Since my last update at the end of June, I’ve experienced a lot of movement in both my inner world and the world around me. So if writing is metabolizing life’s experiences, then I’ve been collecting things to digest for the past few months.
In July, I drove down to LA twice to see my grandma, who had been hospitalized for weeks. She was 90, and her health had been declining for several years. The last time I saw her, I drove down on a Thursday morning and came back Friday evening. The next morning, I was on a flight to Mexico City. She passed away shortly after we came back.
Mexico was vibrant, just like I remembered from 2018. It was my first real vacation since starting the new job. I had taken some PTO earlier during ski season, but those were just half-days, which made it hard to truly unplug. When I last visited in 2018, I was supposed to arrive two days before my friend Jon, so when my non-stop flight was overbooked, I volunteered to take a red-eye to Chicago first in exchange for $1,200 in United credit. For a college student sleeping in hostels, this was a great trade.
Well, times have changed. We stayed in modern Airbnbs with gyms and rooftop pools and ate at restaurants serving giant prawns and tiny chickens that hadn’t been plumped up with processed feed. Back home, neither of us has much time to watch TV, so we watched The Odyssey with Spanish subtitles. Every seat was taken, and we were the only foreigners. I saw couples, families, and a few solo watchers still in their work attire. Despite being in a different country, we could all connect over the same movie.
A couple weeks later, we took a quick trip to Tahoe, leaving the Bay at 6:40pm on a Friday. The next day, we hiked around Emerald Bay, rode some rental bikes to the beach, and then I swam to a wooden pole planted 30 yards away from the lakeshore. I wanted to climb it but the algae made it too slippery and there were some nails sticking out.
In August, my friend Geo and I backpacked the Eastern Sierras in the freezing rain. This was our third attempt. Plan A got botched when I visited my grandma in LA. Plan B didn’t work out because I got COVID on our last day in Mexico. I guess the third time’s the charm? About 12 miles into the hike, fully drenched despite wearing rain jackets, we stopped momentarily and then both started shivering uncontrollably. We needed to get dry fast, and the only way was to pitch our tent right where we were standing. We changed into our only dry clothes and then fired up the Jetboil inside the tent to share an emergency hot chocolate.
Once the rain stopped around 5pm, I twisted the brown water out of my socks and put them back on. As the last sliver of light disappeared, we decided to descend a mountain of loose rock with no visible trail. Once we made it down, navigating around a large boulder field in the dark felt unwise, so we pitched our tent on the only small patch of dirt we could find, which wasn’t completely flat. At night, the wind shook our tent so violently that it felt like someone on the outside was shaking it. I had earplugs, so I quickly fell back asleep each time I was woken up, but Geo forgot to bring any. His watch said he got less than four hours of sleep that night.
I spent a week in NYC for work (a banking/fintech conference), but still made the most of my time there. I caught up with friends in Madison Square Park and hosted a Free Agents meetup at Bryant Park. I thought I’d want to prioritize eating at quintessential NYC restaurants, but I ended up gravitating more toward working out at Tonehouse, a fitness studio that trumps all other options. Mid-workout, it felt like descending into the next level of Dante’s Inferno, but post-workout, it felt like I had accomplished what I needed for the entire day and anything else would be gravy. Whether it was grabbing coffee, eating dinner, or working out, this trip reminded me of how much I enjoy quality time with friends. I flew back to the Bay with a dozen bagels.
While all these travels and weekend adventures were going on, I was also going through a job search. In contrast to last year, this time I had nearly the opposite problem. I was looking for my next role while still employed, and instead of struggling to get enough interviews, I had almost too many. Orchestrating the Tetris of interview scheduling alongside my job was stressful and required me to be always on. I was constantly taking calls and trying to move things along. I was herding sheep, trying to pace the various interviews in sync while still needing to do the actual prep. My strategy of leaving no stone unturned exhausted me, and it also worked. I’ll share more in a future post, but for now, I’m wrapping up my last week of work and taking some time off before starting my new role (it’s still a full-time tech job).
