It’s been a fast month with dense memories.
I started off the month of May in Colorado. I realized I look for win-wins by allowing my work and personal life to blend and feed off each other. In this case, I volunteered to represent my startup at a conference. I knew it was in Colorado, and that’s where my friend Parker lives. At Denver’s Washington Park, we played volleyball surrounded by 50 other nets. On the first day of the farmers’ market, hundreds of vendors were selling cold brew lattes, breakfast sandwiches, and gourmet pop tarts. It was packed like a night market in Taipei.
As I walked slowly behind other people and angled my shoulders to avoid bumping into anyone, I felt the pulsating buzz of entrepreneurship. The farmers’ market (with few actual farmers), was full of courageous small business owners and met with equally eager customers. I thought to myself, “We need more of this.” People starting their own thing, pursuing their craft, and offering a great product to their local communities. Not just for food, but for everything.
I barely skied in March and had more or less given up on the season. But in May, I actually skied twice. Once in Colorado, then again in Tahoe.
Two days after I came home from Colorado and unpacked my suitcase, we drove up to Tahoe. Having a normal job again means returning to weekend warrior mode.
On Saturday, we played spikeball, kayaked, and hiked. After docking on the tiny shores by Bonsai Rock, Geo and I eventually worked up the courage (and stupidity) to swim out across our small rock to the cluster of big rocks. At the beach where we got our kayaks, they had warned us about cold water shock, implying that you should avoid the water entirely. But the water was turquoise and clear. Maybe there’s some primal urge in dudes to climb things. Without towels, we pretended to be lizards and dried off by sitting back on a small rock under the sun.
On Sunday, we skied. It was cold in the morning, but by the time we pulled up to the parking lot, we all needed to change into something lighter. I wore a t-shirt with my ski pants partially unzipped on the sides, exposing my bare thighs to the mountains. Instead of the ski goggles’ foam pressed up against my face, I opted for sunglasses and an extra-thick layer of sunscreen. Why is it that in February I was disappointed with the snow (or lack thereof) but in May I was just happy to be strapped to two planks of modern wood? Part of me is glad that I grew up on the east coast. I didn’t know any better when all I had was Whitetail ski resort on the border of Pennsylvania and Maryland. It was so fun skiing down that icy hill, oblivious to the bigger and better mountains out west.
The next week, I went to Chicago. First, I guest lectured at two classes at Northwestern’s Kellogg School of Management. Three months ago, I caught up with a former Uber colleague who’s now a professor there, and he invited me to speak. Leading up to the trip, I was stressed. I was spending the weekend in Tahoe having fun, which isn’t inherently a problem, except for the fact I had zero slides.
In the past, I was a skeptic of school and never considered pursuing an MBA myself. I resonate with Mark Twain’s idea of never letting my schooling interfere with my education. I’ve since loosened up. Macro-level chaos and disruption is catalyzing the transitions for many, both young and old. Universities, physical third-place institutions that have outlasted the ephemeral, provide the conditions for like-minded wanderers to collide like atoms in a lab experiment.
That was full on display when I met current MBA and other graduate students at Kellogg. Instead of spouting off cookie-cutter frameworks and executive leadership stories (I’ve never been an executive), I focused more on my boots-on-the-ground experience in my current role at a startup. My vantage point might lack a buzzy headline or a coherent narrative, but it does provide a peering into what it’s actually like to build a startup. Being in the messy middle, all I could share was our approach in business strategy and product development without the certainty of knowing if it’s going to work. We won’t know until we’ve tried and the dust has settled.
I ended up getting the slides ready a few days before my flight to O’Hare. I had prepared two different decks since I was speaking with two classes, but also because I would have 60 minutes with one and 90 minutes with the other. The night before the professor thought it’d be better if I just used the deck for the longer class for both. I went with the flow. I got to the Holiday Inn in Evanston at 11pm and was walking to campus the next morning.
Both classes went well. I never got through all my slides, but I didn’t need to. I tried my best to stay present and field questions from the students. Since I opted for tangible materials like product screenshots, real decisions, and active challenges we’re grappling with, students engaged with curiosity. A few walked up after class to ask follow-up questions and to keep in touch.
Recently, I’ve been revisiting some of my past ideas like “game of one” (my blog’s original name), “sustainable ambition”, “coherence”, “more human possible”. They’re all inspired by others or have been remixed from existing concepts, but regardless, they feel close to me. As I’ve changed, I’ve noticed that I relate to these ideas differently.
