The Text Message That Changed Everything

We’d done the Florida experiment. We’d proven to ourselves the itch was real. But we were stuck — we had the feeling and no vehicle for it. We knew we wanted something different, we just couldn’t see the path from a month in St. Pete to actually raising our kids somewhere else in the world.

Then one of my best friends — Mark — sent us a link to a school called Boundless Life.

”You have to see this”

I watched the first video and called Katie down from upstairs. The kids were at her parents’ house that morning, so we had a couple of rare quiet hours to ourselves. We sat there and watched it together, and I’m not exaggerating — within the first 20 minutes we both knew. This was the solution to the problem we couldn’t figure out how to solve.

We booked an intro call that same morning. It was a Saturday, so we couldn’t actually talk to them until Monday or Tuesday — but we were that sure that fast.

If you’ve never heard of it: Boundless Life is a program that came out of the COVID era. As I’m writing this they’ve got around nine school locations across the world. You join a cohort — primarily a three-month stay (they’ve started doing a one-year option too) in one of the countries where they’ve established a school system. They set you up with housing, a rental car, bags, insurance — it’s close to a “done for you” experience.

It’s not cheap, and it’s not for everybody. You pay a premium for the plug-and-play. But for us, where we were, it was a blessing — because what it really bought us wasn’t logistics. It was people.

The part I didn’t expect: the other families

Here’s what blew our minds. We walked into a community of families who had all felt the exact same pull we had — and we’d had zero access to people like that before.

These were parents with kids the same age as ours. None of them had it all figured out either. But they all had the same quiet calling: we want to do something that isn’t like everyone else, and we don’t care what people back home think. Our parents can come visit us, or we’ll go visit them — but this is our life, and we’re going to live it the way we want.

The amount of information we picked up from those families — practical, real, “here’s what actually works” information — was staggering. It gave us a confidence we didn’t have on our own. It’s the difference between reading about a thing on Instagram and sitting across a table from someone who’s living it.

Uruguay: our first solo family trip abroad

In September 2025 we did it — our first 90-day living experience in another country, in Uruguay, with Boundless Life.

I won’t pretend the start was magic. Two flights, about twelve hours total, arriving in the middle of the night. I got a ticket on the drive in. Our son cried on the last leg. You’re sitting there at 2 a.m. questioning every decision: what am I doing dragging my kids through this? Nothing about travel ever goes perfectly, and that first stretch will test you.

And then you get a few hours of sleep, and the next morning you walk down to the first open café, and you order lemonades for the kids and coffee for the adults — and right there, that first morning, it’s already worth it.

It took us a little while to fall in love with La Barra. There were things we just weren’t used to; it was our first big trip, and every place has its pros and cons. But over time it became this beautiful little world:

• The teachers and school director were outstanding — genuinely blew us away. So warm, so good at what they do.
• They set us up with a working cohort, so Katie and I could actually get our business hours in during the day.
• Our daughter took surfing lessons. Both kids did art class and a couple of after-school activities — which also gave us a bit of time to ourselves.
• And the kids started learning Spanish. They’d never been introduced to another language in their lives. How do you explain to a three- and five-year-old that there’s a whole other language out there? You don’t — you just put them in it, and they pick it up shockingly fast. They started listening to people talk and understanding. That there are other cultures out there, that the world is bigger than your street — I don’t think that can be taught. You have to be there.

What Uruguay really gave us

I don’t want to glaze over the experience itself — we’ll come back to Uruguay in its own post, because it deserves more than a few paragraphs. But from the journey standpoint, here’s what mattered:

Boundless Life and those three months were the eye-opening experience that handed us our confidence. For two entrepreneurs who’d never been out of the country longer than ten or twelve days at a stretch, doing three months was something we’d never come close to before. It was, in the truest sense, a starting point. It taught us what we actually wanted — a Spanish-speaking culture, the school-first mindset, the kind of community we wanted our kids around.

It laid the groundwork for everything that came next.

And what came next was Costa Rica — which is also where this got hard. That’s the next post: the cold feet, the tickets we changed twice, and the framework Katie and I now use to decide where in the world we go.

— Brian