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Strange, in a Good Way

From the Air Force Academy to Hong Kong, a van, and a house in Medellín: why seeing life slightly different than you grew up with makes it stick.

Ryan Cwynar5 min read

I'm on the boardwalk in Sheung Wan, Hong Kong, at sunset, jumping rope. My headphones are in, and Will Durant's The Story of Civilization is playing. The ocean is right there in front of me.

I remember that moment clearly because of what I was thinking. I was thinking about how strange my life had become. Not strange in a bad way. Strange in a way I was in love with.

Nothing special was happening. I was exercising and listening to a book. I could have done the same thing at home. But it wasn't home, and that was the whole point. Everything around me was slightly different from what I grew up with, and that small difference made the moment memorable. It made it beautiful.

I've been chasing that feeling for most of my life. This is the first thing I'm writing about it.

The urge

Since I was young I've had an urge for some kind of adventure. It's hard to explain where it came from. It just seems to have always been there. I wanted to see things that were different.

When it came time to choose a college, I chose a military one. I went to the United States Air Force Academy.

I don't think most people would put "military academy" and "adventure" in the same sentence. Looking back, though, it fits. It was a way to step out of the life I knew and into something with its own rules, its own language, and its own pace.

After the Academy I served. One of the moments I remember best from those years is a winter day on a military base in Boston, doing donuts in the snow in the parking lot outside the office. It wasn't exactly adventure, but it was the kind of small, slightly ridiculous moment that sticks with you.

When my service was over, I didn't go home and settle down. I went to Hong Kong.

Hong Kong

I was in Hong Kong in 2015, working for Asia Broadcast Satellite as a business development director.

That's the job description. What I actually remember is the boardwalk. The sunsets. The rope. Will Durant in my ears, narrating the history of civilization while I watched the sun go down over the water. The feeling that I had wandered into a version of my life I wouldn't have predicted.

This is the part I've been trying to put into words for years. It isn't that life abroad is better. It's that it's slightly different. The light hits the water differently. The streets sound different. The routines you've done a thousand times, like working out or walking to get food, suddenly have a frame around them.

When everything is a little unfamiliar, you pay attention. And when you pay attention, you remember. I think that's why so many of my clearest memories come from the places where I was a little out of place.

Waiting

Then I came back to the States for a few years.

I lived in a van. I learned how to code in coworking spaces. I did agency work and tried to make apps.

On paper that sounds like its own adventure, and in some ways it was. But the honest description of how it felt is this: I was waiting.

Waiting for what? I'm not sure I could have told you then. Maybe for the next thing to start. Maybe for a reason to leave again. I had seen what it felt like to live somewhere that made everything feel new, and coming back made the contrast hard to ignore.

I don't want to make those years sound worse than they were. Nobody needs to feel sorry for a guy with a van and a laptop. And I've started to wonder whether "waiting" was the right word at all.

Every coworking space where I sat and learned to code was building something. Every agency project and every app I tried to get off the ground taught me something I use now. Today I'm a software engineer. I'm a principal engineer, and I run my own small development business on the side. It's hard to imagine getting here without those years.

So were they a pause, or were they the setup? I go back and forth. Maybe it's both. Maybe sometimes waiting is just what building looks like from the inside.

Medellín

In 2021 I returned to the fray. I went to Medellín.

People talk about the weather here, and they're right to. The climate in Medellín is perfect. It's the kind of thing you stop noticing because it's always good.

You notice it when you leave. Every time I go back to the States, it feels like hitting an off switch on climate. One day the air is easy and you don't think about it. The next day you're thinking about it constantly. It's a small thing, but it's one of the clearest ways I can feel the difference between the life I grew up with and the one I chose.

Then there's the language.

After a couple of years, my command of the language got great. I know exactly when I noticed. It was the summer of 2023, about two years in. I got into an Uber at the airport for the ride into the city, and the conversation with the driver was easy. No rehearsing sentences in my head, no nodding along to things I didn't catch. Just talking.

Learning a language is the boardwalk feeling stretched over years. It takes ordinary things, like ordering food, talking to a neighbor, or reading a sign, and makes them slightly different. At first that difference is work. Then it becomes part of you. You start to live in two versions of the world at once, and both of them get richer.

And I bought a house here. It gets the basics right: high ceilings, a great view, and a lot of natural light.

A few years earlier I was living in a van and feeling like I was waiting. Now I own a house in Medellín, I speak the language, and I build software from here. When I put those two pictures side by side, it still feels a little strange. Strange in the good way.

What I've learned

If I had to pull one idea out of all of this, it's the one I had on that boardwalk in Hong Kong.

Seeing things slightly different from what you grew up with makes life more memorable and more beautiful.

It doesn't have to be dramatic. It doesn't have to be the other side of the world, although for me it has been. It's the small differences that do the work. A different ocean. A different language. A different climate that you only fully appreciate when it's switched off.

Those differences keep you paying attention. And I've found that the years where I paid the most attention are the years I remember best.

What's next

I've been in Medellín since 2021. Long enough to learn the language and buy a house.

And yet the urge hasn't gone anywhere. I might be at the start of the next chapter, one where I go even further. I'm not ready to say much about it yet.

But I recognize the feeling. It's the same one I had as a kid, and at the Academy, and on that boardwalk at sunset. The pull toward something slightly different.

I've learned to listen to it.

  • #life abroad
  • #medellin
  • #colombia
  • #hong kong
  • #learning spanish
  • #moving abroad
  • #software engineering
Ryan CwynarFull-stack developer and AI automation consultant, writing from Medellín. If this was useful, I also build this kind of thing for clients.Work with me →