A Personal Story
Around the World, Just Us
When people find out I took my kids around the world, the first question is usually some version of "how." How do you afford it, how do you school them, how do you keep working. The honest answer is that the how came second. First we decided that the life we wanted had the world in it, and then we built everything else around that decision. This is the part of my story I usually keep off the rest of the site, because the site is for the work. This one is for the why.
A few years ago I sold my law firm and moved my family to the west coast of Puerto Rico. I had spent two decades architecting other people's businesses while quietly neglecting the architecture of my own life. The move was the first repair. The travel was the second.
Europe, by the window
We started by crossing Europe by train. There is a particular kind of education in watching one country turn into the next through a window, no airport in between, the language on the signs changing while you are still mid-sentence. The kids learned to read a departures board before they could drive. They learned that being lost is usually temporary and almost always interesting.
Africa, sitting very still
We went on safari in Africa, which humbles a person in a way no classroom can. You spend your whole life as the thing at the top of the food chain, and then you sit very still in an open vehicle while something much larger than you decides whether you are worth its attention. The kids did not need that lesson explained. They felt it.
The road, and a bear
We drove Route 66 from one end to the other, no schedule and no hurry, the way it is meant to be done. We kept our distance from a bear in Alaska, which has become the story the kids tell first, every single time, with increasingly generous details about how close it actually came. We set foot on every Hawaiian island, one at a time, until the map had none left to give us.
Twenty-seven countries, just us
Twenty-seven countries, stamped alongside my children, just us. We worldschooled the whole way, half because we believe seeing the world is part of an education, and the other half because I wanted them to grow up understanding that work is supposed to serve the life, not the other way around. That belief is easy to say at a conference. It is harder to live. The travel was me deciding to live it.
What it proved about the work
Here is the part that surprised even me. The businesses kept running. For months at a time we were on the road, and the companies I had built did not need me standing in the building to function. That is not luck, and it is not a brag. It is the same thing I now design for other founders: a business that runs on systems and trusted people instead of on the owner's physical presence. The trip was the proof. If the architecture holds while you are watching elephants on another continent, it holds.
I do not believe you have to leave to learn this. The lesson was never really about airports. It was about deciding, on purpose, what a life is for, and then refusing to let the work quietly take the parts that matter most. We designed it on purpose. Everything I build now, for myself and for the people I work with, starts from the same instinct.