There’s no shortage of stories about who you should be. Some are handed to you with love, others not so much. A few you carve for yourself, only to wonder later if they were ever really yours.
Over the past year—okay, four years—I’ve been sorting through those stories. I’ve outgrown some, avoided others, and buried one so deep that when it finally resurfaced, it both broke the masks I’d been wearing and made me feel whole in a way I didn’t know how to explain. Not to friends. Not even to myself.
This essay came from trying to do just that.
I.
Once a month, a group of guys in my neighborhood gets together for dinner and drinks. At the end of dinner, a new friend of mine, Matt, asked how my deep dive into education was going. He knew I’d been exploring the possibility of starting a school.
I laughed and hesitated. I’d recently picked up a thread I’d buried too many times, but I didn’t yet know how to put it into words. I told him I’d update him next time we had martinis.
Later that week, my wife and I had dinner with an old friend of mine. He asked the same question, wanting an update. As I began to explain myself, I felt a surprising deep sadness: I’d buried a part of myself so thoroughly, for so long, that even attempting to share it triggered a kind of antiviral response—from someone who I’d have said knew me well.
II.
For the last four years, I’ve been torn between two very different ways of being.
The first is the mode of the map: where a clear and communicable professional identity reigns supreme. The map is top-down, label-driven, legible. Our identity—our labels—give us a sense of direction. In map-mode, I am an executive coach to startup CEOs, an author, and a former founder. Or: I’m all that plus exploring the possibility of starting a private school. Got it.
The second is the mode of the territory: where there is no script—only a pull, a hunch, a whisper. The territory is bottom-up, label-last (if ever). You have to notice it. In the territory, I’ve realized I love coaching. But something’s missing. I think of my professional life as 100 points I can assign. Coaching claims a wholehearted 30. I don’t want to change that part. The remaining 70 stand in the corner, an elephant wearing a mechanic’s coveralls, complete with its embroidered name, wondering if I’ll ever put him to work.
I’ve tried on various things for the elephant, writing science fiction, exploring a master’s and PhD in clinical psychology, to name a few. But the more I’ve searched, the harder it’s been to explain what I’m doing to others.
The poet David Whyte wrote this:
“Ambition is desire frozen … The ease of having an ambition is that it can be explained to others; the very disease of ambition is that it can be so easily explained by others.” 1
When you look at a clock, you know it’s a clock. When you look at a person, how do you know if they’re a scientist, engineer, bartender, doctor, politician, welder, or painter? Well, they’ll tell you, right? But that very norm, that we can tell others who we are, creates pressure to declare it too soon. And that pressure is exactly what makes it harder to wander, listen, and keep exploring the territory until we hone in on what feels intuitively right.
III.
It’s October of 2024. My wife and I landed the plane on two momentous projects: getting married in June and moving across the country in August. My quest to fill the remaining 70, temporarily put on pause, could finally be picked back up. I walked downstairs to stare at our bookshelf. Something about Bertrand Russell’s History of Western Philosophy felt more “right” than anything else on the shelf. I’ve always wanted to explore philosophy, so I decided to trust that.
Sitting at the counter, I was struck by a theme in early Greek philosophers. They kept getting exiled. They’d then move to Italy and—naturally—started schools. A thought hits me, with even more “rightness” than the book on the shelf: maybe I should start a school.
Knowing how little I actually know about education, I decide to trust the instinct, but also shore up my ignorance. I throw myself into a six month journey, complete with ordering piles of books, reading some, pinballing between footnotes, academic papers, and articles. It all pairs nicely with the increasing usefulness of ChatGPT. For the first time in my life, I have something like a digital Aristotle to tutor me.
My sojourn through education brings me, fittingly, back to the Greeks. I encounter the source of the whole “first principles” idea I’d been attached to for years. Of course it’s Aristotle:
“To know a thing’s nature is to know its first causes and principles.” 2
I’d tried to read philosophy before, but I always abandoned it, finding it too dense, too opaque. I always felt like I was absorbing 20% of what I read. “Maybe it’s because I went to state school,” I’d think. But with Chat GPT, I decided to take a page from Feynman:
“I don’t know what’s the matter with people: they don’t learn by understanding, they learn by some other way—by rote or something. Their knowledge is so fragile!” 3
So I stopped myself from moving forward until I really understood what I was reading. I’d ask question after question until I felt that inner sense of clarity—of really getting it. And in one of the more meta moments of my learning, I discovered the Greeks had a word for that feeling: nous. Even better: I discovered it while learning about nous itself. I had nous about nous.
