplished.”

14. Let life surprise you

One reason we resist slowing down is the belief that we need to keep grinding to create opportunities and make progress. We see our goals on the horizon and, being smart and capable, map out the exact steps to get there. This approach can work for simple, linear goals: train for a race, get a certification, save a certain amount. But when it comes to the complexity of life, it starts to break down.

Think about it: how much of your life has actually unfolded according to your carefully laid plans? How many of your biggest turning points came purely from strategy and effort, without help from other people, unforeseen timing, or plain old luck?

I landed my dream job, but got laid off 10 months in. With barely a year of experience, I job hunted in the middle of a pandemic and took the first offer I got. It was remote, with odd hours and its own challenges, but it also gave me winters spent skiing and months living in Hawaii—experiences I’ll always cherish. I couldn’t have predicted any of it, and that’s the point.

Life includes forces beyond our control. Call them blessings, chance, karma, chaos. Whatever your framing, they’re real. And acknowledging that is both humbling and freeing. It means you don’t have to do it all. You don’t have to fill every hour with output. You don’t need to scheme your way to the next milestone.

Instead, you can start to make space for serendipity, synchronicity, and the creative sparks that arrive when you stop trying so hard. Sometimes slowing down is the most intelligent move you can make.

15. Move slowly

You can’t read a blog from some dude on the internet and expect to slow down by tomorrow. This isn’t a checklist or a competition. Some of these ideas might feel natural, others might bring up resistance. That’s okay. Real slowing down happens through direct experience, not intellectual agreement. So don’t rush to try everything at once. Pick one and try it out. Feel it in your body, not just in your head.

P.S. I’m a coach.
I help ambitious humans slow down, feel more alive, and do work that actually matters to them. If you're ready to explore that, you can learn more here.

Personally, I’ve kept my marital views intact—still hoping for a long-term, monogamous partnership (no sister wives, and with any luck, no divorces either). But when it comes to work and residence, I’ve embraced something more fluid. Like many others, I’m learning just how much agency we actually have over both our careers and where we live.

Work, in particular, has seismically shifted.

Decades of questioning the default path have culminated in quiet quitting, sabbaticals, and portfolio careers. AI is automating knowledge work while humans are craving more meaningful work. I’ve written about my own winding path, from quitting tech to sabbatical to career transition to an integrative approach that remains open-ended.

But this post is about another pillar of modern life that has opened up: place. While I’ve spent a lot of time exploring work and the inner terrain of self-discovery, I’ve also poured just as much energy into experimenting with where (and how) I most feel at home.

Lately, after signing a lease and putting down roots, I’ve had time to reflect.

The past few years have felt like an emotional rollercoaster with flips, corkscrews, and surprise drops—all on 2x speed. I’ve experienced the intensity and fullness of speedrunning a decade’s worth of adventures into three. I’m not married and I don’t have kids (or even a dog) and yet, I feel oddly contemplative. I’m 28, with a healthy mind and body, so it’s strange to feel like I’ve already lived a full life even though I’m still at the beginning.

I attribute this to pursuing life at full speed, made possible by the lack of a lease and the willingness to wander off the default path.

Over the past 5+ years, there’s been a lot of movement, both figuratively and literally.

Although the bulk of these winters have been spent skiing, NYC has been a central pillar throughout. I first arrived in NYC in 2020, and since then, I’ve spent anywhere from one to five months a year in the city.

I’ve become an expert at the tactical game of hunting down sublets and a student in the softer art of understanding how my environment shapes me, and how to create a feeling of home wherever I go.

I’ve wanted to revisit my experience of living in NYC because I just know that there is so much richness to mine for.

I’ve lived in neighborhoods across boroughs, from new luxury buildings that use an app to unlock the door to borderline illegal apartments that require earplugs and an eye mask to fall asleep.

I have lived multiple lives all on the same urban soil of NYC. I’ve slept in $10M penthouses and also stayed in rooms that could be confused for Shaquille O’Neal’s shoebox. One chapter came with an Equinox membership in Hudson Yards and an Amex Platinum card. And then the sabbatical version. Quieter, simpler, filled with home-cooked meals and public park hangouts.

Each sublet revealed a new neighborhood, and a new version of me.

A Tour of NYC, Sublet Edition

This series of sublets has taken me to every corner of NYC, with each stranger’s home offering a new lens into the city, and into myself. Across nine neighborhoods, I experienced the city in nine distinct ways.

There was the grimy hustle of the Lower East Side and East Williamsburg. The baby strollers and landmark parks in Park Slope and the Upper West Side. The immigrant communities of Chinatown and Sunset Park, where the food felt like home but the language still felt somewhat foreign. And the polished pace of Dumbo and Flatiron, where wealth, speed, and ambition saturate the streets.

In between these stints, I wove in time in ski towns like Tahoe and tropical paradises like Hawaii. Each new setting required me to recalibrate, recreating new routines and expectations to match the environment. The stark contrast between places forced me to prioritize what I needed in each season. Each time I returned to NYC was a choice: a conscious swap of quiet mountains and slow beaches for chaotic concrete.

I wasn’t aware of it at the time, but the city was acting as one giant mirror, reflecting and amplifying whatever was going on inside me.

With its sheer scale and constant motion, the city met me exactly where I was at. In the early years, that meant hustle and overstimulation. I chased belonging and recognition. I filled my schedule with work and social plans, staying busy enough to quiet the anxiety, at least during the day. At night and in the early morning, it would always reliably return.

But things started to shift.

As I began to untie my desires from companies and peers, I discovered new ambitions that felt more authentic and less performative. In response, the city transformed. It became a breeding ground for creativity and self-expression. My image of a “New Yorker” shifted from Manhattan magnate indulging in mainstream trends to the Brooklyn weirdo who didn’t give a shit. I wanted to feel that free in my own skin.

Eventually, I reached a new kind of confidence, but it wasn’t because of wealth or physical appearance. It came from the spaciousness of my sabbatical, allowing me to live closer to my values. As I created distance between me and my former job title, the city became a playground. Its constraints felt less like walls and more like a jungle gym: a structured set of obstacles to move through, climb on, and explore. Every credit card swipe, every RSVP became a mini-experiment: What do I really care about? What am I okay living without?

Through all this, the city’s real gift emerged: the people.

I’ve been referring to NYC as a place, but it’s really the people who showed me the many selves I could live. I sought out a wide range of characters, always curious how they lived. I met finance power couples in $8K apartments, retail workers barely scraping by, tech bros completely wrapped up in their work, and creatives who resisted being labeled by anything.

Through them, I saw the butterfly effect of my own choices. Life could look so different with just a few small bends in my path. These weren’t just people passing through my life. They were mirrors, reflecting the lives I didn’t live and the versions of myself I didn’t become.

The Intention Behind the Effort

In NYC, I learned that effort is rewarded. By effort, I don’t mean grinding late at night at the office to earn praise or avoid criticism. I mean a form of energy expenditure that comes with care.

I line up and wait for three hours, and then I savor the best pizza in the world at Lucali’s. For 14 weeks, I run four times a week, anywhere from 3 to 22 miles, and then I revel in the communal ceremony of the NYC marathon. When I’m on the verge of quitting my job, I don’t escape with a vacation. Instead, I take a week off and still go into the office, working tirelessly on personal projects.

The returns on authentic effort are limitless.

Counterintuitively, NYC taught me to value material possessions less and shared experiences more. It’s easy to assume you need to spend big to enjoy the city. And yet, I found the opposite to be just as true.

Rotating rapidly through tiny apartments taught me to live with less. The small spaces nudged me outside, to go seek others. My most vivid memories are of cozy dinners at home, long walks through neighborhoods, and picnics in parks—not shopping sprees in Soho.

Living in New York taught me that ambition alone isn’t enough. It has to be self-directed.

The city is saturated with hustle, but not all hustle is generative. I saw investment bankers grinding 80-hour weeks with no end in sight, stuck in golden cages they weren’t willing to leave. I met remote workers who spent most of their time indoors, disconnected from all the city has to offer. But I also met artists and entrepreneurs who treated the city like a chessboard, playing with curiosity and intention.

New York taught me the difference between authentic effort and blind hustle, and that anything is possible when you learn to shape your time, not just fill it.

The Anthropology of Space

Whenever I live in someone else’s home, I find myself subconsciously absorbing details about who they are. Through inhabiting their curated space, questions begin to surface:

How does this person live? Do they cook often? How much free time do they have? What do they care about? Do they like to host? What possessions do they treasure most?

Their home becomes a quiet conversation. A reflection of values, habits, and the shape of their daily life.

In turn, the space poses questions back to me:

What do I need to feel comfortable? How do I inhabit this space differently from its owner? Does it feel like home? What’s missing? What would I bring from this space into my own future home? What does this environment invite me to do—or not do? Is there space to rest, to create, to connect?

Living across all these different neighborhoods and configurations slowly revealed a few simple truths about the role of place. Paradoxically, where you live matters a lot, but also, not that much. It determines who’s nearby, and therefore who you spend time with. But in a city like NYC, it’s so easy to get around and opportunities are always in motion.

Some homes inspired me, like that girl’s one bedroom on the edge of Soho and Chinatown with the Noguchi coffee table and massive Monstera plant. Other spaces, like my cramped room in Dumbo that I shared with a stranger, didn’t—so I spent all my time outside the apartment.

When places came equipped with kitchen tools and sufficient square footage, I leaned into hosting dinner parties. When it felt burdensome, I branched outward, seeking connection in other spaces. I was in constant conversation with my surroundings, noticing what pulled me and letting that guide how I moved through the day.

Long morning walks were easy when I lived near Sunset Park, Prospect Park, and Central Park. But in Flatiron, LES, or Chinatown, I didn’t force it. Stepping outside meant immediate stimulation, so I found other ways to start the day.

Over time, I realized how much I could shape my experience within any given place. But I also uncovered a few non-negotiables. At the top of the list: sleep. It’s the single biggest factor in how good I feel. I slept better in humble Sunset Park, on a mattress on the floor, with earplugs and an eye mask, than I did in a multimillion-dollar Flatiron penthouse where the bed was so soft that I’d toss and turn all night.

The other two essentials are fitness and food. At the start of every sublet, I’d immediately scout for nearby gyms and grocery stores. I weighed my options carefully. Affordability was nice, but I often went out of my way, financially and logistically, for a better workout or more nourishing food.

