From Businessman to ‘Existential Explorer’ – An attempt to explain what I’m doing

2 years out of work, 1 year of writing, and a new lens on living [Existential Explorer: Intro]

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The Way of Work explores stories of where we fit in the world of work. This is an introduction to my 5th series, Existential Explorer - Ideas at the Edge of the Map, exploring the uncharted edges of who we become when we try to matter.

Check out my last series, Not Obvious (why work advice fails us), The Other Side of Enough (what’s life is like when you have enough).

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Nearly two years ago, I left the traditional working world at the age of 38. I found myself with time, freedom, and a gnawing sense that there was something more important to figure out than how to make more money.

The world was wide open, but I struggled to find my footing, having exited a system that once gave me structure, identity, and external metrics of success.

I thought that in the space away from work, I’d find clarity. Instead, I found more questions. Not just the “what do I do next?” variety, but also the “who am I?” ones, even some unexpected ones, like “why do I need to do anything at all?” There’s nothing quite like spending decades building a fortress of identity, only to have it crumble once you finally settle in.

Two weeks into my newfound freedom, I broke down crying to my wife. I felt alone. No one seemed to understand what I was going through. And there was guilt for questioning a life that had turned out so well. Is there anything less sympathy-inducing than the privileged guy in the midst of a midlife crisis?

One year later (a year ago), I decided to turn away from my old career to start writing. My wife will attest the day that I “went public” with this news was surprisingly emotional. Not just because I sent my first essay to a whopping 127 people (btw, thanks for everyone who has shown up since). But because it marked the beginning of an identity shift, stepping away from a place where I knew I could excel, into the unknown.

From early startup to $2B public company, what 12 years at Privia Health taught me

I’ve found that many people, when faced with similar questions of existential weight, go back to what they know. They handicap their own transformation by not sitting with the unsettledness, and working through it. Instead, they go back to the world they’re comfortable with. Or they swap one game for another, off the treadmill but back on a new one. They want to get themselves back on the map.

And honestly, I almost did the same, originally intending to become an Even-More-Important-Person with the next logical thing that one does in my situation. Some of you think that, armed with freedom, you’d do this or that. But just you wait… the scaffolding holding up your identity largely goes unnoticed, and when it vanishes underneath you, you’re left grasping for almost anything that can put you back on solid footing.

Meanwhile, the price of not going back induces a special kind of nausea. I had close to a million reasons to stay. Instead, I chose to start over in a new endeavor, with no promise of success. I chose to fumble around when others ask me “what do you do?” I chose to put my earned reputation in risk of ruin. No big deal!

But I chose not to go back, despite the unease. Or at least I was willing to wait out the tension a little while longer. I sensed that there was something for me, out across the open horizon, even if I couldn’t see anything there. And if I kept going, I thought I’d discover it, whatever it was.

Turns out, I did.

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“Why am I here?”

At first, I thought writing was just a side project. Something to do in-between other things, while I reconciled the old me and figured out a new one. A way to keep myself occupied, rather than sliding into irrelevant oblivion.

Now, I realize that writing was the point. Or more specifically the exploration behind the writing.

One of the first lines I ever wrote still sticks with me today. It’s “the why” behind The Way of Work:

“help us find our place in the world of work.”

Whatever chaos is happening out there, we ultimately must find our place within it. While the macro changes shape the world, the micro questions carry existential weight. And the wrong lens can be the difference between a life that feels like a calling or a curse.

I know my writing is hard to label – I jump around – at least within the conventional, boring category of work or career advice. I find most of the space suffocating, ranging from feel-good (but useless) platitudes, flat either/or thinking, or “things worked out for me so they will work out for you too” blowhards.

We have deep questions about work, but the answers out there are shallow. We get productivity hacks, motivational fluff, and the same-old recycled career advice. I’m just not interested in that stuff anymore.

What I am interested in is questions of meaning and identity, with “work” as the vehicle to explore them. Because how we think about work, including its familiar themes of success, ambition, and freedom, reflects who we believe we are. Scratch the surface, and you’ll find the real stuff underneath: love, legacy, morality and mortality.

For example:

I’m less interested in what jobs AI will take,
and more interested in how we find meaning in a world without work.

I’m less interested in how to “succeed at work,”
and more interested in why success matters in the first place.

I’ve tried to write not as an expert, but as someone thinking out loud while walking the edge of the map. I have no desire to be the go-to-guy in any specialized domain. I’m too imprecise and clumsy in my approach. My skill is more in poking and provoking than in providing polished answers.