With nous as my new bar for understanding, and Chat as my Socratic guide, I found myself genuinely enjoying rediscovering Greek ideas. A number of them stood out, but one in particular stood out, and serves as a perfect segue to the next part of our story: mousikē.
The Greek’s idea of Mousikē is, yes, where we get our modern idea of music from. But what we understand as music is a shadow of what the Greeks meant. To them, mousikē wasn’t just rhythm, song, sound, or melody. It was the cultivation of taste, a critical part of a young philosopher-king’s education. It trained you to notice what you like, what you don’t like, what feels right, what pulls your attention.
And just like that, I had another word for what had been quietly guiding my search for the missing seventy.
IV.
When I was a kid, my Dad was generally a “we don’t hire contractors” kind of guy. So I ended up tiling floors, pouring concrete, planting trees, running electric, and even once electrocuting the poor guy (only mildly, thankfully). All these projects helped me begin to notice how some spaces just feel better than others.
A yard full of trees, flowers, and a fire pit felt richer than a minimalist lawn. A wood-paneled, warmly lit room laden with leather furniture did something to the soul that millennial gray linoleum and sheetrock never could. I didn’t realize it then, but I was developing a kind of mousikē, a cultivated taste, for physical space.
That love stuck around. In the ten years I lived in San Francisco building software companies, I found myself always noticing buildings, neighborhoods, and how thoughtful design could transform a place. I’d go on walks and lose my train of thought imagining how a street would look if only there were more brick, more trees, bustling ground-level shops, restaurants, and one of my favorite features: bioswales. Over and over again through the years, I’d arrive home from a walk a little let down, disappointed that these ideas lived only in my imagination.
Steven Spielberg said:
“The hardest thing to listen to, your instincts, your human personal intuition, always whispers. It never shouts.” 4
My intuition always called me to make things in the real world, but it whispered. I let myself get caught up in the shouts of the digital gold rush. I molded the part of me who liked to make things to fit the digital world, occasionally finding time to design this or that, even without any formal training, and often with dull-blade precision.
Looking back, a big part of me wishes I’d fed my inner designer more heartily while I was working on startups. I never became world-class, I never designed a production-ready product from start-to-finish, I didn’t ever invent anything. Instead, I learned to sell, hire, manage, fundraise, and write.
David Whyte, the same poet, also said:
“No matter the self-conceited importance of our labours we are all compost for worlds we cannot yet imagine.” 5
There’s a few ways to interpret that, but I think the idea that whatever we’re doing now is fertilizing soil for unimaginable new things to grow from is beautiful. My flirtation with the physical world continued, but my time in San Francisco was valuable. In many ways, it was an exercise in keeping doors open, collecting practical skills I could re-apply elsewhere down the road.
V.
In 2020 I left my role as CEO of Holloway. We’d hoped to build a product that enabled our users to ask books questions, opening up a new horizon of possibility for the curious. We didn’t deliver, but thankfully others did. One of my favorite writing tools now is to upload William Zinsser’s On Writing Well to Chat, give it my draft, and ask it what Zinsser would say about how to improve my writing. Failing to deliver on our ambitious goal, combined with a pandemic, left me feeling burnt out.
A close friend suggested I take a beat and try my hand at coaching other founders. Colleagues had always told me I was a great listener, something I’d never thought of as a technical skill like design is. As it turns out, listening is definitely a technical skill and a rare one at that.
On top of leveraging a strength, building a coaching business presented me with an opportunity to build a business all by myself. At a moment when I’d been rattled, I was left wondering if Holloway’s lack of success was me. I figured if I were entirely incompetent then I’d crash and burn. Instead, my coaching business thrived.
As I settled in to a strange new identity of advisor to startups instead of an operator, I set out to be the best I could. I identified a list of coaches people considered to be “the best,” met them or read everything they’d written, and while I didn’t always walk away unimpressed, I often did.
Somewhere along the way, I came across a wonderful book: Greatness by Dean Keith Simonton. As a coach to CEOs who wanted to be great, I figured it would be worth my time to learn what the research had to say on the subject, and Simonton’s 500 page review of the scientific literature did the trick. One line stood out to me in particular:
“…we might do better to say that all the motives that can stimulate the energies of the human being all converge on a single activity, a monomaniacal preoccupation.” 6
“What am I monomaniacally preoccupied with?” I thought.
My work with clients was, and continues to be, a mix of “outer work” (practical how-to advice: e.g., how to build a great hiring process, and so on) and “inner work” (emotional exploration: e.g, if you’re afraid of hiring people smarter than you, no hiring process will help). I began to notice which parts of my work stayed with me, which parts left me curious to learn more.