For example, take sustainable ambition. When I first wrote about it, I was pursuing coaching full-time, not making much money, and had far more free time. The “sustainable” elements were about patience, uncertainty, and orienting myself toward a long-term horizon. It was about trusting the process as someone in his first year of coaching.
Sustainable ambition means something different now. It’s about juggling the demands of a full-time startup job with other things like coaching, the Free Agents community, writing this blog, and more. I have other roles than worker or employee. Being a loyal friend and a loving boyfriend are just as important, if not more important than being a successful job-doer.
Sustainable ambition has expanded into more than just a way of approaching work. It’s for ambitious people who refuse to choose between earning well and living well. This is the crux, the false dichotomy, the challenge for so many people, including myself. Building a big life with meaningful work and healthy relationships is possible. It doesn’t require sacrificing your health, values, or weekends. It also doesn’t require completely rejecting corporate work and full-time jobs.
Just because it’s possible, doesn’t mean it’s easy. Hard work, like shoveling snow or mowing lawns as a kid, is necessary. It’s less about grinding until midnight everyday, and more about caring about what you do and how you do it. Elie Wiesel said, “The opposite of love isn’t hate, it’s indifference.” Indifference can manifest in different forms. It can be taking a fat paycheck to work on something you don’t believe in. Or by failing to embark on a quest of self-discovery and instead opting for herd-like behavior: buying stuff without intention, being jealous of your peers, and following celebrities.
Indifference is more subtle than rage or depression, and therefore more insidious. Like a leech. Indifference is what happens when I stop choosing and slip into defaults. When I let the algorithm, the status game, or the herd choose for me. When you’re indifferent, you don’t hate, but you also don’t love. It’d be like spending the rest of your life sitting on the couch eating mashed potatoes while watching Spongebob on repeat and not giving a damn.
Avoiding indifference is hard because we are inundated with tsunamis of information every day. To stay focused, I try to stay off social media, minimize phone time, exercise daily, eat nourishing foods, and read books instead of tweets. I’m not always dialed in. This month, YouTube and Instagram got the best of me. I stayed up too late and paid for it in the morning. I’m not a protocol maximalist but I do remind myself that everything compounds over time, good or bad. Next month, I’ll try to be better.
What’s indifference got to do with sustainable ambition? Everything. It’s impossible to do great work while living well without focusing only on things you care about. There isn’t enough time plus I don’t have the energy for my job, loved ones, projects, working out, books, and falling for cute but AI-generated pet videos on TikTok.
Sustainable ambition, for me right now, is not about doing everything. It’s about clearing out what leads to indifference, so that I can care deeply and work hard.
Random Stuff
It’s felt like summer for the past couple weeks. We went fruit picking in Brentwood. First, we picked mulberries (a sweeter, longer blackberry) that isn’t sold in grocery stores because they perish so quickly. They were plentiful and given the $8 entrance fee, I ate over 100. Cherries were next. At first, I thought the only trees with any fruit left were the ones that required climbing, so I climbed them. That was fun. But then we kept walking and found trees dotted with red all over. By the time we got to the third farm for the peaches and nectarines, I had eaten so much fruit I couldn’t sample any more.
I haven’t prioritized things like meditation, therapy, or retreats so far this year. I guess I just had to be patient. I’ll go on a solo retreat in August and then a big community gathering later in September. It’s hard to make space for both turbo startup life and zen monk vibes. But at least I’m trying.
Splendor is our new favorite board game. It’s simple: you collect different colored things to buy things so you can buy bigger things. Last night, after we grilled outside while watching the Spurs when game 7, we had four teams of two crouched over our coffee table competing and talking shit. Big fun.
I’ve gotten back into reading this year. This month, I read The Lost Symbol, Breakneck, and Runnin’ Down A Dream. My favorite part of Breakneck was at the end, when the author Dan Wang reflects on what kind of life he wants for his parents. Of all places, he highlights Sunset Park, Brooklyn as the epitome for Chinese folks living in the US. I couldn’t agree more. I lived in Sunset Park for six months during my recent years as a jobless wanderer and I’ll always reminisce my daily morning walk to Sunset Park. I’d get a sweeping view of Manhattan and be greeted with the lively sights, sounds, and smells of a community at play.
I updated my website with a photography section, refreshed Now page, and a new orientation for my coaching practice. Let me know what you think!
breakneck is an incredible book