Through nine sublets, I learned that sleep, movement, and nutrition form the foundation of my wellbeing. It sounds simple, and maybe even obvious, but it took experiencing life at both extremes to truly internalize it.

On the surface, subletting is a flexible way to live lightly and save money. But at a deeper level, it taught me how to be an anthropologist of space. Instead of studying the masses through a historical lens, I was learning about individuals through immersion in their everyday environments.

By studying how others live, I’ve learned how I want to live.

Ready for Departure

During the past six years of nomadic living, I spent a lot of time carefully deciding where to live, and when. Winters were reserved for skiing, a seasonal rhythm with the dual benefit of letting me escape New York’s harsh cold. I love the cold when I’m gliding on snow, not when I’m getting blasted by city wind.

I always knew that I’d eventually want to settle down somewhere, I just didn’t know where. I spent countless hours daydreaming, vividly imagining myself living in Hawaii, Tahoe, San Francisco, and even staying in New York. The freedom to choose was also paralyzing. Every possibility came with its own set of trade-offs, making optimization a futile endeavor.

Choosing to leave New York was intentional, but also an act of surrender. I’ve asked myself "Where do I want to live?" more times than most. Over time, I’ve gotten good at sensing when a place fits. Maybe we’re not so different from other migratory creatures after all. Whales cross oceans through a mix of biological clock and environmental cues. Birds travel thousands of miles, responding to shifts in light, magnetic fields, and even the stars above.

For me, there was a similar internal signal. New York no longer felt right. The intensity that once energized me had started to wear me down. I’ve become more sensitive to my environment and more guided from within. With a clearer sense of where I’m headed, I find I no longer need billboards directing me or late-night hustle to get shit done.

Along with that shift came another realization: pure drive isn't everything. There’s wisdom in slowing down and simplifying. With fewer options comes less noise and fewer distractions, making it easier to hear what I really want.

And In the end, it wasn’t even up to me.

My girlfriend matched for residency, which decided both when we would leave and where we would go. It’s funny how after years of obsessing over where to live, my answer came not from more mental gymnastics, but from something outside my control. And yet, when the time came to find out, I wasn’t anxious or fixated on the outcome. I had already accepted that the where matters less than knowing how I want to live.

Living Well, Wherever

I still stand by the idea that where you live is one of the most important decisions in life. But my view has evolved. I used to think of a city as something that imprints itself onto you, with its culture, energy, and habits shaping who you become. Now I see it more as a relationship. It's not just about the place itself, but how you respond to what it offers and withholds.

It’s easy to believe that a new city will give you what you’re missing. And sometimes it can. But I’ve come to trust that wherever I end up, I’ll be able to notice what’s missing and move toward what matters. I’ve let go of the fantasy that any one place will be perfect. What matters more is having the awareness to observe and the intention to act.

Maybe that’s the whole thing: where you live can change your life, but it’s not everything. If you feel stuck, it’s worth asking: is it really about the city? Or is it something deeper? A certain kind of friend group? A romantic partner? A healthier lifestyle? More fulfilling work?

Moving can be the move. But often, all it takes is a subtle switch-up. A single conversation with the barista can spark a sense of belonging. A new gym can bring you closer to your people. A different apartment brings new neighbors, deeper rest, and a fresh perspective.

I still believe in experimenting with new ways of living. But if there’s one thing I’ve learned, it’s that the cliché is true: we go on the outward journey searching and searching, only to find what we were looking for was within us all along.

Speedrunning New York was a serial adventure that taught this: Where you live matters. But how you live, wherever you are, matters more.

P.S. I’m a coach who helps people live bigger, more authentic lives, especially during seasons of change. Learn more about my coaching here.

In May, I traveled from coast-to-coast and then across the pond. I began on the northern California coast, at a retreat1 nestled in the redwoods of Mendocino. The community was loosely organized around entrepreneurs exploring consciousness and spirituality, but the actual experience of being together felt far more authentic than any label could capture. Surrounded by people with both conventional success and deep spiritual practice, I left feeling inspired. It reminded me that I don’t have to choose those two worlds, and can instead keep walking the tightrope of integration.

Back home, I packed my carry-on for one last big trip—or really, a series of them. First stop: New York City, likely the last time I’ll live there (though I’ll definitely keep visiting). We celebrated my girlfriend’s graduation from medical school, and I hung out with friends—accompanied by the unusual feeling of not knowing when I’ll see them next. I’m deeply grateful to NYC, my seasonal home for the past 5 years. It’s where I learned to dream and where I came to understand the currency of ambition.

After a full day of graduation festivities, I boarded a midnight flight to Rome. I spent the first few days in a hostel, chasing the nostalgic wanderlust of my early 20s—when I backpacked through SE Asia, Patagonia, Europe, and Morocco. The hostel served dinner each night, ranging from free to a few euros. On my first evening, over paper plates piled high with free “salad rice”, I met a few fellow travelers.

I met a young guy who’d just quit his job as a windshield repair tech2 to travel the world until he ran out of his $20K in savings. I felt inspired, partly in the vicarious sense, but also from a place of self-gratitude. I remembered my younger self who once prioritized adventure over stability, community, or dating. Back then, I wasn’t sure if it was the right call. But now I’m grateful for the memory bank of sublime moments and borderline reckless stories I get to revisit.

Once my girlfriend flew in, we spent ten days roadtripping through Tuscany, hopping from one rustic Airbnb to the next. I arrived carrying the residual busyness of the past months, eager to soak in the slowness of Italian life. It was my first time in Italy, and I found myself wondering what factors fuel American perception that Europeans live with more leisure and less hustle. Was it the weather? The wine? The late dinners that stretch into midnight?

I noticed a few things. Grocery stores and cafes were much simpler. I went out for dinner and was warned (twice) that I would only have an hour to eat before the 9pm reservation arrived. I ordered a pasta and a side of boiled escarole, not realizing that each course is served and eaten separately. As I sat there with just a lone plate of veggies in front of me, I felt oddly quiet. As a Chinese-American, I’m used to meals where dishes arrive all at once, so they can be eaten together and flavors can mix freely. But here, the simplicity of the structure made it easier to slow down. And that’s something I wanted to bring back with me.

In Florence—the birthplace of the Renaissance—I found myself wondering if the claims are true: are we living through a second one? As we wandered the halls of the Uffizi Gallery and Palazzo Pitti, I thought about what a modern Renaissance figure might look like. Who (or what) would be today’s Medici family? And what are the new mediums of storytelling and creativity, now that painting and sculpture have evolved into pixels and code?

I left Italy both relaxed and ready. It was the first true vacation I’d taken in months. Even with the flexibility and freedom to shape my own schedule, it’s been surprisingly hard to unplug for more than a few days. This time, I wanted to be fully present, so I rescheduled all my coaching sessions and kept my laptop off. For someone self-employed, that wasn’t easy.

With NYC and Italy complete, my final stop was Asheville, NC for my Hakomi therapy training. After several weekends of all-day Zooms, meeting my fellow students in person was a true delight. I couldn’t remember the last time I’d learned something without a screen, or how fun it is to practice skills that require no tools, no tech, just attention. Spending five days in the company of therapists, yoga teachers, bodyworkers, and other coaches felt refreshing—a different crowd than I usually find myself in. We’re only halfway into the training, but I’m already starting to explore how to weave Hakomi into my coaching practice.

Back in California, my whole system let out a sigh of relief. With no more travel on the calendar and my first yearlong lease in six years on the horizon, stability was finally in sight. But before we could move in, we got stuck in a holding pattern: a sprinkler had mysteriously gone off, flooding three vertical units and putting the building into restoration mode. It felt almost comically theatrical—that after months of movement and eager anticipation, one last obstacle stood in the way of setting down.

One week after our original move-in date, we arrived eager to compare imagined future to actual reality. The property manager pointed out where our movers could park (we didn’t have any), then where we could park our U-Haul (also didn’t have one). After a few rounds of lugging suitcases and duffel bags containing the totality of our possessions from the car to the apartment, all that remained was the 100-pound, compressed king-sized mattress. We hauled it up the twisting stairs, unboxed it, and watched as it slowly unraveled in the middle of the bare bedroom.

Without a bed frame, sofa, dining table, or any other furniture, our new place looked rather empty on day one—but it already felt like home. That night, with the window open letting fresh air in, I slept soundly, at peace with the start of this next chapter. I was ready to call Palo Alto home.

P.S. I haven’t written much about what life here has actually been like, but that’s coming soon. For now, I’m slowly settling in and looking to meet new people in the area! If you're nearby (or know someone who is), I’d love to connect.

The 1000 Pound Club has haunted me since high school. As a freshman first touching barbells, I repeatedly told myself that someday I’d hit it. That “someday” stretched into years with a rotating cast of reasonable excuses. Every winter means ski season, relegating lifting to maintenance mode. Living via sublet to sublet made consistent training complicated even though I always found access to a gym. Eventually, this unfulfilled pursuit started to nag at me like an unpaid debt. I considered myself reliable and determined, but this one incomplete self-imposed goal continued to sit in my subconscious, whispering quips of self-doubt to me.

After years of half-assed effort and going through the motions, I decided to actually dedicate myself fully. This wasn’t a public performance. There was no marathon bib, Instagram transformation post, and I don’t even have videographic proof that I did it. Just me proving something to myself. The evidence of my prolonged procrastination exists in the form of an unchecked reminder “Look up powerlifting program to get to 1k club”, dated “3/19/24” in red text indicating it's been long overdue.

Earlier this year, after traveling through Asia in February and wrapping up the ski season, I finally confronted this lingering goal. No more excuses about travel or seasonal shifts. I was ready to hit the 1000 Pound Club. The commitment itself proved more challenging than an intense workout at RPE1 9. Physically moving iron is straightforward. Our ancestors have been lifting heavy objects since the caveman era. The real challenge was confronting years of self-deception, revealing the gap between who I claimed I could be and who my actions revealed.

For most of my life I have been a goal-oriented achiever. The dopamine rush of getting a gold star in kindergarten translated into consistently chasing straight As. Each 100/100 or A+ reinforced my identity as someone who completes things. Any missed points or incorrect answers triggered immediately going into self-improvement mode to analyze and correct. That was just in the classroom. In sports, whether it was basketball or soccer, I was acutely aware of the scoreboard. In these games, it was always clear what the objective was, and I became a machine of goal-setting and goal-accomplishing.