After a year or so coaching, I knew I had room to grow in the latter skill. Clients will often ask me, after a working together for a while, if we can spend a session talking about some difficulty with their spouse or significant other. I always emphasize that I’m not a therapist, but I’m happy to listen. This happened so often I decided to spend a year learning first about couples therapy and marriage counseling (it turns out a lot applies to executive teams and co-founders) and later psychodynamic psychotherapy. I seriously considered applying for a masters program with the goal of getting a PhD in psychology.
For a few years, I repeated a cycle from curiosity to study to application, and working with people began to feel like a real craft.
In June of ‘23, I came across this quote, by Richard Hamming:
“What are the important problems of your field? What important problems are you working on? If what you are doing is not important, and if you don’t think it’s going to lead to something important, why are you working on it?” 7
I love coaching founders not because I believe it’s one of the most important problems in the field of psychology, but because of each of my relationships with the individual founders feeds my soul. It’s the relationships, stupid. It’s helping people where I didn’t have help. It feels like healing to help people avoid some of the mistakes I made, to be there for them when I didn’t have someone. These founders are all so earnest, curious, motivated, creative, and want to do some good… maybe not all founders, but the ones I work with are. And helping these people get where they want to go feels great.
But the longer I coached, the more I realized it didn’t scratch every itch I had. I still wanted to build again.
VI.
In May of 2024, a CEO client asked me to facilitate their off-site. I figured I’d have some downtime to read, so I stared at my bookshelf (again) and waited for someone to raise their hand. Years earlier, my co-worker, Hope recommended I read A Timeless Way of Building by Christopher Alexander. I’d bought it, but I never opened it. For some reason this book stood out. I threw it in my bag.
The Urban Cowboy lodge in the Catskills is terrific.8 It sits on 200 acres of grassy hills and woods complete with fire pits, cabins, and a sauna all wrapped up in a mix of country and Brooklyn hipster. After wrapping up a day of facilitating, I headed to my room to sit in a luxe wooden soaking tup on my cabin’s patio, poured an old fashioned, and opened up A Timeless Way of Building.
At Holloway, our editor and now my dear friend Rachel Jepsen recommended I watch The History Boys, a comedy about a British headmaster’s attempts to turn eight rowdy students into university-ready gentlemen. In one scene, the headmaster, played by Richard Griffiths says to a student:
“The best moments in reading are when you come across something – a thought, a feeling, a way of looking at things – which you had thought special and particular to you. Now here it is, set down by someone else, a person you have never met, someone even who is long dead. And it is as if a hand has come out and taken yours.” 9
Reading A Timeless Way of Building was exactly like that for me. I texted my wife, “I think I want to build a neighborhood.” And it was only while writing this that I remembered I’d told her that once before, in 2021 while sitting at Flour + Water in San Francisco, eating their perfectly square layered lasagna. They took it off the menu soon after—one of the worst acts of value destruction I’ve ever witnessed in the restaurant business.
The quote that stood out to me most from Alexander was:
“The life of a house, or of a town, is not given to it, directly, by the shape of its buildings, or by the ornament and plan—it is given to them by the quality of the events and situations we encounter there.” 10
I flew home from New York knowing what I wanted to do. I couldn’t precisely articulate what it would look like, but I knew I wanted to play with physical space in a way that enabled the kinds of experiences that make people come alive.
And then life called. A few days later, Kate and I packed our bags for Europe for our wedding and honeymoon. The elephant would have to remain unemployed once again.
VII.
Kate and I are sitting in an Irish Pub in San Sebastián. The table is sticky, it’s raining outside, and I wanted a beer. We’ve been in Europe for nearly a month. We both know we want to start a family at the end of the year, and we know we don’t want to do it in San Francisco.
In part of my wedding speech welcoming our guests, I said:
Because, while a wedding is about two people, it’s about making sure we have enough people too. This wedding, this feast, this trip, all the hard work that has gone into this, is not just about Kate and I getting married, it’s our way of saying thank you for being there for us.
We knew we wanted to surround ourselves with great people wherever we went next. And for whatever reason, we had a group of friends in a hundred year-old village Christopher Alexander might admire. So that’s where we went.
Originally, we meant to buy a house, and I planned to use it as my laboratory to develop another type of knowledge the Greeks had a word for, technē. I’d renovate our house by hand, just as Dad and I had, and in doing so I’d be ready to do it for others. But we didn’t find anything we loved enough, so we decided to rent.