Life Intensification
A good way to distill the past few months is life intensification. Venkatesh Rao describes it as the “progressive fermentation and distillation of your life spirit,” the transition “from ethereal youth to fully alive adult maturity.” As I’ve gone from a single guy nomading in my mid-20s to rooted in one place with my partner, life has continued to feel denser and more concentrated, like muscle fibers adapting under load. There’s less mind chatter or hesitation about who I am and what I want in life. I resonate with Rao’s framing of becoming “a potently distilled version” of oneself.
Life intensification is adjacent to aliveness and ambition, but it’s not quite either. Aliveness often gets used in a spiritual, almost ethereal sense. Ambition is more future-facing: it’s about desire, trajectory, and what you want to make happen. When we speak of people with tremendous ambition, there’s a sense that they want to conquer the world and do everything. Intensification feels more grounded in the present moment and more intentional. As life gets denser, there’s a lot that gets deprioritized or let go of, but it also feels more distinctly mine. There’s greater care and seriousness, but also a stronger sense that the life I’m living is genuinely my own.
One way this intensification has shown up is in my relationship to ambition. When I left the tech industry over three years ago, it felt like walking away from a depleted tank. Those years spent exploring and trying different things helped me see how I could be ambitious about things beyond my job. Returning to tech last year was partly a means to an end, but it also helped me regain my ambition around work. I feel fortunate to know there are things that matter to me beyond work and money, while also caring again about progressing in my career, developing through my work, and making a solid living.
I had to accept who I was becoming. At first, returning to a full-time tech job felt like failing. I had already rejected one set of shoulds around climbing the corporate ladder, but without realizing it, I’d adopted another: escape the corporate world, be your own boss, build something of your own. Setting aside those preconceived notions of which pursuits were more noble required some humility. In turn, it made space for the unexpected to emerge.
The alternative to “growth” is not stasis or passivity, but a growing aliveness to the actual change that you’re undergoing in the process of generating responses to specific life challenges. If these challenges are real, then the way you change through responding to them is not entirely within your control.
For so long, we’ve been told that if we try hard enough, conjure enough willpower, and stay persistent long enough, good things will happen. I think this is true in certain contexts, like training for a race, but much less so in careers. A mere soldier ant understands its role in the colony, while we humans prefer to see ourselves as special snowflakes entitled to manifest the vision we set for ourselves. The harder realization was that the path in front of me was a decent full-time job in the industry I thought I’d never return to.
Escaping one set of shoulds doesn’t mean you’re free of them. It’s easy to reject the corporate ladder only to adopt a new script about entrepreneurship, freedom, or what a more enlightened life is supposed to look like. For me, paying closer attention to the actual rather than the should meant admitting that a job in tech makes a lot of sense right now.
In a crude sense, I was just going back to being a tech bro. I’m neither a Luddite nor an AI maximalist. One big motivation for working in tech is financial, but I’ve also been surprised by how curious I am about what’s happening in AI. So I’m leaning into that. Another surprise is that the stability of a full-time job has created room for new projects to sprout, like Free Agents and an outdoor food business I’ve been (literally) cooking up with a friend.
Paradoxically, the more seriously I take myself and my dreams, the more room there is for playfulness. I scrutinize how I spend my time and who I spend it with, but once I’m there, I’m there to have a good time. Whether whitewater rafting feels exhilarating or terrifying depends on your preparation, but also on your posture toward it. I’m learning that intensification isn’t about controlling the river. It’s about becoming more capable of meeting it.
Even though I feel like I’m living in a way that’s genuine and prioritizing what’s important to me, it can be confusing at times. I’m not my own boss, I set an alarm most nights, and I don’t have time to cook dinner every night. I’m rarely doing nothing, and during periods like a job search, a sense of restlessness follows me around. I’m more tired than I’d like to be or care to admit, but despite all that, there’s an underlying sense of peace and acceptance.
The overarching theme has been increasing my capacity for life. As I’ve gotten older, I’ve been able to take on more responsibility without tossing away the things I picked up along the way. I don’t write or coach nearly as much as I did when I wasn’t working full-time, but I still write and I still coach. These practices are no longer the main thing, but they’ve become part of the foundation. On top of them, I’ve added a demanding job, a loving relationship, new projects, deeper friendships, and other responsibilities.