Then came my sabbatical, a deliberate dismantling of this achievement machinery. I had to unlearn the rigid goal-setting adherence that once got me praise, progress, and pride. I stepped into the unknown without any future-oriented outcomes, learning to navigate by intuition rather than objectives. I immersed myself in a philosophy of process over goals, reading about the virtues of goalless exploration from indie bloggers and self-help authors advocating this approach. While this liberation from goals brought necessary healing, I eventually discovered its limits. Complete goallessness across all domains left me adrift, passively waiting for life to happen instead of creating forward momentum.

The way I see it, sometimes goals have their place. In the right context, a clear, measurable objective becomes a powerful tool rather than a burden. My approach to lifting went from casual sessions based on what “felt right” to structured programming with progressive overload and periodization. I showed up consistently, regardless of motivation levels or how my body felt that day. Maybe I would’ve eventually hit the 1000 Pound Club without deliberate intention, but I think it’s unlikely. Committing to the goal itself became the bridge that carried me across.

The value of goals hinges on their context and intention. Pursuing external markers of success can trap you in a half-century long quest toward the wrong horizon, before waking up at 50, filthy rich yet completely empty. But self-authored goals offer a different trajectory. Clear paths of dedication and diligence can lead to effective change without inauthentic distortion. We contain multitudes, and different seasons and areas of life call for different approaches. Some benefit from strong structure while others need fluid spaciousness. The wisdom lies in discernment: knowing when to set a goal, and when not to. When properly applied, goals provide the scaffolding for us to transcend our self-limiting beliefs and ingrained patterns.

The Case Against Goal-Setting

We’ve been conditioned to chase targets from childhood. From standardized testing to literal goals in peewee soccer, we were taught that hitting goals was praised and rewarded. This formula works reliably through education and early career. While studying EECS at UC Berkeley, my most driven classmates zoomed through coursework into accelerated careers. Now in their late 20s, they’ve already reached director-level engineering positions, staff product roles, partner-level in VC, or founded their own companies. They appear satisfied with their trajectories, as they should be. Their achievement-oriented paths provided substantial safety nets to be able to apply leverage and take bigger risks, which is a genuine privilege.

But increasingly, I notice people diverging from these linear paths. Like a river delta splitting into countless tributaries, formerly single-track careers branch into unexpected territories.

I know a Google engineer moonlighting as a DJ who migrated from Singapore to NYC. An IT specialist who left tech to pursue comedy alongside Jake Paul. A lawyer splitting time between high-billing corporate work and fulfilling therapist training. A software engineer on sabbatical running underground bakery pop-ups. A wealthy post-exit founder searching for meaning beyond status competitions with peers. These aren’t hypothetical cases. These are real people I know navigating complex relationships with work, achievement, and purpose.

Major life milestones often catalyze further self-inquiry. I’ve noticed friends who recently got engaged or married naturally steering towards deeper reflections with their career. Perhaps having answered “who will I be with?”, they inevitably confront “what should I be doing with my life?”

As we grow up and wake up2, we’re exposed to more possibilities and external disruptions. The pandemic shattered our perception of what’s normal, made remote work the default, and gave people a new ideal workweek (not commuting to the office 5 days a week). When world leaders can snap their fingers to create geopolitical and economic shockwaves that result in layoffs and hiring freezes, and anyone can get lucky at winning the attention algorithm game on TikTok, it can be difficult to adhere to the rinse and repeat method of goal-setting.

Goal-setting works effectively in two specific contexts: aligning a team together towards a shared mission and achievement that can be done simply and linearly. Companies and sports teams benefit from shared objectives. Individual skills with clear progression paths, like weightlifting, also respond well to targeted goals.

But goals falter in complex domains with multiple variables and multiple players. Career trajectories and relationships resist this approach. Declaring "I'll secure job X by date Y" often backfires (I tried this recently and watched it implode.) Similarly, setting a dating OKR of finding your true love by Q3 also doesn’t work. As environments grow more complex and unpredictable, strategies must shift from rigid goal-setting to adaptive processing and responsive awareness.

When Goals Work

Goals thrive in simple, linear domains with self-contained feedback loops. Physical fitness is a great example with measurable progress and predictable improvement patterns. There were plenty of fitness goals to choose from, but for me, the 1000 Pound Club felt appealing. It’s a benchmark of strength with its binary clarity whereas a marathon has finish times, creating additional complexity. As I navigate my current season of uncertainty, this concrete goal kept me anchored and prevented aimless drifting.

I began training on March 20th with a decent baseline of 225x5 on bench, 250x5 on squat, and 315x5 on deadlift. With months of skiing and traveling, I hadn’t lifted consistently, and I also hadn’t tested my one rep max in years. My full potential remained a mystery.

I considered hiring a virtual strength coach to help me with programming, but I decided to go the DIY route and partner with Claude. First, I prompted it to generate a meta-prompt to synthesize multiple powerlifting methodologies. Then I fed it my preferences like how many training days per week, when I wanted rest days, and my target completion date. We also covered everything from warm-up protocols to nutrition to equipment recommendations. For these, I didn’t learn anything revolutionary, but at least it validated my existing approach even if it’s been mostly casually tossing around weight at the gym.

The bulk of my training happened in April while living on the Upper West Side. I found Strength Society, a local gym with the right vibes, unlike Planet Fitness with its heavy lifting bans and pizza parties. To eliminate friction, I created a Notion workout tracker and added a widget to my homescreen. The program I co-created with Claude was pretty solid with consistent progression and well-timed deload weeks.

My original plan targeted June 2nd for testing all three lifts, just before a five-day therapy training in Asheville where lifting would be inaccessible. But physical reality intervened. My left pec developed persistent tightness (not sharp pain, but concerning enough to research potential tears online.) After a couple weeks without improvement despite reduced intensity, I decided to just go for it. On May 1st, at a suburban Bay Area 24 Hour Fitness, I progressively increased my bench weight until hitting 285 pounds. I might’ve had enough juice to hit 295, but having reached my target range of 275-285, I played it safe. Adding wrist wraps mid-way helped provide support, and so did asking a stronger dude for a spot. His encouragement pushed me past what I would’ve attempted alone. Sometimes we dwell in our world of standards and thresholds that we need others to help raise the bar for us.

A few days later came deadlift day. I warmed up, started with one plate on each side, and quickly ramped up to 405. Seeing four plates on either side for the first time was a satisfying sight, but it wouldn’t mean shit unless it came off the ground. After hitting 405, I attempted 425. Whether from inadequate sleep or incomplete recovery, the heavier weight wouldn't budge. I dropped to 415, rested my central nervous system, and then lifted it..

With an upcoming retreat with vegetarian meals and glamping accommodations, I was confronted with the decision of whether to finish the project before I left or to wait until I got back. I didn’t want to take the chance that I’d return somehow with less strength and frankly, I just wanted to get the damn thing over with so I could stop LARPing as a powerlifter.

On May 7th, the day before driving up to Mendocino’s redwoods, I decided to go for it. By coincidence, the same guy who spotted me on bench was deadlifting next to me. With the confidence of my consistent training and a Starbucks caffeine boost, I squatted three plates on either side. The 315 squat meant my total reached 1015 pounds, exceeding my goal by the weight of a 6-month old baby.

Going into this, I precisely prompted and crafted a training plan with weight, sets, and reps dialed in for each workout. Initially, I needed Claude's programmed structure as external scaffolding for discipline. But eventually, I developed enough embodied knowledge to trust my own judgment and abandon the prescribed timeline.

I felt a sense of satisfaction that I had hit my goal. This was entirely self-driven. My mom was supportive but ambivalent. My girlfriend gently explained to me that brute strength isn’t actually the aphrodisiac that men imagine it to be. My powerlifter friend kept me in check, reminding me I was still weak by serious standards. Nobody particularly cared, which was good because that meant I could harvest all the glory for myself.

Setting Goals While In Transition

I’ve navigated countless transitions, including geographic relocations, career pivots, sabbaticals–and I’m currently in one right now. With roughly half my coaching clients also navigating work-life transitions, studying the psychology of transitions has become a central focus of my practice.

Common transition pitfalls come up repeatedly. The urgency to solve the money problem instead of sitting with uncertainty. The reflexive pursuit of external “shoulds” over authentic “wants”. The default to frantic busyness over genuine curiosity. And particularly relevant here: setting rigid deadline-driven goals when flexibility and spaciousness is needed most.

Transitions by nature involve complex, nonlinear environments saturated with uncertainty. When the path forward requires expanding possibilities rather than narrowing them, goals can become counterproductive distractions. The research-backed book Why Greatness Cannot Be Planned demonstrates how singular objective pursuit can actually prevent novel discovery and optimal outcomes. Similarly, The Pathless Path offers an intimate perspective for navigating uncertainty without predetermined destinations. In place of goals, I consider what I provocatively call Chainsmoking Good Days–identifying your version of a satisfying day and living one at a time without future fixation.

Remember how we learned "Stop, Drop, and Roll" for fires? Transitions deserve their own protocol: "Pause, Sense, Discern." When forward movement feels unclear, first pause to create clarity before impulsively acting. Then sense using your full perceptive capacity, not just rational thinking. Finally, discern whether the situation requires structured goals or a more experimental approach of wandering, trying, or simply waiting.

Transitions often require releasing goals prescribed by external voices that no longer resonate. The untethering from familiar benchmarks can feel really destabilizing. But abandoning artificial goals doesn't mean abandoning all structure. I'm not suggesting you stop brushing your teeth. Instead, notice what emerges in the space you’ve created. Ancient wisdom affirms that emptiness often precedes unexpected emergence. Realities that could not have been predicted or conceived of become possible.

Even with intellectual understanding, letting go of goals remains challenging. The disorientation can feel lonely, like an abandoned astronaut floating in outer space. Here's my counterintuitive recommendation: while navigating major transitions, set a clear goal in a secondary life domain. In my case, I chose a fitness goal for myself. While activities like cultivating mindfulness and developing self-awareness will help with being in uncertainty, I’ve found that partially taking your mind off of “The Main Thing” provides surprising relief. Since I was already spending consistent gym time, pursuing the 1000 Pound Club required no additional resources (except temporarily setting aside running).