After we moved, decorated, and settled in, I sat down at my desk. I felt lost. And that’s when I went downstairs and picked up Bertrand Russell’s History of Western Philosophy.
One way of looking at my exploration of philosophy and education as a distraction. But more and more, I’m pretty sure it was just more compost.
VIII.
A few weeks ago, I walked on the brick sidewalks in my neighborhood appreciating that someone had the good sense to plant an abundance of lilac bushes. I walked by two houses I’ve walked by dozens of times, but something stood out I never noticed before.
At one point in time, these two houses were identical. Today, much less so. It reminded me of the cover of How Buildings Learn by Stewart Brand. One of the two has stood out to me repeatedly, tastefully renovated and added on to, and the owners have taken hobbit-level care of the lush landscaping. My kind of house. The house next door looks like it needs some love. I begin to wonder. Wouldn’t it be fun to work on the house next door or one like it?
At this point, I’ve told almost everyone close to me that I think I’m going to start a school. I have a website built for a podcast I’m going to start to learn more about education. I have a whole strategy. But I get home after walking by these houses, and “Are we going to do this or not, man?” The whisper asked.
A day or so later I’m walking by the same pair of houses with Kate. I point them out, tell her what I saw. She gets it immediately. I go home, I do some research. This is doable. I send photos of the houses to my friend in California who builds luxury homes (like, $20M homes luxury homes). He’s been to German Village. We talk for an hour. I’m fired up.
Instead of buying a house, living in it, and doing it all myself, I can leverage all the skills I learned in Silicon Valley: hiring, building a team, running the numbers, and even a mix of the taste—the mousikē—I’d cultivated for neighborhoods that feel alive. The idea of “flipping” a house as a passive investor makes me feel sick, but guiding a team, thinking of renovating a home as a “product” to craft feels closer to art and play.
Countless times have I had thoughts that I smothered and suppressed. Walking past the architecture building at Ohio State (it’s grotesque, by the way), “Maybe I’d like to be an architect.” Sitting on a Piazza in Italy or seeing the courtyards in Barcelona: “If we can bring European coffee to America, surely, we can bring this here, too?” And then I’d talk myself out of it.
But this time something different happened. I didn’t talk myself out of it. I leaned in. I tore up the map I’d been making for myself, embraced the territory. And what I found wasn’t surprising. To craft a heartfelt home is a small part of building a community that feels alive. I’m confident the act of building will lay more compost, from which maybe a neighborhood will grow, maybe more houses. Maybe something else, not buried like a secret, but like a seed.
IX.
Knowing yourself begins by listening to yourself. And after four and a half years sharpening my ability to listen to others, I suppose it’s no surprise that skill eventually turned inward toward whispers I’d spent years muting.
Finding professional nous—real clarity, to you—about what you want to contribute to the world is an act of exploration. And to explore is to get lost at sea and find your way back, often becoming more you along the way.11
But once you’ve found your way back, finally set on a course that feels right, there’s a special kind of sadness that comes from having buried a critical part of you so effectively that it comes as a surprise to even the closest of your friends. And just when you finally stop burying that part of yourself, your friends step in with the shovel.
David Whyte, again:
“The antidote to exhaustion is not necessarily rest… the antidote to exhaustion is wholeheartedness… You are so tired through and through because a good half of what you do here in this organization has nothing to do with your true powers… You are only half here, and half here will kill you after a while.” 12
It takes discipline to even aspire for wholeheartedness. It takes orders of magnitude more to find it and to commit to it.
I spent eight months exploring the idea of building a school. I had a strategy. I was ready to begin. And then, just as I reached the starting line, something more wholehearted interrupted.
The throughline wasn’t surprising. A school, a home, a neighborhood—they’re all just excuses to build community. The school: ambitious, exciting, needed, felt good. Building homes and one day neighborhoods: near-perfect occupational nous, impatient with waiting, ready for its moment.
X.
Ever since I can remember, I’ve loved RPG video games—story-driven adventures where your character grows through a mix of “main quests” that advance the plot and “side quests” that build your skills.
In those games, the difference is obvious. The quest log tells you what’s important. Real life isn’t so kind. There’s no blinking arrow above the next right thing. The paths forward exist only in your head, and their meaning lives in your heart.
The “side quest” into education led me to the Greeks: mousikē taught me to notice, technē to practice, nous to trust the feeling of rightness. It helped me recognize what I’d been silencing—and choose to embrace it.
If you learn to listen—to trust the whisper, to follow what pulls at you—you may not know if it’s a side quest or a main quest, but you can be sure it’s yours.
Footnotes