It Never Started With a Single Day

Let me get one thing out of the way first, because people always want the clean version of the story: there wasn’t a single day. There was no moment where Katie and I looked at each other across the kitchen island and said, “That’s it — we’re taking the kids and raising them overseas.”

It didn’t happen like that. It crept in.

It came from a hundred little pieces — Instagram reels at midnight, a comment from my brother, a friend texting me a link, the same gray Pennsylvania sky four winters in a row. By the time we actually got on a plane, the decision had already been quietly making itself for years. I just hadn’t noticed.

So if you’re sitting where we were sitting — a nice house, good kids, a business that works, and a low hum of “is this really it?” underneath all of it — this first post is for you. This is where it actually began.

The part nobody tells you about “the dream”

Before kids, Katie and I traveled. Egypt, Dubai, most of Western Europe, Iceland, Hawaii. We loved it. We knew kids weren’t on the radar yet, so we went and we soaked it up.

Then our daughter came — right in the middle of COVID, 2020. No travel. You’re in the baby phase, you don’t know what you don’t know, and honestly we weren’t comfortable going anywhere even if we could have. Fifteen months later our son arrived, so we locked back down, raised both kids at home, and built a business.

And the whole time, that wanting-to-travel feeling never went away. It just got buried under the traditional life. We’d built our house in 2016 — this was supposed to be the forever home. Ten years later we’re in it a few months a year and trying to figure out whether to sell it, rent it, or what. We’re not fully divested from it yet. I’ll be honest about that as we go.

My honest problem: I get bored

I’m going to say something that not everyone will relate to, but it’s the truth: I get bored fast. The redundancy, the day-in-day-out monotony — it’s always gotten to me. When we first moved into the house, no kids, freedom to travel, I didn’t feel it as much. Once the kids came and the routine set in, it came roaring back.

I’d play the tape forward in my head: the kids get older, we pick them up off the bus, ride bikes in the yard, maybe hit the local trail. A couple of vacations a year like every family — maybe a few extra because we work for ourselves. And that’s the whole movie. That’s the rest of it.

For some people that’s a beautiful life, and I mean that. For me, something about it felt like settling for the highlight reel instead of the actual thing.

COVID, strangely, was the catalyst

Here’s the part I didn’t understand until I started talking it through out loud.

My brother once asked me how I felt about not having to go to all the social stuff during COVID — the birthday parties, the baby showers, the weddings. I hadn’t even thought about it, because we’d quietly built our own routine. Every moment of every day was on our schedule. Nobody could disrupt it, because nobody could see us.

And I think that was the seed. We got a taste of writing our own rules, and we never wanted to give it back. You get a version of that same feeling traveling abroad — you’re removed from the default, removed from the social machine, and you finally get to ask: what do WE actually want our days to look like?

The Pennsylvania winter math

If you want the most concrete reason, here it is. Pennsylvania gives you about five months where there’s no real snow on the ground — just overcast skies, wet brown everything, and sunsets at 4:45 in the afternoon. You get the kids off the bus at 3:30, maybe they’ve got a sporting thing after school, and by the time that’s done it’s dark and you’re all inside.

You do that for multiple months a year, every year, and at some point you ask a simple question: why?

That question is where Four Passports starts.

The thing we keep coming back to

We work hard for the flexibility we have — and I don’t take it for granted. When you own your own company you’re “on” seven days a week to some degree. It’s the fun and the burden of being self-employed; you’re not completely free, you’re just free-er. But that freedom is the whole reason this is possible, and we earned it.

There’s no right way or wrong way to do any of this. This might not be for you, and that’s fine. But for us, living in the same place our entire life — and choosing to go on vacation instead of living somewhere we’d want to vacation — stopped making sense.

As our logo says: 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. If you’re a little bored, a little un-satisfied even though you love your friends and family — that’s not a flaw. That might just be the first piece.

In the next post, I’ll tell you the cheapest, lowest-risk thing we did to test all of this before we ever left the country. We call it the one-month test.

— Brian