So if you’re going through a transition or feeling a bit lost in life, consider committing to an exciting goal in a different domain. Something measurable, achievable, and personally meaningful. At minimum, you'll gain productive distraction from existential discomfort. At best, you’ll make continuous progress, savor the satisfaction of achieving your goal, and develop the vital capacity to honor commitments to yourself, a skill that will serve you long after this transition ends.

So… what goal are you ready to commit to?3

P.S. I’m taking a few weeks to chill out while I travel before I commit to a new goal :)

Yesterday was an interesting day. In this season of transition, I’m noticing how dynamic each day can be—similar to solo traveling in a foreign country. I have a sense of control over my life, but my curiosity pulls me in different directions, my routines voluntarily shift, and I’m learning to follow where my energy leads.

Here’s how yesterday went down: I spoke with three people from three different companies, each meeting arranged either through a mutual connection or inbound interest. I also caught up with my friend whose warmth and quirky spirit reminds me of how vital it is to embody authenticity. As a fellow coach, we jammed on everything from marketing to who we serve to the importance of healthy cofounder relationships in startup success.

In the afternoon, I drove to the foothills of Piedmont to meet up with an independent executive search recruiter (and her cool dog) who’s also going through a transition right now. As we ran up and down the trails surrounded by redwoods, sunlight filtered through the dense canopy, transforming the forest floor into a living patchwork of luminous patches and cool shadows.

Afterwards, to wait out the rush hour traffic, I decided to explore the Berkeley campus, my alma mater. Despite my sore legs, I made my way to the Campanile and Memorial Glade, watching seniors taking grad pics as past memories flooded back.

Later, I first heard, then saw, a rental RV crash into a brand new parked Tesla. A minute later, a tomato-tinted guy stormed out yelling someone’s name. I put together the context clues. The RV driver was in the same frat as the Tesla owner, and now both vehicles were badly damaged. I stood there for briefly, curious about what would unfold. Being a coach feels like being an anthropologist—studying humans in their natural habitat. In this moment, I witnessed the fascinating complexity of raw emotions.

I could’ve headed home, but I decided to have dinner at International House’s dining hall, a place that fed me countless meals for over two years during my college years. After my six mile trail run, I knew I’d get my money’s worth even at the non-meal plan rate. For $22, I refueled on orange chicken, sweet chili shrimp, overcooked broccoli, salad, and multiple bowls of cereal. Before leaving, I made a panini to-go, wrapping it in six flimsy brown napkins despite being too full to eat it immediately. As I walked to my car, I offered it to a shirtless homeless man nearby who reacted with intense anger for the disturbance and spat at me. Adrenaline rushed through my body, bracing me for physical contact that never came. I drove home while listening to a podcast, showered, updated my website’s copy inspired by my conversation with Amber, and went to bed.

In this period of flux, I'm learning that seeking what's next can beautifully coexist with fully experiencing the present.

Life Updates

• The third weekend of Hakomi training felt like a real turning point. We have now learned enough of the method to begin practicing, which is genuinely exciting. The day before the training began, I was on a six hour flight home from New York City, re-reading a few chapters of the Hakomi textbook. It reminded me just how powerful and even a little magical this method can be. Spending three full days (20 hours on Zoom) is not always easy, and being fully present can be a challenge. But honestly, I feel energized. I am excited to start putting this work into practice. I believe it has the potential to help a lot of people (myself included).

• Every year during my annual review, I'm surprised by how rich and full the year was. I tell myself the upcoming year will be more routine with fewer adventures, but since questioning the default and living life on my own terms, that hasn't been the case. For example: 2025 started with skiing in SLC in January, China and Japan in February, and navigating inner changes in March.

  • April was spent in NYC, living on the UWS. This was my last extended period in NYC, at least for the foreseeable future. It feels right to close this chapter. I first started living there on-and-off in March 2020 (not great timing). My view has held up: New York City is the city if you want to be ambitious and creative. San Francisco is superior for technology, but lacks the same density of eclectic souls.

  • I'm ready to leave the city, not because I'm sick of it. What I once sought externally from the city now lives within me. Everyone arrives in NYC bright-eyed and bushy-tailed, pursuing something. Through understanding who I am and reconnecting with my inner flame of ambition, I no longer need the outside world for that. Instead of a fast-paced ambition accelerator, I'm craving comfort, quietness, and nature. I already know where I'll be moving (and signing a lease!), but that's for a future blog.

• Big travel plans coming up:

  • Next week: a 3-day retreat in Mendocino with other entrepreneurial folks interested in spirituality and consciousness. When a trip comes together, there's this Gen Z saying "made it out of the group chat", but this is actually a highly organized gathering born from a group chat.

  • Afterwards, back to NYC for my girlfriend's med school graduation. I think nowadays we don't celebrate enough, so it'll be nice to have this occasion. (There’s more I could say here, but I’m choosing not to because I value privacy). I still need to figure out what to wear because...

  • I’m flying to Rome that same night for an entire week in the Tuscan countryside (send me recs!). During past trips, I found myself torn between immersing myself in the physical present world and being caught up in work. As a self-employed coach, I only get paid when I actually coach (no PTO), so making this choice isn’t as easy as just plopping down a week of “OOO” on my Google Calendar and submitting the dates on Workday. But I know it’s the right choice. I’m looking forward to people-watching like a time-rich old Italian man and hopefully eating a raw tomato so flavorful that I can never settle for the watery mass-produced versions that we have in the states.

  • Then I fly back to NYC for a night and immediately fly to Asheville for five days of Hakomi onsite training. That’s all the travels I have planned so far this year, and I’m glad.

Some Of My Ideas

Because ideas naturally emerge from my own mind, I rarely notice how varied they are. Seeing them all listed out like this reminds me of how weird and diverse my interests are. I’d love to hear your thoughts in the comments!

Transformational Community

Recently, two people on separate occasions asked me if I've ever considered starting a community. Prior to that, I hadn't given it much thought, although I have been "trying on" the term community builder after invited me to his C3 community builders conference, prompting me to reflect on whether I identify as one.

This community would fill the dire need we have in modern society for a sense of belonging and our innate need to be fully heard and seen. The decline of religion, hustle culture, social media, and hyper-individualized culture all contribute to this problem of not having spaces where we can actually be our full selves. The reality is that no one has it all figured out, and the way to be with that is to have communities where that is normalized rather than continuing to trudge through the mud of stuckness, pretending that everything is nice and dandy.

It'd be digital-first to be location-agnostic with in-person retreats 2-3 times a year to foster genuine connection. It'd be membership-based so everyone is fully committed, can financially sustain their participation, and so that it can stay small. The pitfall of many online communities is that they get too big (often because they are free), and people stop engaging.

There'd likely be other coaches in the community but it wouldn't be a community of solely coaches. There'd be plenty of people who have gone on sabbatical before, but it wouldn't be purely about career transitions. If being on sabbatical is about passivity, rest, unlearning, etc., then this would be more like post-sabbatical, where there's often greater sense of direction, ambition, energy, but still lots of uncertainty.

There'd be entrepreneurial people, but it wouldn't be another founder community (which would be unnecessary; I'm only interested in creating what I feel is truly needed in today’s world). It would include multidimensional people with a wide range of interests, perhaps people who view themselves, or are inspired by, the convergence of entrepreneur, athlete, and artist. These are people questioning the status quo—not just thinking differently, but actually living differently.

AI Coach Copilot

As a coach who studied computer science and worked in tech, I've been paying attention to the proliferation of AI coaching and therapy. Therapy/companionship is now the #1 use case for generative AI, a development that’s equally exciting and frightening.

I think the discourse on whether AI will replace human coaches and therapists lacks nuance, which I'm guessing is how it is for other fields like coding, design, writing, etc. My general take is that AI therapy will outperform mediocre human therapists in areas that are primarily thought-based, cognitive, and grounded in logical reasoning. While these rational approaches represent a decent chunk of therapeutic work, they miss crucial dimensions of healing that involve embodied experience, relational attunement, somatic awareness, and emotional processing that occurs beyond conscious cognition. Human practitioners create resonant connections, read subtle nonverbal cues, and facilitate healing through presence itself, things that AI can’t replicate (yet).

I predict more and more people will use AI for therapy, necessitating a more nuanced taxonomy of therapeutic approaches. We may need terminology that distinguishes between 'cognitive-algorithmic support' (where AI excels), 'human-facilitated integration' (blending AI insights with human wisdom), and 'embodied transformation' (requiring human presence). These conceptual distinctions would help clients understand which modality best serves their specific needs at different stages of their healing journey.

Rather than view it as a black-and-white either/or situation, I've been exploring what it would look like to augment human coaches and therapists with AI. If I look at my own coaching practice as an example, I see most of my clients only twice a month. That means that on average, they don't see me for 28 out of 30 days, which is a lot. I also know that even though I offer unlimited async communication, some of my clients are using ChatGPT as their therapist or coach because it's always-on and freely available.

What I envision is an AI that's trained on an individual human coach's approach and communication style. It could understand the practitioner's training methodology even more comprehensively than they can themselves while maintaining the individual's voice. Clients would use it in-between regular sessions, and the coach could receive a summary of each AI interaction to stay informed. If situations escalated or deeper processing was needed, the AI could notify the human coach.

In practice, I could have MattBot which existing clients can use, but it could also serve as lead generation. I've already seen one case of this, which judging by the UI seems like it's a custom GPT. I could see myself building something similar.

Lifty: Runna For Weightlifting

Runna, a personalized running coaching app, was recently acquired by Strava, and I believe the weightlifting community needs an equivalent. Unlike running, where progress follows relatively linear patterns, weightlifting demands complex programming that balances progression, recovery, and exercise selection. Most lifters plateau not from lack of effort but from suboptimal programming.

This insight crystallized after reading the HBR report highlighting therapy as the #1 use case for LLMs. While human psychology presents overwhelming complexity for AI, fitness exists in a more quantifiable domain with clearer causality. Physical adaptation follows predictable patterns that AI can model effectively, making weightlifting an ideal candidate for intelligent programming.

Current fitness wearables like Whoop and Oura Ring operate on a machine-measures-human-decides model, providing recovery scores that users must interpret themselves. I'm proposing the inverse: a system where humans report subjective metrics like fatigue and RPE, while AI handles the complex decision-making of programming adjustments. This approach flips the traditional relationship to leverage both human perception and machine intelligence at what each does best.

