It’s Not a Crisis. I Checked. Twice.

Why the hardest part of making a transition isn’t the move, it’s the conversation

I traded the goal of accruing more wealth for the goal of collecting experiences.

Working abroad looks different when your commute involves a stop at the leather shop

Before I moved to Vietnam, I told a few people it was time to shake things up.

“I’m not virtue signaling,” I said. “I’m just redefining my own ambition…but don’t ask me what I mean by that just yet.”

Most [not all] smiled and said almost all the right things. And it wasn’t lost on me how much that meant, coming from people who are as intelligent, driven, and exacting as they come.

The kind who don’t hand out unearned encouragement. For that, I’m grateful. But even with their support, I could see the questions flickering behind their eyes:

“Is he giving up?”

“Is this a phase?”

“Is this a crisis?”

“Do we need to hide the sharp objects?”

I can’t blame them. They’d known me for years. I’m not the barefoot-in-the-grass kind of free spirit people picture when they hear that phrase.

I’m more intense. Fiercely independent, always on my own path, but with enough polish to make it seem like I’ve got a master plan in my back pocket.

Maybe it’s because I’ve never really felt like I belonged anywhere, so I made damn sure I’d be someone worth emulating. I’m not exactly thrilled to admit that. No adult is.

We love to declare that we’re too old to care what others think, but most of us still do; hence, a billion-dollar industry aimed at emotionally immature adults.

And that’s exactly why this move felt so out of character to people who knew me. They didn’t entirely get it, but they got that it was purely for me, not for likes. And that in itself is a giant leap for adult children everywhere.

It's not a crisis. I checked. Twice(though, let’s be honest, if it had been, it would’ve been a very organized crisis).

Redefining Ambition Without Burning It All Down

It’s easy to think I ditched ambition. But I still feel ambitious. I’ve got a lot in the hopper and I’m grinding it out.

But the target is different now, and I’m much clearer today about what I meant when I first said I was redefining ambition: I traded the goal of accruing more wealth for the goal of collecting experiences.

This was no small shift for someone wired like me. And unless you grew up on a deserted island, most of us don’t choose our ambitions. They’re planted. By parents. By culture. By the threat of foreclosures.

Maybe even by that one family member’s offhand comment in high school you’ve been unconsciously proving wrong ever since.

And the thing about inherited ambition is… it often works. At least at first. You get to tick the boxes, say the lines, and feel like you’re on the right track. More importantly, you get to keep a roof over your head.

Until one day you’re not feeling on track anymore and you can’t quite explain why your to-do list feels so hollow. And then it hits you: You’ve been living out a story someone else wrote.

Not the wrong story per se; just someone else’s story.

From Founder to “Perma-Vacationer”

All this came into sharper focus during some… let’s call them illuminating conversations during our last trip to the States. Somewhere along the way, in the popular imagination, I’d been promoted to “perma-vacationer.”

It’s not malicious. Just the shorthand people reach for when your life takes a hard turn and rather than looking distraught, you have the nerve to look content.

Especially when the rest of the world feels like it’s on fire and your crow’s feet have mysteriously vanished.

I mean, how can I expect anyone to picture me working when my “commute” is dodging coconuts on a motorbike and stopping for a second iced coffee I definitely don’t need?

It’s particularly tricky for people early in their climb into adulthood. They can grasp it in theory, but not yet in their bones the idea that work, struggle, and success wear a thousand different faces.

For now, it’s still just a concept, not a truth they’ve lived.

When you’re young, you mostly believe what’s right in front of you. And what’s in front of them is someone living abroad, posting photos of beaches and markets, and not clocking in anywhere.

Honestly? I would’ve thought the same thing in my 20s. And in my 30s. Hell, even in my early 40s. Most of us would. Most of us still do.

Why I Keep a Rehearsed Answer Ready

There’s a thing about perception worth noting here. It has momentum. Once people think they’ve got your life figured out, every detail becomes part of that story in their heads.

If you’re not careful, the conversation stops being about who you are and starts being about who they think you are.

I don’t have a silver bullet here. No foolproof wisdom. But I have learned this: Winging it is overrated.

You can be as “authentic” as you want, but when your choices are unconventional, unplanned authenticity often just leaves you saying too much. And as my mom used to say:

“When you say too much, Stephen, I know you’re unsure about what you’re saying.”

So now I keep a short, honest-but-rehearsed talk track. Something I can put on repeat so I’m not caught off guard or explaining my life like it’s a courtroom defense. Mine goes like this:

“It’s not about checking the next career milestone anymore. It’s about finding myself in moments I couldn’t have planned, much less scheduled. I swapped the currency, from dollars to days I actually want to remember.”

Does that land every time? Not really. Sometimes it still makes people tilt their heads like they’re waiting for the punchline. Which is fine.

And when I don’t have the stomach for anything more, there’s always: “I just want a life I love.” It’s fuzzier, sure… but sometimes vague is better. It leaves space for people to imagine a life they’d love too.

And maybe that’s the only part worth explaining anyway.

Because I’m still working on it.