Who's Choosing
TL;DR: I caught myself chasing an impressive-sounding idea I didn’t actually want, and realized I’ve always been driven by who I become rather than the problem itself — which makes the problem dangerously interchangeable. So I’ve stopped asking what’s most impressive and started asking what’s real, what I’d help people get unstuck on, and whose world I can’t stop thinking about.
I talked myself into an idea I didn’t actually want
Two months ago, I finally overcame my own fears and decided to take a bet on myself by starting my founder journey. Fast forward to today, I caught myself chasing an idea I wasn’t truly excited about.
It was in investment banking — the world I came from before my stint at Artie, where I figured I had the strongest founder-market fit. The logic was clean. I knew the users, I could resonate with their pain, and I could get the meetings with the right decision-makers. It felt like the responsible bet, and I thought running with an idea is better than sitting around searching for ideas — at least I’d learn a thing or two in the process instead of getting caught in my own thoughts. Truth is, I had already spent about 2 weeks trying to come up with ideas that I considered to be worth working on and I quickly felt anxious about the time elapsed. So once the story lined up and made sense to a handful of those around me, I decided to run with it.
It took me longer than I’d like to admit to see what I was doing. I wasn’t choosing a problem. I was choosing the most defensible-sounding vehicle and reverse-engineering a reason to want it. And once I noticed that move, I started seeing it everywhere in my past — because it turns out I’ve been doing it my whole life.
I’ve always survived hard things by calling them rungs toward becoming a CEO
I didn’t grow up wanting to be a founder. I wanted to be a CEO. The people I looked up to — Jobs, Gates — happened to be founders, so founding became the path, but the destination was always the chair at the head of the table of a company that mattered.
That goal explains some otherwise strange decisions. I went into investment banking, but not for the reason most people do. I wasn’t there for the prestige, the money, or the optionality. I went because I wanted to see, up close, what companies look like when they’ve actually scaled — what good management looks like, how the sausage gets made. Banking was hard, but I made peace with it the same way I made peace with everything hard: I told myself it was an investment, it would end, and it was buying me something I needed. I’d used the same trick in school (study hard, become a top student) and in the military (two years out of society, framed as an option I was buying for my future). Every difficult season was bearable because it was temporary and instrumental — a rung on a ladder toward the person I was trying to become.
Then I joined Artie as the first business hire, and I’d be lying if I said it was purely strategic. The honest version is that I was afraid to start my own thing. I couldn’t think of an idea, and I’d quietly glorified founders into people who had it all figured out. Working next to them cured me of that fast — founders don’t know most of it either; they’re just willing to act anyway. I stayed for about two years and got exactly what I came for: a front-row seat to how an early company actually gets built. But every quarter I’d have the same uncomfortable conversation with myself. Why am I still here? What am I still afraid of? I kept punting, partly because the work was genuinely all-consuming, and partly because punting was easier than admitting I was using a great job as a place to hide. Eventually it became obvious that staying was the thing standing between me and the thing I said I wanted. So I left to make room.
If I’m chasing who I become, any problem will do — and that’s the danger
Here’s what all of that adds up to, and it’s not entirely flattering.
I’m not, at my core, a missionary — someone who falls in love with a cause and would chase it whether or not it ever pays off. And I’m not a mercenary either; I’m not in this for a number. I’m a third thing. I’m driven by who I become through the work. The company is, on some level, a vehicle for becoming the leader I’ve always pictured myself being.
I consider it to be a powerful engine — it doesn’t run out the way money does, because I’m essentially never finished becoming. But it has a dangerous flaw when it comes to choosing what to build: if the point is me, then the problem is interchangeable. I could drift, very logically, toward whatever makes the most impressive CEO-story rather than whatever is most real. That’s exactly what those first two months were. The status-seeking part of me — and yes, I care about status, and about money, enough to want to provide for my family and to be taken seriously when I try to help someone — dresses itself up as strategy and points me at whatever sounds good at dinner.
I don’t think the answer is to pretend I’m someone purer than I am. The answer is to point the engine at something that keeps it honest.
Helping people get unstuck is the one thing I’ve never had to force
Underneath all the ambition, there’s something simpler that I trust more.
The thing that has always lit me up — long before any of this — is being the person someone leans on when things are hard. Korean students finding their footing abroad, players struggling to fit in with the rest of the rugby team, friends working out how to break into banking, or make the jump into startups, or navigate something with their family. It’s never really been about the topic. It’s the act of helping someone get through their most pressing hardship and watching them get unstuck. I’ll give hours to that without thinking about what it returns to me, which is more than I can say for most things I do.
And it reframes the status thing in a way I can live with. The version of impressive I actually want isn’t glamour. It’s being proven right about something critical that everyone else underrated — taking a problem people dismiss as boring or small and showing that it mattered all along. Turning the unsexy into the undeniable. That’s the kind of win that feels like mine.
Now I ask whether a problem is real, not whether it’s impressive
I’ve stopped asking “what’s the most impressive thing I could build?” and started asking better questions.
Is the pain real and acute — the kind where even a rough first version is necessary, not just nicer or cheaper? Will someone pay for it quickly, because willingness to pay is the most honest signal that I’ve made something people actually value? And — the one I think matters most — is this a customer whose world genuinely fascinates me? Because I know myself well enough now to admit that left to my own defaults, I’d rather talk to my team than to customers, and I’d treat customer conversations as a duty rather than a pure delight. The only fix for that is to choose a world I can’t stop thinking about, so that obsession becomes fuel instead of obligation.
I don’t have the idea yet, but I finally know who’s choosing it
There’s a question I still can’t fully answer, and I’d rather be honest about it than fake a tidy ending: what gets me out of bed in year three, when the novelty is gone and there’s no outside milestone left to chase? My whole life, the thing that carried me through hard seasons was knowing they were temporary and that they were building toward a next rung. A company isn’t temporary, and “become a founder” is a goal I complete on day one. So I’m going to need a different kind of fuel than the one that’s always worked for me. My best guess is that it has to come from the problem itself and the people I’m solving it for — that the ambition has to be anchored to something real, or it floats off into prestige and leaves me stranded.
I’m writing this down partly so my cofounder knows exactly who he’s building with — the drive and the blind spots both — and partly because I think the only way to choose well is in the open. I don’t have the idea yet. But for the first time I think I’m understanding the shape of the person who’s choosing, and what would make me proud to have spent a decade of my life on it.