I've tested this concept personally with Claude, creating a custom prompt that generated a comprehensive 12-week strength program tailored to my preferences. By outsourcing programming decisions, I escaped my tendency to repeat familiar workouts and underestimate my capabilities. The freedom from constantly how much to lift has lightened my mental load (pun intended). Now, I simply execute the plan (lift the weights) and consult Claude for the occasional adjustment.

An initial version of Lifty could feature a simple UI collecting user inputs about equipment access, training history, and goals. The core value would be the AI engine that not only creates the initial plan but continuously refines it based on performance feedback. The real magic happens when the system learns your individual response patterns to different training stimuli and optimizes accordingly. Social features allowing users to tag equipment, supplements, and goals would create valuable network effects and dataset enrichment.

I want to make this, so if you want to collab, hit me up!

AI Mediator For When Couples Are Fighting

When things get heated between two people, it can be hard to take a step back and breathe deeply enough to address the conflict with greater consciousness. In those moments, we often say things we don't mean and forget our communication tools.

I believe there's an opportunity for an AI to mediate arguments between couples in real time. Imagine a voice-based app that couples could use together during conflicts. It would prompt each person to slow down, listen more effectively, and engage thoughtfully. The AI would listen to both sides and ask questions using principles from Crucial Conversations, Conscious Loving, and Non-Violent Communication. Since it can identify different speakers, it would guide each person through the process while maintaining neutrality.

The practical challenge is implementation. You can't really pause a heated argument to download an app from the store. Perhaps couples could install it during peaceful moments, after discussing how they want to improve their conflict resolution. But I wonder how your partner would react if you suddenly said, "Hey, let's keep fighting, but with this AI app listening to us." That conversation itself might require its own mediator.

While this idea needs some refining, I still believe using powerful technology to facilitate healthier human relationships holds real promise. Instead of technology pulling us apart, it could actually help us become more present, understanding, and connected with each other.

Guided Meditation For Fitness Enthusiasts

I've been thinking about creating guided audio specifically designed for fitness enthusiasts that focuses on inner shifts while in motion, rather than traditional seated meditation. This would target four key moments in a fitness enthusiast's day: morning, pre-workout, post-workout, and evening.

The pre-workout audio would focus on energy activation, mental preparation, and readiness, helping athletes get into the optimal state for performance. These sessions might incorporate visualization techniques, power phrases, and specialized breathing patterns to heighten alertness and sharpen focus.

Post-workout audio would guide listeners through recovery, calming the nervous system, and promoting down-regulation. It would feature breathwork designed to shift from sympathetic to parasympathetic states and guided body scans to release tension from worked muscles.

I've seen fascinating research on how specific audio interventions can help our bodies recover faster after tough workouts. When we intentionally downshift with calming sounds and guidance, our bodies actually process stress hormones more efficiently and transition to rest mode more quickly. The morning and evening sessions would bookend the day with intention-setting and reflection, creating a complete gym-for-your-mind that complements physical workouts.

This concept builds on the mind-body connection. Unlike traditional meditation apps that separate mental practice from physical movement, this approach integrates them. This could appeal to an entirely different demographic that finds traditional meditation unappealing but readily embraces mental training that fits within their existing fitness routines. It’s like a trojan horse to mindfulness for people who identify as doers rather than sitters.

Senior Caregiving x House Crisis

Ever since I was five, my maternal grandparents have lived with us. Now that they’re both 90, I’ve been witnessing their aging and the challenges that come with accessing proper care. This led me to look into the caregiving industry and understand what options exist for aging Americans who want to stay in their homes rather than move to nursing facilities. What I've discovered is that in-home caregiving businesses are essentially betting that institutional care options won't be able to meet the demand as 73 million baby boomers continue aging into their elderly years. Most older Americans are sitting on their biggest asset (their home) which often has multiple empty bedrooms now that their children have moved out decades ago. Meanwhile, younger generations can't afford to buy homes, with the median homebuyer now 56 years old and first-time buyers accounting for just 24% of purchases2. Additionally, the senior caregiving industry is dominated by franchised agencies with little technological innovation beyond Honor’s efforts.

Here's my moonshot idea: A system where younger people who can't afford today's housing market move in with elderly homeowners, providing caregiving while living in those empty bedrooms, and eventually purchase the home under favorable terms when the owner passes away through mechanisms similar to seller-based financing. It's a wild idea that would require new legal frameworks, but it addresses both the "gray tsunami" and the housing crisis simultaneously.

Maybe the simpler approach would be facilitating more intergenerational living, which is already common throughout most of the world. It just seems somewhat obvious that if you have a growing population of (relatively) wealthy old people who need assistance and a challenging housing market for young people, you could address both problems by creating structured connections between these groups.

Ski Hacker House

I'm envisioning a Ski Haus 2.0 concept for next winter: a month-long co-living experiment in Salt Lake City during peak snowfall (mid-Jan to mid-Feb). Despite the name, this isn't exclusively for programmers but for multidimensional people who are passionate about both their work and having a good time. The house would foster an intentional community where participants can weave together business and daily mountain pleasure, offering an integrative alternative to the conventional work-life divide that dominates our culture.

To strike a balance between shredding pow and clickity-clacking on laptops, the daily rhythm might look like:

• 7:00AM: Wake up

• 8:00AM: Out the door, mountain bound

• 9:00AM - 12:00PM: Skiing

• 12:00 - 1:00PM: Driving home + shower + lunch

• 1:00 PM - 10:00 PM: Working with a dinner break

Last season was awesome, but lacked synchronization among ourselves. We basically all did our own thing and then skied together when it was convenient. This more structured approach would hopefully lead to more generative chairlift conversations followed by collaborative work sessions around a communal table.

At a meta level, this experiment explores what it looks like to design lives that flow with natural rhythms rather than fighting against them, integrate work with lifestyle rather than pitting them against one another, and create temporary "pop-up" intentional communities rather than permanent social structures.

Let me know if you’re interested—I’ll probably start putting this in motion in late June/early July.

Some Questions I’ve Been Thinking About

What are you going to do now that you have a shit ton of money?

Just purely based on anecdotes from people I know, there are likely thousands of people living in the Bay Area between their mid-30s and 40s who have a net worth of $5M+ who still think they need to work full-time jobs. In some cases, it’s because they’re on the hedonic treadmill and sitting with a monthly burn rate that includes a hefty mortgage and expensive childcare, but there’s plenty of other cases where they’re financially free yet continue working. Even if they have kids, they don’t know what to do with their time during the day. It’s a chicken-and-egg problem. If all their friends who are in similar situations stepped off the full-time work path, they could band together and make cool projects instead.

Why do we suffer from both comfort crisis and hustle culture?

We are currently living through a profound contradiction. We experience unprecedented comfort alongside epidemic despair. While drowning in excess calories, infinite digital stimulation, and material clutter, we simultaneously buckle under chronic stress, caffeine-fueled overwork, and widespread burnout. This paradox explains why Jung described a third of his patients as those who lacked a diagnosable clinical illness, but simply suffered from “the senselessness and emptiness of their lives”. As studies confirm rising rates of depression and anxiety during the safest, most prosperous era in history, we face the ultimate modern challenge: learning when to embrace struggle rather than flee it. The path forward requires discernment, knowing when to stop consuming, recognizing how much is enough, and developing the capacity to sit with ourselves undistracted. I’m personally addressing this question by doing hard things like working out and moving my body in nature, while limiting exposure to brainrot internet content.

Man has achieved his present position by being the most aggressive and enterprising creature on earth. And now he has created a comfortable civilization, he faces an unexpected problem... The comfortable life lowers man's resistance, so that he sinks into an unheroic sloth... The comfortable life causes spiritual decay.
- Colin Wilson [source]

Why are young-ish people not looking for love?

It's a tragedy that so many people in their late-20s to 30s want a life partner, but aren't actually prioritizing that search in their lives. This is a multilayered issue: unrealistic expectations from social media, surface-level dating app interactions, fear of approaching people, fewer social venues, and struggles with intimacy.

But I think our relationship with work is the biggest problem. There's nothing wrong with working hard. The issue is how much meaning we assign to our jobs. When most of our life's meaning comes from work, we try squeezing more fulfillment from our 9-5 by working longer hours and chasing promotions, when sharing life with someone we love would actually bring far greater happiness.

I’m observing this problem so often that—who knows—maybe I’ll make dating a more explicit part of my coaching. As someone who spent my first 26 years single while chasing mountain peaks and corporate ladders, I've had to learn to make space for partnership. Nothing replaces the stoke of surfing at sunset, but a warm hug with someone you love is also pretty great. My unsolicited advice (only saying this because it's my blog and you've read this far) is to make room for both 😊.

Stuff I Like

Here are a few creations that I resonated with recently:

• A beautiful metaphor for what it looks and feels like to be in transition by : What happens when you leave your career (and identity) behind

• A raw and honest take on the importance of how you navigate transition: Destabilization & the Frequency of Values by

• A provocative and soulful conversation that resonated deeply as I listened to it while walking outside during sunset: Martha Beck on the EvolutionFM podcast by

If you’ve made it this far, thanks for reading! Let me know your thoughts, questions, and feedback in the comments!

The Journey to This Point

My actual sabbatical took place in 2023, but it feels like I'm on sabbatical again. The only other time I felt this way was in spring 2019 during the liminal space between having graduated but not yet having started my first job. In 2019, with the security of a job lined up, the time wealth of an empty semester, but also a somewhat empty wallet, I ventured outwards to see the world. As I visited China, Taiwan, Peru, Patagonia, and Indonesia, there was a desire to seek, understand, and immerse myself in experience.

After a yearlong sabbatical, I ventured into the world of coaching. It's hard to pinpoint exactly when I knew coaching was the path I wanted to be on. I don't think I ever knew, so maybe hoped is a better word? The reality was that cold hard facts and lack of evidence should've deterred me, but curiosity pulled me forward because it was as exciting as the first time I put a blindfold on trying to hit a piñata at a birthday party or when I tried to paddle for my first wave. I was so fervently focused on learning about coaching everyday that the inability to see where this path would lead disappeared from my awareness. In other words, at some point, I stopped worrying about the future.