That’s why my tone changes. My format shifts. Each series is a way to test myself and the boundaries of my identity. Each essay is a way of making sense of my past, my own evolutions, and where I’m going next. These are methods of exploration, breadcrumbs left behind for anyone interested in following the spectacle.

The Way of Work: Series Index

It hasn’t always been smooth. I’ve gotten in my own way – overthinking, trying to outsmart the instincts that brought me here. I’ve chased originality, dodged cliché, and occasionally disappeared into the fog of my own expectations. I reject formulas, but secretly wonder if I should invent my own. External validation is a shallow game, but I still track my metrics religiously. It’s hard to take the businessman out of me.

I asked AI to roast my writing,¹ and it came back with some uncomfortably accurate stuff:

“You’re the kind of guy who escapes the rat race… and then builds a new maze in your mind.”

Yup, sounds about right. Also:

“You loathe gurus, yet flirt with becoming one.”

C’mon, AI! Why you gotta play me like that?!?

The truth is I get stuck in my head, over-intellectualizing everything (this essay may provide some evidence). Sometimes I wonder if I’m on the verge of a breakthrough or a breakdown.

But I’ve found the payoff is so much greater when I lean into the unknown. Sure, exploring the frontiers of oneself requires risk, but the reward is discovery. Especially, when I embrace what I think I’m really doing: being an Existential Explorer.

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A New Lens on Living: An ‘Existential Explorer’

I want to introduce a new concept that I’ve never heard used before: Existential Explorer. It’s a bit abstract (on purpose). And yes, it sounds a little pretentious (also on purpose 😉).

“No one knows what it means, but it’s provocative!” - Will Ferrell

However, I think it captures what I’ve been circling this whole time. It combines two ideas:

Existentialism - explores meaning and identity, especially through the lens of the individual experience

Explorer - someone willing to head into uncharted territory, without needing to land anywhere too long

Put them together, and you get a certain type of person.

An Existential Explorer wants to understand how people make sense of their lives and their place within it. They study not just what people do, but why they do it.

They look at how we can construct a life outside of predefined structures (teaser for my next essay). They don’t just pick a popular purpose off the shelf. They check the ingredients. Try different brands. And sometimes leave the store to forage for something wilder.

An Existential Explorer starts with not trying to answer the questions, but trying to question the answers. The seeker in them is less concerned with finding “The Unifying Theory of Everything,” and more so wants to explore, and ideally live, what it is to have a good life.

They reject the illusion of rigid frameworks in favor of movement, curiosity, and contradiction. Instead of chasing certainty, they embrace ambiguity. They see the paradox in people without needing to flatten them out.

It’s a place where freedom is real, but so is uncertainty. They must contend with what it’s like to navigate without a map. The endeavor requires plenty of tangents and side quests. Some lead to strange and beautiful places. Some lead nowhere.

Identity gets slippery here too. Even following a big discovery, they are content to sail off again, never landing too long. Value is in the exploration, not the destination.

Failure is getting stuck when it’s time to move on. Or worse, wandering off into the infinite horizon, lost in perpetual confusion.

And most inconveniently, there's no money in it! Lest you believe I'm pitching some great new career opportunity… I’m not! There are many great reasons to write and explore, but don’t fool yourself that money is one of them. Yet.

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I think this moment in time is ripe for existential exploration. Most of us have let our big questions get sidelined as we slog through our days. But the systems we lean on are cracking and the narratives we inherited don’t hold. A bit more poking around would probably be good for us.

Meaning is up for grabs. Institutions won’t save us. And AI will make us question our place at the top of the food chain. Living inside a world in flux, our place in it can feel so small and fragile. Some hunker down. Some numb themselves with distraction. Others try to punch a dent into the world.

Or, like me, you can move to the edges of the map. At the very least, you can watch me send myself into the void. I, for one, would rather be lost at the edge than asleep at the center.

What will be discovered out here (if anything)? We’ll see. I’ll do my best to let you know as I go.

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⍰ Question: What do you think of the term ‘Existential Explorer?’ What resonates or not with you? Comment below.
🙏 My Ask: the only way writing gets discovered by new readers, is when it’s shared. Please ❤️ or 🔄 or send it to a friend.
👀 Next up: I cover The Open Frontier of Meaning (maybe my most ambitious essay yet).

The Open Frontier of Meaning

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1. Credit to

Khe Hy

for the inspiration. You should check out his new newsletter, Future-Proof Your Career With AI, which has a very practical approach to playing with AI.