We just spent a month living in Japan with three kids, all five and under. I ran my businesses the whole time.
This year my wife and I sold the first business we started nine years ago. We still run a few other things, and the reason we could leave at all is that we spent a long time building them to work without us standing in the middle of everything.
The month looked like this: Tokyo on the front end, then Matsumoto and Nagano, then three weeks based 30 minutes south of Toyama out in the rice fields. Weekends in Kanazawa, Katsuyama, and Himi. Kyoto for two days at the end. Most of it was in the Japanese Alps, which we'd never spent real time in before.
For three of those weeks our kids went to a local Japanese preschool through a program called Japan Preschool Exchange (preschool-exchange.com). They handle the housing, the kids are in school 9 to 4, and you just live there.
Three things I'd tell anyone thinking about it.
1. You miss less than you think. I built a month away up in my head as this huge disruptive thing. Then we got home, started catching up with people, and it had been life as normal for them too. Nothing was on fire. That one realization is what makes the next trip feel possible.
2. It is not a vacation. I worked. You build a rhythm to the days the same way you would at home. The hardest part was the fourteen hour time difference, which put our day squarely in their night and made staying in sync genuinely hard. Europe would be easier just from the overlap. What saved it is that our team is remote-first and spread across time zones already, so somebody was always awake. That's not luck. It's how we built it, and it's the same thing we do for other companies through RemoTeams, which is my company.
3. You can't plan around everything. Our daughter got sick the last four days and missed school. Stuff like that is going to happen.
We're homeschooling this fall so we can commit to this properly. I think trips run somewhere between three weeks and three months. We're still figuring out what works.
We do still have businesses that need us. We're opening Domo, a mindful cafe in Houston, and a new cafe is not a leave-it-alone situation. But I feel good about the systems and the people we've put in place.
I'll be writing about how we're actually doing it as we go.
A month abroad with three young kids while running businesses sounds impossible until you do it. You miss less than you expect. You still work. And things will go wrong no matter how much you plan.
The key is building systems and teams that don't require you to be in the middle of everything. That takes years, but it's what makes extended travel possible.
If you're thinking about doing something like this, start building toward it now.