As I danced with uncertainty and eventually stumbled into coaching, I never once sat down to write a business plan for how this new venture would fully sustain my lifestyle. I'm actually glad I didn't because it was my youthful naiveté that allowed me to continue down a path that many don't dare to explore until much later in life. The same naiveté, however, meant that I gave little thought to my financial future. I simply assumed that coaching meant being a solopreneur with my own business.

Fast forward 18 months to today and a lot has happened. I've completed an apprenticeship, started my own coaching practice, and also begun training in somatic psychotherapy. I'm proud of the progress I've made, yet also aware of the practical desires I have. I'm currently earning enough to cover living expenses with a tiny bit leftover for savings, and that feels pretty good considering I started my own practice less than a year ago. But it also doesn't feel like enough to be completely comfortable and that results in a complex blend of emotions.

Making the Decision to Recalibrate

I feel excited about where my coaching practice is headed, but I also worry about money. There's a sense of satisfaction with my coaching practice and a dissatisfaction with my coaching business. I think it's better to be brutally honest with myself and take the nail out of my head2 rather than parade around in a mirage of delusion. But the quality of the dissatisfaction comes along with acceptance and surrender. It's like being in a kayak. I must flow with the river while remembering to paddle intensely at times3. I think it's okay to not be okay with certain aspects of life as long as that's met with a sense of agency and trust (in oneself and the universe/choose-your-god). Sugarcoating problems only leads to avoidance.

My original plan was to wait until I had a new gig figured out to share the news. But as I kept pressing down on the gas pedal, it felt like I was fighting gravity in a vacuum chamber of compressed time. As I turned inwards and felt the resistance, I uncovered subtle layers of shame and sadness. I worried about being perceived as if I'm quitting or failing. I’d often oscillate between blindly hoping for a miracle or telling myself I needed to lock in, turn to growth hacks, and sell sell sell. I’m aware that it’s a false dichotomy, but I just felt something needed to change. The financial reality is undeniable. I haven't generated the income I need to sustain my lifestyle long-term.

As I've unpacked this, I've come to see how I was projecting other people's opinions onto myself. After all, aren't we all looking for a great story? The story of the underdog who surmounted great odds or the boy who left home on a grand mission and returned as a hero. Whether I like it or not, the storyline can only be seen in hindsight. In the present moment, it's messy, ambiguous, and unpredictable.

Approaching the Search Differently

So this time around, I'm really letting myself freely wander. I've been having many conversations with friends, former colleagues, and total strangers, with topics ranging from AI therapy to agentic coding to transformational communities. At first, I approached each specific topic or opportunity with a narrow self-presumed role like product manager or coach. When I felt like I had to choose a partial identity to present myself with, I felt like I was wearing a mask, which led to frustration at both myself and the other person for me not feeling fully seen. It's an ongoing process, but I'm learning to show up as my full, whole self which is daunting, but also essential.

Dropping seemingly unrelated little bits of myself in conversations has led to some unexpected twists and turns. For example, I mentioned to a recruiter that I was learning about the senior caregiving industry and then she told me about how her mom used to be a hospice worker and since her dad traveled often for work, as a little girl she'd go with her mom on late night visits to patients. Even though she focuses on recruiting in the tech industry, we ended up talking about skiing and coaching too. This openness creates authentic connections that transcend transactional networking.

This period has also helped me reconnect with my intellectual curiosity for how to solve big problems with tech. When I step back and look at my arc for the past few years, I spent my early career in tech, but without many human skills. Since leaving the tech industry, I've been more focused on what it means to be human, both from a personal perspective, and also in my coaching work, which is human-to-human with minimal tech. The next chapter of my career is about integrating scalable problem-solving with deeply human, relational work.

In my free time, I've been learning about AI and heavily using tools like Claude, Perplexity, and Lovable. What's most fascinating is the speed at which all of this is happening. When I was an EECS student at Berkeley, I enjoyed learning computer science as theory, but could never get myself to enjoy coding because of how frustrating it was to debug and meticulously ensure there were no syntax errors. So much of what kept me from pursuing a career in programming has now been abstracted away by AI. The gap between idea and creation is only getting smaller, and that excites me as someone who has a lot of ideas, but not a ton of patience for getting every little detail figured out. The rapid change we’re seeing now in technology, politics, and the economy align with my personal evolution. As the world increases in chaos and complexity, I’m intentionally positioning myself to be adaptable, resilient, and agile.

Navigating Uncertainty Mindfully

Wading in the knee-deep murky waters of uncertainty is still challenging despite my familiarity with the unknown. With my Enneagram 6 and 8 personality, I instinctively believe I can control outcomes through sheer willpower and grinding harder, but that approach consistently fails me. What actually works is opening myself to possibility through concrete actions: asking for help, reconnecting with people, and documenting unexpected opportunities as evidence that my predetermined plans rarely manifest as expected. When I first entered this transition, I reflexively set deadlines and timelines, trying to minimize uncertainty just as humans have evolved to do. But the complexity of finding meaningful work in 2025 defies this caveman-like approach to problem-solving. Instead of fighting this reality, I'm accepting that I'm not fully in control while maintaining forward motion through an easeful yet deliberate pace. Rather than letting stress and fear propel me, I'm anchoring myself in the deeper meaning and purpose behind my endeavors.

At the start of my search, I caught myself replaying a past pattern of making the job search more stressful than it needs to be. I’ve only had to look for a job twice. The first time was during senior year of college when I was dealing with betrayal that resulted in me wanting to graduate college ASAP with something to show for. The only other time was during the peak of the pandemic after I got laid off with less than a full year of experience. With the awareness that this time doesn't need to be like the past, I’ve begun to look at this next chapter with fewer assumptions. Instead of being default driven by anxiety, I’ve taken a step back and recognized this period for what it actually is: a blank canvas opportunity to find meaningful work that supports me while allowing me to contribute with my unique strengths and skills.

Money and Meaning: A New Relationship

It's hard to explain what I'm going through right now. I'm not winding down a failed startup or quitting a passion project. What I'm experiencing isn't so much a transition as a recalibration. I'm releasing the pressure to earn a full-time income from coaching, but the practice and it’s meaning in my life continues uninterrupted. I'm intentionally choosing to create space between money and meaning.

This separation feels like a necessary step in the evolution of my practice. By creating distance between the practice itself and financial constraints, I’m creating room for growth. I get inspired just thinking about what might emerge given a few years to incubate, develop, and nurture my practice in a conducive environment. I’m focusing on the present situation, but I have a clear vision for where I’d like to steer towards, in terms of work and how I want my life to be.

It's also strange because I sort of did it out of order. Usually people start to explore ideas and tinker with experiments when they're still employed. With the stability of a job, they spend their nights and weekends bringing something to life and seeing if it "has legs". My friend who's a full-time content creator was posting TikTok videos for over a year before quitting his job. Other friends who have started their own companies don't leave their jobs until they've secured funding.

In my case, with the benefit of hindsight, I don't actually see how that could've been possible for me. It's almost like I had to leave full-time work for two years in order to get to where I am now. I was carrying a heavy backpack of frustration, confusion, and hopelessness, a burden that only began to lighten once I stepped away and consciously set it down. Towards the end, I internalized resentment towards other people and the company. It took time and space to unwind that and realize that all the negative emotions I was experiencing were self-created. With this newfound clarity, I've come to appreciate everything that I had in my previous jobs while also accepting that it was the right time to leave.

By seeing how I was the creator of my mental prison, I've been able to own what's mine and absolve the externalities from blame. There's nothing inherently wrong with working a full-time job or being a product manager. Having walked this path myself, I now understand what it takes to navigate similar terrain. This firsthand experience is essential, as there's no other way to guide people in the wilderness without having spent time in the wilderness yourself.

At its core, what I’m going through right now reflects what I see so often in others. We think it’s the job we work, partner we date, boss we report to, or city we live in. But it’s so often not just the external thing that is creating the problem. It’s how it’s paired in combination with the inner conflict. That’s why when we actually get what we want, whether it’s the addition of something new or the removal of some existing thing, it rarely feels as good as we imagined. That’s because the essence of what we actually want is a feeling of safety, security, belonging, and freedom. It gets down to our beingness4, the quality of our present experience. And that’s something I’ve had to remind myself over and over again during this period.

The Beauty in Uncertainty

With the speed of modern society, it can often feel like we need to approach liminal spaces with a specific objective and timeline, but from the past month, this strategy has only led to urgent grasping and unnecessary suffering. I'm learning that this recalibration isn't about failure, it's about adjusting course on an uncharted journey. The path I sought with coaching looks different than expected, but that's okay.

Staying on the path means being brutally honest with myself about what is actually not working while also not shaming myself or sulking in gloom about it. I'm creating space between money and meaning, not because there's anything wrong with trying to monetize meaningful work, but because forcing it has created friction that doesn't serve me. By allowing some separation between financial demands and my coaching practice, this craft I intend to practice for decades has room to evolve naturally.

What I'm discovering is that coaching skills aren't confined to formal sessions. It's a way of being I can bring into any workplace or conversation. This integration of tech knowledge with human understanding feels increasingly important in a world where these domains are often separate.

As I continue my search, I'm focusing on contribution rather than urgency. What can I offer? How can I serve? These questions feel more authentic than anxious timelines or expectations. The uncertainty is still there, but so is the possibility.

For me, this isn’t about escaping discomfort. It's like hiking a challenging trail where I've accepted the blisters and unpredictable weather as part of the experience. Some moments I'm catching my breath, other times I'm standing in awe at a vista I never expected to find. I still feel the uncertainty of what lies ahead, but there's also a strange sense of beauty in the depth and richness of seeking something new. I'm learning to trust my footing even when the path isn't clear. Coaching has evolved from a casual walk to a never-ending adventure, challenging and rewarding in ways I couldn't have imagined. The mystery is the invitation, the rawness is the teacher, and the wonder comes from embracing both.

At this point, it's abundantly clear that I'm going through a transition. In the past, transitions were really hard for me. New difficult emotions would arise and I wouldn't know how to process them or be with them. Now I still experience anxiety and worry about the future, but I notice these feelings much sooner. Instead of weeks of anxiety, it's now more like two days, followed by an "oh shit" realization which usually involves a difficult conversation I've been putting off or reeling back from trying to do too much.

