The One-Month Test

If you take one practical thing from this whole blog, let it be this post. Forget the big leap overseas for a second. The single best move we made — the one I’d recommend to anybody, no matter where you live or what your dream looks like — was renting somewhere for a month and pretending we lived there.

It doesn’t have to be another country. Start small. Start in the U.S. if you want.

Why a week is a trap

Here’s the problem with a normal vacation. You take your three or four days, and by day three it already feels like you’re heading home. The end is built into it from the start. You never actually arrive — you’re just visiting, and visiting tells you almost nothing about whether you could live somewhere.

A month is different. A month is long enough that you stop performing “vacation” and start doing life. You run errands. You find your coffee shop. You get bored, even — and that’s the point. You get to find out how a place feels on an ordinary Tuesday, not just on the highlight days.

And the math works better than people expect. Rent an Airbnb for a month almost anywhere and it’s comparable to — sometimes cheaper than — a week in Europe. As long as you can work remotely and don’t have to be in an office, what’s the actual difference? You’re just doing your same work from a better window.

So we went to Florida

Our first real test was a month in Florida — I think it was February, peak “get me out of this gray.” The goal was simple: do everything we’d normally do for the business, but from there, and act like we live there. Not a vacation. Go to the beach like locals, do the grocery run, find the routine.

We started in St. Petersburg for a month. Loved it. But — and this is the whole lesson — loved it still wasn’t the same as right.

We came home, the glow of the trip wore off over a couple of weeks, and I started doubting the whole thing. Looking back honestly, I realized I didn’t want to just trade one suburb for another suburb. The pool was great, the kids had more to do, walking distance to a park would’ve been amazing compared to where we live — where everything is “get in the car and go, and it has to be everybody’s consensus.” That walkability is a real benefit; I won’t pretend it isn’t. But a tenth of an acre in another subdivision wasn’t the answer either.

We tried another part of Florida for a couple of weeks. We looked at Fort Lauderdale — way too expensive for what we were trying to do. Everybody’s got their non-negotiables; we just hadn’t figured out what ours were yet.

What the test actually taught us

Here’s what a month gives you that a week never will. It surfaces your real questions:

• Do I actually like this climate, or do I just like escaping the bad one?
• Is 20 minutes from the beach too far? What about 10? What about on it?
• Do I want higher-density living — supermarkets on every corner, food delivered from six different places — or do I want rural and quiet?
• City or small town?

You can’t answer those from a brochure or a long weekend. You answer them by living it.

For us, the thing that finally killed Florida wasn’t the climate or the cost. It was school. We were looking for an alternative — not the public-school path, and the private options gave us sticker shock fast. We priced a really good Spanish-immersion school near us in Pennsylvania at $22–23k per kid, and with the extras it’s closer to $25–27k. (More on the school piece later — it ended up being the thing that cracked everything open.) Florida just didn’t have the alternative we didn’t yet know we were looking for.

Rent first. Always.

I know real estate — it’s been my world for a long time, and this is not a financial blog, so take it as opinion, not advice. But I’ll say it plainly: rent first. Everywhere. You don’t know what you don’t know about a place until you live there a little. We talked to an agent in Florida, started looking at houses, and quickly decided we’d rent no matter what.

Even in today’s economy, with where interest rates sit, renting can be a smarter use of your money than people want to admit — and it keeps you free. You don’t have to buy a house in Costa Rica or anywhere else. You don’t have to be tied to anything. A three-month rental, a one-month rental — that’s all it takes to explore, if you’ve got the ability to do it.

The point

Florida didn’t work out. But the one-month test absolutely did — because the goal of the test was never “find the place.” The goal was to find out whether this whole feeling we had was real, or just a fantasy that would evaporate the second things got inconvenient.

It was real. The boredom didn’t get cured by a month in St. Pete. If anything, it got louder. And that told us everything.

Next post: the thing a friend sent us that turned a vague feeling into an actual plane ticket. It’s called Boundless Life, and it changed the whole game.

— Brian