It can’t just be a matter of adding new things, though. If intensification is a kind of distillation, it also requires subtraction. Compared to a few years ago, I travel a lot less and rarely go out at night. I read fewer Substacks and struggle to read consistently. I don’t watch much TV or sports, and I don’t play video games. Those movie theater subscriptions seem like such a good deal, but I don’t even think I’d hit the two movies a month needed to break even.
Life feels heavier and denser than it used to, but strangely, I don’t experience that weight as something I want to escape. I feel more connected to the people around me, more invested in what I’m doing, and more capable of carrying multiple parts of myself at once. There’s a feeling of fitting in with my environment and being prepared to adapt as I change and the world around me does too.
I imagine life will keep asking more of me and rearranging itself in ways I can’t anticipate. The goal has never been to figure it all out or arrive at a specific point. It’s to keep building the capacity to meet what comes without abandoning everything I’ve already learned to hold.
Other thoughts
I’m in my “post-quarterlife crisis, pre-kids” chapter of life. First came the tunnel-vision pursuit of a prestigious job, then the nearly three-year sabbatical saga, and now I’m in a new chapter. My hunch is that the next chapter will come after I have kids. From observing friends, getting married doesn’t seem to make a huge difference in the day-to-day, but having kids does. So what are my intentions for this chapter? I’d like the next couple of years to prioritize work. As someone who spent a while not working and advocating for others to give themselves a break (if that’s what they needed), that might sound odd. But for me, it’s about recognizing what feels right in this moment. Instead of viewing my work timeline as a linear progression toward escaping the systems we live in, I see it as cyclical, with the centrality of work ebbing and flowing. Right now, I’m appreciating the benefits of work and trusting that there will be time to prioritize other parts of life. When I have young children, I’d like to be in a position where I can choose to put family first, work second. I don’t think I’ll regret this chapter because I’ve already had a six-year period of free-spirited adventuring and wandering in my mid-20s. Who’s steering the ship, though? I recognize that it isn’t always me, my ego, or even my “higher self.” Sometimes it’s less about deciding and more about noticing where the current is flowing and not resisting it.
Instead of viewing a project or business mainly as a means to an end, I’ve been viewing it more as a vehicle to do more of what I want1. The question I pose to myself is, “If I keep building ___, what activities do I get to keep doing?” For Free Agents, that means spending more time with current members, having 1:1 chats with potential members, vibecoding products like our member directory, and facilitating the monthly calls. I like all of those things and want to keep doing them. Free Agents just happens to be the vessel that enables those activities. With the outdoor food business, I get to spend more time hanging with my friend Geo, hiking, cooking, and connecting with people who enjoy outdoor adventures.
The past few months reminded me of the importance of friendship. Not just having friends, but putting in consistent effort to keep those friendships alive and healthy. Work relationships are somewhat mandatory to maintain, and much has already been said about romantic relationships. Friendships are easier to let drift. As adults living in 2026, many of us don’t have school, church, the village square, or even the office if we work remotely. I wish I spent more time actually doing things with friends. I realized this not because friendship was missing, but because of the backpacking trips, dinners, board game nights, workouts, picnics, runs, and struggles at the golf range over the past few months.
If you made it this far, thanks for reading! I’m wrapping this up on my last day of work, and I’m flying out to Venice tonight with my mom. We’ll be hiking the Dolomites for ten days. Getting to travel with a parent feels increasingly rare these days, so I want to make the most of it while we still can.
Packy wrote about the same idea here, but I thought of what I wrote independently. I guess two people can come up with the same realization!
Loved this post and the growth in so many facets of your life. There are some banger moments of realization here that resonate a lot. Proud to call you my friend. Enjoy the Dolomites with your mom!
Hey Matt enjoyed this update and getting to know you a bit better. Hope the new job/chapter brings good things. Thanks for setting up and running Free Agents too!