This transition, whether by nature of being shorter in duration, or because I am far more prepared to navigate it now, feels more like a micro-transition. Quitting my job took me over ten months, my sabbatical lasted a year, and it took me six months to actually start my coaching practice. This shift isn’t as big of a deal as going on sabbatical or starting to coach; there's far more continuity and integration going on right now and it’s happening within a larger movement between life phases.

The discomfort of transition stems from newness itself. I observe this pattern repeatedly. The high-achiever granted freedom to pursue anything becomes paralyzed by possibility. The successful founder post-exit writhes with internal conflict when refusing investment opportunities and networking calls that no longer resonate. Clinging to old identities keeps us playing games we've outgrown, while speedrunning to escape discomfort only perpetuates it. The only way forward is to sit—patiently inhabiting the mysterious fog that will clear in its own time, according to its own wisdom. I'm getting better at sitting in this fog now, with more tools than I had in previous transitions.

Seasons of A Man’s Life

I'm becoming increasingly aware of which season I'm in—the phase right before settling down. It carries a distinct feeling of urgency, purpose, and motivation. There's pressure, but it's not entirely unwanted; it feels like a natural progression.

My internal assessment aligns with psychologist Daniel Levinson's work in The Seasons of a Man's Life. His research team at Yale interviewed 40 men across different walks of life and identified throughlines in their stories, developing a theory of the "life cycle and its seasons." I'm particularly drawn to two phases: "Entering the Adult World" (ages 22-28) and "The Age 30 Transition." While the book was published in 1978, and the exact age ranges have likely shifted with people marrying and starting families later, the core principles have withstood the test of time.

In exploring Levinson's work on life seasons, I'm struck by how he nails the fundamental conflict guys like me face in our twenties. We're caught between wanting to keep our options wide open while simultaneously feeling the pull to build something meaningful and take on grown-up responsibilities.

As we edge toward our late twenties, there's this growing awareness that the window for major life changes is starting to narrow. This creates the urgency that defines the whole Age Thirty Transition. We start seriously questioning our current path—career, location, relationships—realizing that decisions we make now will shape decades to come.

One of Levinson's spot-on insights is that life forces us to make huge decisions before we're actually ready for them. He writes, "One of the great paradoxes of human development is that we are required to make crucial choices before we have the knowledge, judgment, and self-understanding to choose wisely. Yet if we put off these choices until we truly feel ready, the delay may produce other, greater costs."

Moving into our early thirties, the main task becomes commitment—narrowing our focus to go all-in on what truly matters. The scattered exploration of our twenties gives way to building something substantial in our work, relationships, and community.

What resonates most with me is Levinson's concept of "the Dream"—that personal vision guiding our life choices. This concept beautifully complements what Joseph Campbell explores in "The Power of Myth," where he shows how myths aren't just ancient stories but living frameworks that help us understand our place in the world. Like Campbell's hero's journey, Levinson's Dream serves as our personal mythology, the story we tell ourselves about who we are and what we're here to do.

It's taken me nearly four years to get clear on my own vision. Looking around, I notice many friends still don't have this north star. Back in 2021, my supposed vision involved living nomadically in a van with a partner and maybe a dog. Looking back, this wasn't actually about my future—it was about wanting freedom and adventure within a relationship at that specific moment in time.

Levinson beautifully describes this concept: "A man's Dream is his personal myth, an imagined drama in which he is the central character, a would-be hero engaged in a noble quest." He quotes Goethe's insight that "For a man to achieve all that is demanded of him, he must regard himself as greater than he is."

One of the biggest challenges I've found with developing this Dream is finding the sweet spot between commitment and flexibility. I need a vision strong enough to organize my life around, but holding it too rigidly leads to disappointment and missed opportunities. The challenge is to create a Dream with enough structure to guide myself while leaving room for it to evolve as I do. It's less about executing a fixed plan and more about following a living, breathing vision that remains open to life's unexpected turns.

The stakes of this transition are surprisingly high. A failed transition can mess you up, as you might struggle to see meaning in life beyond this point. On the flip side, as Levinson notes, "Those who build a life structure around the Dream in early adulthood have a better chance for personal fulfillment, though years of struggle may be required to maintain the commitment and work toward its realization."

What makes the Age 30 Transition so pivotal is that it represents a "second chance" to create a life that actually works for you. There's both opportunity and urgency—a recognition that while change is still possible, the window is closing. The carefree vibes of our twenties are ending, and life is becoming more consequential. As Levinson says, by age 30, there’s "a stronger sense of urgency to 'get serious,' to be responsible, to decide what is truly important and shape his life accordingly."

I'm learning to balance these opposing forces. Taking my life choices more seriously while refusing to sacrifice playfulness and wonder. When I make decisions now, I'm not just asking "Is this responsible?" but also "Will this keep me curious and energized?" I'm navigating the challenging leap from big kid to serious adult while fiercely protecting that sense of childlike joy and wonder that makes everything worthwhile.

On Change and Transformation

I've been noticing subtle but significant shifts in myself lately that align perfectly with what Levinson describes. My once-insatiable appetite for travel has mellowed. Instead of constantly searching for the next adventure, I find myself craving routine and stability—a predictable rhythm to my days that allows for deeper work and more meaningful connection.

What's interesting is how good it feels to embrace the role of the seeker again. Being in pursuit of something carries a certain energizing quality. There's a youthful vitality to actively working toward change and growth, whether in the gym or in my career. The state of being in pursuit feels deeply natural, almost primal. We were born to be in pursuit of something.

This pursuit creates an interesting tension with the Buddhist principles I've been exploring. On one hand, Buddhism teaches acceptance and non-attachment to desires. On the other, having direction and purpose feels essential to a meaningful life. I'm learning that these seemingly opposing forces can coexist—the challenge is discerning which desires are genuine expressions of my deeper self versus those I've absorbed from others or society.

Western individualism conditions us to reject others' expectations as inherently constraining, but I'm finding that sometimes wisdom comes from listening to what people or our environments are telling us. The real skill isn't blindly following my desires nor ignoring them completely—it's developing the discernment to know which ones merit attention and commitment.

As I lean into this season of commitment and clarity, I'm reminded of another Campbell idea that keeps coming back to me: "We must be willing to let go of the life we planned so as to have the life that is waiting for us." The Age Thirty Transition isn't about figuring everything out once and for all—it's about developing the courage to commit to a path worth walking while maintaining the wisdom to adjust course when necessary.

Other Musings

Tending To A Garden of Relationships

Being back in NYC, specifically the Upper West Side for the next month, has reminded me just how important relationships are. I've been reconnecting with people and realizing that I actually have a lot of genuine, real connections here.

I've developed an interesting pattern from my years without a lease—I'm always the one who reaches out first, and it works. While many people hesitate to contact friends (not wanting to be a burden or fearing rejection), I've never struggled with this. Since I'm constantly on the move, people don't know where I am, so they expect me to initiate. This structural dynamic makes the "uneven" reaching out feel completely natural.

It's been rewarding to not only reconnect but also to experience the reciprocity of help from people I've supported in the past. I'm starting to appreciate just how long life is and how many re-encounters we have with people, even after one chapter ends.

Morning Rituals That Ground Me

I've settled into a morning routine that helps me start each day with clarity: stretching → meditation → walking around the reservoir → decaf coffee + one page of morning pages.

I've noticed that meditating after some movement allows me to drop deeper than if I were to start meditating immediately. There's something about getting embodied first through physical movement that creates a noticeably different meditation experience.

The reservoir loop in Central Park has become a special place—the one-way path means everyone moves in the same direction, creating a peaceful flow without the need to navigate oncoming traffic. It's meditative in its simplicity.

I've intentionally scaled back my morning pages to just one page instead of two—a practical trade-off that keeps my morning routine from consuming two hours. For ad-hoc reflection, I've been using Lightpage for voice journaling during walks, which has been a game-changer.

Questions I'm Sitting With

As I navigate this transition, several questions keep surfacing:

• What would it look like to integrate the human work I do in coaching with technology work?

• As an Enneagram 6 who struggles with self-trust and anxiously tries to forecast the future, how can I navigate this next chapter with more openness and patience?

• What is my environment trying to tell me, and how can I act in accordance with that? (Whether "environment" means the universe, a higher power, or simply what I observe outside myself that resonates)

• How do I balance enjoyment and work? Rather than seeking ways to work less and play more, I'm curious about how to enjoy the process of working—integrating play and work in a way that isn't common but feels right for me.

These questions keep me company during this seasonal shift. I feel the pressure of decisions that will shape my coming decade, yet find satisfaction in finally committing after years of keeping options open. Understanding these life seasons helps me see this not as random anxiety but as natural development. The uncertainty remains, but I'm learning to see it as a companion rather than an enemy. This balancing act and intentional shift embodies the essence of navigating life's seasons.

When COVID derailed my plans in NYC in 2020, the disruption sparked an unexpected opportunity. With remote work suddenly normalized, I found myself with unprecedented freedom to reimagine where and how I lived. After landing a new job following a layoff, I left the Bay for Utah and Colorado, drawn to wide open mountain landscapes when the world felt increasingly confined. What started as a pragmatic escape has transformed into a seasonal rhythm attuned to both nature's cycles and my evolving desires.

My friend Parker and I didn’t know what we were doing and that was okay. We Airbnb’d a condo in Frisco, Colorado and invited every snow-obsessed friend we knew. At any given point we had anywhere from 4 to 12 dudes crashing at our three bedroom mountain condo. This was when I discovered the magic of skiing on weekdays. Without lines, I could ski from first chair until noon and feel like I had gotten a weekend’s worth of runs. My work schedule fit perfectly around my powder pursuits and I’d come home and work until 8 or 9pm. Coming from weekend warrior mode, this way of living felt like a luxurious life hack for a frugal young dude.

The next year I went all in. I spent most of the season staying with a local in Incline Village in Tahoe, but I also skied triple blacks at Big Sky, flopped into Corbet’s Colouir at Jackson Hole, drowned myself in pow at Aspen, and ripped at the Utah resorts too. I remember ending that season in April 2022 with some shirtless spring slush skiing at Palisades and completing a 72-mile bike ride around Lake Tahoe. I had racked up over 60 days of skiing and there were no signs of slowing down.

