In my early fifties, I set out to become a full-time investor. That was the plan for my second career — clean, familiar, and built on twenty-plus years of stock market experience.

That’s not where I ended up.

Today, I’m building stock analysis tools in code, turning them into a web app, and constructing a media platform across two WordPress sites — one in Korean, one in English. A few weeks ago, I filed for a business license. The solo startup is now official.

This newsletter is where I document all of it: how I got here, what I learned, and where I stumbled along the way. If you’re in your forties or fifties and the question of “what’s next” keeps surfacing — I hope this is worth your time.

Why Ten Years?

I don’t call this retirement planning. That framing never quite fit. What I’m doing is preparing for a second career — and the distinction matters.

When I started thinking about it that way, a simple question followed: how long did it take to build my first career? There was school, credentials, years of trial and error, slow accumulation. It didn’t happen quickly, and it wasn’t supposed to.

Why would the second one be any different?

The world is also changing in ways that make this less of an edge case. Staying in one career for an entire working life is getting harder. Two or three careers across a lifetime is becoming the norm rather than the exception. If that’s true, then a second career deserves the same seriousness — and the same runway — as the first.

I Started With What I Wanted

This time, I reversed the usual order. Instead of asking what I could do, I asked what I actually wanted.

The answer had been sitting there for years: I wanted to spend a month at a time in places I’d never lived — moving slowly, with family, without a fixed address pulling us back. Not tourism. Something closer to actually inhabiting different parts of the world.

That wish had one practical requirement: location independence. Whatever I did for income, it couldn’t be tied to a desk in a specific city.

When I held that condition up against my experience, one answer surfaced immediately. Twenty years of investing. If I could do that full-time, at the level I’d need to, I’d have everything: flexibility, familiar territory, and work I already understood.

That’s where this story begins.

Then Things Went Sideways — In the Best Way

I started as an investor trying to get better. I ended up somewhere I never expected.

To improve my analysis, I started digging into data. To manage the data, I started writing code. As the code grew, I wondered if other investors might find it useful — so I began building a web app. To share what I was learning, I started writing. And once the writing had somewhere to live, the idea of a proper media platform took shape: WordPress, bilingual, built to last.

Somewhere in the middle of all that, I filed for a business license.

I started out wanting to be a better investor. I’m now, apparently, a founder.

How that happened — the decisions, the detours, the things I got wrong — is what this newsletter is for. I’ll share it here, one piece at a time.