Millionaire Librarian

I’ve been thinking lately about which choices actually got me here — not the spreadsheet-optimized version of my financial life, but the real one, messy timeline and all. Some decisions I got right for the right reasons. Some I got right for reasons I’m not proud of. And at least one thing I got wrong, and I’m still not totally sure I’ve learned the lesson.

The Corolla, Not the Tacoma

My first car was an almost-new Toyota Tacoma. Solid truck. It lasted a decade before it was totaled. When it was time to replace it, the obvious move — the move my younger self clearly wanted to make — was another Tacoma. $34,000 and years of payments.

I bought a used Corolla instead. Thirteen grand. A small Japanese econo shitbox, if I’m honest about how it felt at the time.

There was no dopamine hit in that decision. Nobody’s impressed by a Corolla. But the $21,000 gap between those two options, left alone in an index fund, is worth more today than either truck ever was. This is the least emotionally satisfying and most financially important car decision most people will ever make, and most people make it wrong.

The Years I Was Broke on Purpose (Sort Of)

There was a year I lived in real poverty, working part-time at Best Buy. My wife has a theory about that year: I didn’t actually want a full-time job, I wanted to keep living like I was still in college. She’s probably right, or at least half-right. It doesn’t fit neatly into my “good decision” pile, and I’m not going to force it to.

What I’ll say is this: the instinct that kept me living small during that year didn’t go away once I started making real money. When I finally had extra income, I didn’t inflate my lifestyle to match it — I kept living the same simple way and put the extra into a Roth IRA. Whatever the origin story of that instinct, delayed gratification, low materialism, whatever you want to call it, it’s the actual engine under almost every good financial decision I’ve made. The Best Buy year might have been avoidance. The investing years after were the same trait doing something useful.

The House I Sold When I Should Have Rented It

I bought cheap and small instead of trying to match the house my parents had. That part I got right. Where I got it wrong: I sold that house later instead of keeping it as a rental. Low mortgage rate, appreciating asset, built-in tenant demand — it looks like free money from where I’m standing now.

I try not to be too hard on myself about this one. Hindsight is 20/20, and low rates always look obvious in the rearview mirror. In real time, a rental property is tenant calls and maintenance emergencies and vacancy risk, and I was not in a financial position back then to absorb a bad year of that. It’s fine to let this one go as a reasonable call given what I knew, rather than a mistake I should still be kicking myself over.

Marrying Well

I married someone who genuinely enjoys a simpler life. This is not something I engineered — it’s closer to the biggest single input into everything else on this list. Expensive tastes, or a divorce, would have been financially catastrophic and emotionally worse. I don’t take full credit for this one. I got lucky, and I recognized the luck, which is maybe the only skill involved.

Debt-Free by Luck and a Little Planning

I worked at a university that paid for my master’s degree. Mostly luck. Some planning. But graduating debt-free gave me flexibility that compounded for years afterward — flexibility to move for jobs, flexibility to take career risks, flexibility to eventually walk away entirely. Debt doesn’t just cost you interest. It costs you options.

Money as a Mental Health Tool

Part of what good financial decisions bought me was the ability to make good decisions for my mental health. I moved across the country for a job once, and that move cost real money — thousands of dollars most people in a similar spot simply don’t have sitting around. Financial slack isn’t just about retirement projections. It’s the ability to leave a bad situation, or move toward a better one, without the decision being made for you by your bank account.

The One I’m Still Not Sure About

Here’s the one that actually nags at me. I had a great position. Genuinely good. I left it anyway, chasing more money and a better place to live, moving one state over. The new job turned out to be a mess, and that mess is a big part of why I ended up retiring early.

I love how it turned out. I want to be clear about that — I’m not writing this as regret. But I can hold two things at once: I love the outcome, and I’m not convinced I needed to blow up a good situation to get there. If I’d had the wisdom to just be happy where I was, a few more years at that other job would have been perfectly fine too.

I think the actual lesson isn’t “always take the leap” or “always stay put.” It’s narrower and harder than that: have the wisdom to recognize a really good thing while you’re still standing in it. That’s a skill I’m not sure I have yet. It might be the kind of thing you only learn by blowing up a good situation a couple of times first.

What This Adds Up To

None of these decisions look impressive individually. A cheap car. A small house. A boring index fund. Staying married to someone low-maintenance. None of it is a hot tip. But laid end to end, it’s the entire mechanism — every dollar not spent on a bigger truck or a bigger house became a dollar that could buy freedom later. The math is simple. The hard part was never the math. The hard part was wanting the freedom more than I wanted the Tacoma.