The 2023 ski season coincided with the start of my sabbatical and the first time I joined a ski lease. As I began going inwards more and diving headfirst into my climate newsletter and podcast projects, I experienced a type of tension for the first time. I was facing choices between multiple things that I wanted to do. In the past, skiing in the morning and then working into the night was the default because I could fit everything I wanted and needed to do into one day. The pursuit of flow pulled me while the desire to escape an unfulfilling job pushed me to be outside. I was having to choose between skiing and my own creative work that I was doing with no financial incentives. With total freedom in how to structure my days, it wasn’t as simple as trying to maximize ski days.

2024 was a continuation of this emergent understanding that I no longer needed to ski as much as possible, even when in a position to do so. The dilemma I felt between heading to the mountains or staying in to read an enthralling book was weird for me. It felt foreign to have other passions and pursuits that demanded my attention. I still enjoyed skiing, but now it was clear that I needed to make room for other things in life. I was transitioning from nomadic ski bum with an unquenchable thirst for snow to perhaps a wiser version of myself who recognizes that just because you love something, doesn’t mean you have to be immersed in it 24/7.

Looking back, I see how the pandemic had not only accelerated remote work and online learning, but also chapters of my life. I went through distinct phases where my relationship with skiing rapidly evolved. I was experiencing the phenomenon that all of our desires have finite time windows. There was a time when I wanted to ski as many days as possible. And just like the appeal of staying in hostels, that time has passed. Viewing our biggest dreams as temporal and time-bound can be disorienting because things are constantly in flux, but it can also be quite peaceful. By acknowledging that not everything needs to remain as is, I open myself up to the Buddhist concept of impermanence, the notion that everything is subject to constant change, decay, and eventually, cessation. It’s similar to Bill Perkin’s idea of “mini-deaths” in his book Die with Zero, as well as the film Past Lives. There’s a beauty in noticing the change. It allows us to attune to our desires in the present moment and act accordingly, appreciating that they may not always be with us.

That is what I mean when I say that we die many deaths in the course of our lives: The teenager in you dies, the college student in you dies, the single unattached you dies, the version of you that's a parent of an infant dies, and so on. Once each of these mini-deaths occurs, there's no going back.
- Bill Perkins

Salt Lake City 2025

After two years of joining ski leases others had organized in Tahoe, I decided to create my own version this year. I knew this might be one of my final seasons of living this way, so I wanted more agency in all aspects—from location to space to people. After skiing all over the west (and not even considering the east for obvious icy reasons), I landed on Salt Lake City, the ideal blend of great skiing, comfortable convenience, and affordable housing.

Perhaps from breaking my ankle in early 2024, which cut my season short, I started to get the itch for skiing unusually early in June. I recruited my friend Niles who also lives without a lease and we began browsing for the ideal place to stay. After years of winter visits to Salt Lake City, I had a good sense of what we wanted: spacious yet proximate to the mountains, with TJs, Costco, and a gym not too far away. We committed early, before anyone else was even thinking about their next ski season, and we felt confident that if we “built it”, people would come.

Our Airbnb was nestled in Murray, a suburban town south of SLC that’s usually quiet, unless it’s a powder day. Then, a long “red snake” of cars forms, trying to make their way up Big or Little Cottonwood Canyon. With five bedrooms, two living rooms, a ping pong table, and a driveway big enough for seven cars, this spot was a great home base for the month. An eclectic bunch came from SF, LA, NYC, and Singapore, bringing along a diverse set of work situations, from not working at all to freelancing to self-employed to working a ton. Despite our differences, we all made our rooms feel as homey as possible and were united by skiing and snowboarding.

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Coliving + Skiing Together

My interest in living this way emerged from a broader curiosity about alternative lifestyles. I’ve watched countless hours of tiny house and vanlife tours on YouTube. I read Supernuclear, follow the charter city movement, and admire projects like Cabin, HF0, and Edge City. Each offers a unique vision of “the good life” with distinct philosophies, values, and norms.

While I’m interested in aspects of these projects, I’ve structured my seasonal way of living to be more aligned with nature and my hobbies. My ideal coliving setup is more like Benji’s House, the first surf house on the North Shore of Oahu, rather than spaces designed around intellectual movements, company-building, or permanent coliving. I feel like I can get my fill of idea-sharing and sense-making online, but the only way to merge skiing with community is in the physical realm.

The beauty of seasonal coliving is its rhythm—stability most of the year followed by a dedicated window for adventure. As winter approaches, spending the dark months nestled in a labyrinth of skyscrapers becomes less appealing. Nature’s cycles become the focal point to anchor to. We convene when the snow gods start sprinkling across the mountains, and part ways when we’ve gotten our fill.

I suspect that many more people would prefer seasonal coliving over being fully nomadic or living permanently with others. Always being on the road gets tiring and finding the right configuration of people and place to cohabitate seems like quite the hurdle. Seasonal coliving sidesteps these constraints by bringing people together into a temporary shared space, co-creating in an intense burst before dispersing back to our respective homes, pockets filled with memories.

On the surface, it really is as simple as getting an Airbnb with friends, but the nuances come from the distinction between living versus vacationing. The monthlong duration afforded us the time to not rush, impacting how we bought groceries, decided when to ski, and our interactions. Each person’s independence was evident in our completely different wake-up times and morning routines. It was nice to do our own thing, but in a sense, together. The individual freedom was contrasted by the collective chaos in coordinating rides up to the mountain on weekends strategically balancing parking passes, road conditions, and skier ability.

By evening, the dilemma of dancing between skiing and working had usually subsided which allowed for more mingling. With the fireplace on and a cozy playlist, we’d share stories while Theragunning and doing our respective stretching and physical therapy. I enjoyed the contrast between the ambitious mornings, directed either at work or on the mountain, and the slower evenings, rotating through TV, puzzles, board games, reading, ping pong, and hot yoga.

The structure of the Ski Haus struck the right balance between individual and collective. It was the oscillation between hermit mode in my room with my keyboard battle station and running around the house trying to find people to hang out with that felt just right.

By the end of the month, it felt like the right time to complete this snowy coliving experiment. One by one, we packed our duffel bags and loaded up our cars (or ski bags for those flying). It didn’t feel sad though, we knew that we would cross paths soon enough, and there was always next season.

Why This Matters To Me

Ski life has transformed from maximizing mountain days to something deeper—an exercise in agency itself. I view my relationship with skiing and how I’ve prioritized it every year as an expression of agency and creativity. The question I keep asking myself is: “Can I do what I want despite the constraints?”

In this case, the constraints are clear. Skiing costs money and can only be done near mountains. The challenge of finding a way to enjoy great skiing while keeping it affordable has become a game for me. I’m in pursuit of the essence—something that ski and surf bums like Yvonne Chouinard, Jimmy Chin, and William Finnegan embody. It’s not about how sick the aprés is or how luxurious the lodge looks. It’s about being immersed in the raw beauty of winter landscapes, bonding with fellow seekers, flowing in harmony between body and mountain, and rediscovering the childlike exhilaration that makes you feel truly alive.

This January reminded me of my childhood, with the Ski Haus resembling a dorm and the combined car rides and ski lifts mirroring the school bus. The common areas of our Airbnb served as gathering grounds to hang out, even for just a few minutes in between meetings. Traffic and chairlift rides provided ample time to debrief, strategize, and gossip. I rediscovered what it’s like to be a kid again—a quality becoming vital to preserve. The world is getting serious and my responsibilities are getting heavier. I have plenty of role models who exhibit exceptional levels of ambition, discipline, and wisdom. But one subtle quality consistent among them all is that they deeply enjoyed the process, which is why it’s my childlike qualities that I’m particularly keen to never lose sight of.

This is likely one of the last years I’ll live and ski this way. I’m 28, unmarried, and don’t have kids, but hopefully that will change soon—at least the age part. I feel like this is one of those rare opportunities where I’m actually deeply aware of which chapter of life I’m in and can shape it accordingly. I’m with one foot in the big kid chapter and the other in the “settling down” chapter.

I’ve told my story to enough older folks, often with kids, who remind me that it’s not possible for them to live this way anymore—and I wonder if that’s truly the case or if it’s a combination of logistical hurdles and changing desires. I suspect it’s a mix of both. Their tone is a blend of jealously, judgement, and encouragement. It’s sometimes hard for me to discern how much fun to have when I could be using my resources toward career advancement. My stance is that the wisest thing for a young person to do is to recognize their abundance of time and learn and meet great people, but also to make memories and have fun.

In the past, I consistently overvalued long hours and status symbols and undervalued wild adventures and unbounded exploration. Perhaps the sweet spot is what Joseph Campbell referred to as bliss: “Follow your bliss and the universe will open doors where there were only walls.” I’ve always been attracted to having fun outside and living the question of what is the good life. January at the Ski Haus feels like a natural expression of myself, validating another Campbell quote, “The privilege of a lifetime is being who you are.”

Looking Ahead

As I approach the end of six years living without a lease, I'm reflecting on what elements of this nomadic life deserve a permanent place in my future. Living seasonally has taught me to pay closer attention to my environment and act in accordance with what exists beyond me. Being in touch with the weather and my surroundings is not only good for practical planning, it also creates a connection with what philosopher David Abrams calls the “more than human world”.

There’s also a more inward element of being aware of what I want, developed simply by having to repeatedly choose where to live on shorter time scales. This ability to not only be aware of desires, but also act upon them, is something I want to continue to cultivate.

Lastly, there’s what I’ll call “functional creativity”. It’s less like fine art and more like making use of what resources I have despite constraints. Finding the right Airbnb across several parameters, creating a makeshift office in my room, and architecting my schedule to allow for skiing and work are some examples of this functional creativity.

Next season, I’d still like to do this again. A month in Salt Lake City skiing the surrounding six ski resorts offers the right balance between world-class skiing and comfortable living that can accommodate modern responsibilities. But maybe it’ll be time to revisit Jackson Hole after three years. Or I’ll simply chase the storms as they say.

The time window for this type of living is closing and I’ve made peace with that. I’m excited for this next phase of life, although the lines are blurry and the chapter beginnings and endings are fluid. If you’re younger or in a more independent chapter of life, I strongly encourage you to explore this. And by this, I’m not referring to skiing or even coliving. I’m talking about the process of figuring out how you want to live, and then doing whatever it takes to make it come to life.

We’re so engaged in doing things to achieve purposes of outer value that we forget the inner value, the rapture that is associated with being alive, is what it is all about.
- Joseph Campbell