To win, position well. To position well, realize it’s a choice. 

“Why do people live here?”

It’s a common refrain when I travel. And I travel a lot.

Between 2018 and 2025, I lived in a van, driving around the U.S. and Canada. For 4 months in 2022, I lived in Australia, New Zealand, Japan, Indonesia, and South Korea. And most places make absolutely no sense to me.

New Orleans, New York, San Francisco: I get. Austin, Seoul, Paris, Tokyo: totally. But Chicago? Kansas City? Cleveland? Dallas and Houston? Those tiny towns in Nevada and Colorado and Oregon with more elevation than people?

I’m in Chicago for a friend’s wedding. A surprise thunderstorm shook our windows. Two years ago when I visited, I heard a siren. I asked my friend: “What’s that siren for?” He said it’s a weather warning: we were about to be cold enough to be deadly.

The trains run above ground (terribly noisy), and most don’t even run all night. The weather is always either too hot or too cold. The theater and art are good, but not as good as New York or L.A. The food is tasty, but overwhelmingly unhealthy. Maybe it’s the sports?

I don’t buy that most people intentionally choose where to live based on their values and preferences.

Where & why? 

Ask people why they live where they live (I do, constantly) and most people give one of 4 answers:

1. They were born there. (This is Partner’s most frequent response when I pose the question.)
2. Work or school took them there.
3. A lover took them there.
4. It’s the nearest city to where they were born. (Partner grew up in the “big city” for her area, because it had a Walmart. This “big city”: 16,000 people.)

Who’s the actor here? 

Every answer describes something that happened to the person. Born there: the game placed you. Work took you: the company (or admissions committee) chose. A lover took you: the lover chose (or their company did). Nearest city: the game placed you, plus a radius.

Where you live is one of the biggest decisions in your life. It decides your environment, your friends, your culture, your wages, your rent, and your weekends. And it’s a rare big game where most players never even realize they’re playing. The board hands them an opening setup, and they just accept it.

I can count on one hand the friends who chose their place to live by auditioning and deciding.

Reality & possibility

How many people decide where to go? Between 18 and 30, do you explore while you can (no mortgage, no kids, career still portable)? After your kids leave home, do you think about moving?

Money, visas, family gravity: there are good reasons to stay where you live. But a lot of it strikes me as activation energy. You’re a distinct person with individual tastes. And you just happen to have been born in exactly the right place? 

I’ll take the other side of that bet.