Cold Feet, Costa Rica, and How We Actually Choose Where to Live

Uruguay gave us confidence. Costa Rica tested it.

After our 90 days in Uruguay with Boundless Life, we came home for a month — and almost talked ourselves out of the next one entirely. This post is about that, and about the actual system Katie and I now use to decide where in the world we point the family. I get asked about the how more than anything, so here it is, honestly.

The month of doubt

We’d lined up Costa Rica next — this time going direct to a school ourselves, not through a program. And during that month back home, everything got shaky.

Our son got sick. I questioned all of it. Are we really doing this? Should we be doing this? We had the tickets. We had everything booked. And we still changed those tickets twice in the final week and ate hundreds of dollars in fees doing it. It was one of the hardest decisions we’d made — we didn’t fully commit until the last possible moment.

I tell you that part on purpose. The Instagram version of this life skips the night you’re sitting there with a sick kid and a non-refundable fee wondering if you’ve lost your mind. We didn’t skip it. We lived it, we got our clarity, and then we went — I left first with the kids, and Katie joined us shortly after.

We made it out the other side. And on the other side was Costa Rica, which earned its way high onto our list and confirmed something Uruguay had started: we love the beach, we love the Spanish-speaking culture, the food, the people, the sports (I’ve gotten hooked on paddle). We’ll dive deeper into Costa Rica in its own posts.

The framework: how we actually decide

Early on we made these decisions on pure feeling. Now we use a framework — and yes, we lean on AI to help us think it through. Not to make the choice for us, but to organize our own heads, because when you’re emotionally in the mud it’s hard to see clearly.

We borrowed the idea of starting from a vision: not “where’s a nice place,” but what do we actually envision our lives to be, and what matters most? Then we broke that vision into categories and let a place earn points against them. Roughly, in our priority order:

1. School (first, always). We’re building this entire life around the kids. The right alternative school isn’t a tiebreaker for us — it’s the foundation. Everything else comes after.
2. Safety.
3. Beach. A close second after school. After La Barra and Costa Rica, we know for sure this one’s near the top for us.
4. Time zone. This is a big one people miss. We run a business. Working opposite hours from home wasn’t conducive to what we actually wanted — which is to be with the kids as much as possible outside of school. If we’re working all evening while they’re asleep, what was the point? The time zone has to be compatible with the business.
5. Infrastructure. Can we actually live and work here without fighting the place every day?
6. Spanish-speaking. We find the culture genuinely interesting — the people, the food, even the sports. We started building our life around that rather than stumbling into it.

The order shifts a little depending on the place, but school sits at the top of every list. That’s the anchor.

Use AI as a thinking partner, not an oracle

Here’s how we actually use it, in case it helps you. We don’t say “AI, where should we live.” We feed it our vision and our categories — sometimes prompting it through the lens of a framework or a book we like — and we treat the output as a first draft of our own thinking, not the answer.

We do the human part first: talk it out, sit with the feeling, get our gut read. Then we bring in the AI to pressure-test it and fill in the gaps, because sometimes you can’t see what you can’t see when you’ve never lived a thing. Gut first, then the tool, then back to us. That loop has gotten us unstuck more times than I can count — and we feel stuck all the time, so don’t think the people doing this have it figured out. We don’t.

You don’t have to blow up your life

I want to be careful here, because there’s no right way or wrong way to any of this and I can’t say that enough. This might not be for you, and that’s completely fine.

But if it is — know that the barrier is lower than it looks. You don’t have to buy a house in another country. You don’t have to be tied to anything. You can find a three-month rental, a one-month rental. You can change jobs, find a remote one, build flexibility into your life. If you put the goal out there, plan for it, and talk to people who’ve done it for motivation, it can absolutely be something you actually do. And get your spouse genuinely on board — make sure it’s something they want too, not something they’re being dragged into. That part matters more than any country on the list.

It’s never “done”

Here’s the honest ending: we haven’t arrived. We still don’t fully know what we want. We’re on our third rendition of this life now, and each place narrows it down a little more — what we like, what we don’t, which spots give us happiness, or solitude, or that feeling of getting to write our own rules and not live to anyone else’s standard.

I’ll leave you with the same thing I think about driving through suburban Pennsylvania on a Friday afternoon — every door closed, and I genuinely can’t tell you where any of the kids are. Mine are outside in the grass as much as I can get them there. If sitting in a driveway is the whole adventure, that’s just not enough for me. And there’s so much more out there — and it doesn’t have to be another country. It could be anywhere in the States.

So: live outside the box if you want to, or live in the box if you want to. Just know the box can be broken at any moment, and you can go anywhere. If you’re not happy where you are, or you’re just a little bored — go look for something else.

Thanks for joining us on the journey. More to come — including the trip we haven’t even told you about yet.

— Brian