Freedom Without Constraints Is a Trap

A few weeks ago, I came across a post by a fellow Substacker. Cory Gerlach, who writes Radical Paths, published a piece called Why Your Freedom Isn’t Working.

It stuck with me. Not because it was a new idea, but because it named something I’d been feeling for a while without being able to articulate it.

So I sat down and tried to dig into it. What follows is what came out.

📸 Escaping regular life in Japan

Settled, Comfortable… and Half as Productive

Since settling in Bangkok, I’ve been less productive than at any point in the past five years. By roughly half, if I’m being honest.

That’s a strange thing to admit when life looks great on paper. We have a beautiful apartment - a real one, with a standing desk, a big monitor, two couches, a swimming pool outside. After years of Airbnbs and hotel rooms, it feels luxurious. We have friends here, a social life, a city with something always going on.

And yet. I’m getting less done than I was when I was living out of a backpack.

For a while, I couldn’t understand why. Now I think I do.

The Constraints I Never Chose

When Rosie and I were traveling full-time, our days were essentially binary: work, or explore. That was it.

No couch to collapse on. No TV to flip on. No pool to drift into “just for 20 minutes.” We’d be in a simple studio or a basic Airbnb room - functional, but not comfortable in the way that pulls you away from things.

There was also real financial pressure. Work wasn’t optional. It funded the next leg. If the month went badly, it showed up quickly and concretely.

And there was something else - a kind of built-in intentionality that came from always being somewhere temporary. You’re in a city you might never return to. You don’t want to waste it. So you either work - seriously, productively - or you make the most of where you are. There’s no default third option of just... drifting.

We had what felt like total freedom. And in a real sense we did - no office, no fixed address, no boss, no routine we didn’t choose.

But looking back, we also had constraints we never consciously designed. They were just part of the structure of that life. And those constraints made us focused, efficient, intentional.

What Bangkok Removed

The apartment changed things in ways I didn’t anticipate.

The physical comfort is the obvious part. There are now much better things to do than work. The couch is genuinely comfortable. The TV is big. The pool is right outside. Bangkok itself offers an endless feed of restaurants, friends, events, things to explore. At any given moment, there are a dozen more attractive options than opening my laptop.

But there’s also a subtler thing that happened. I set up a proper office - standing desk, big screen, dedicated space. Which is great. Except that now, in my head, “work” happens in the office. If I’m not in the office, I’m not working. And in the evenings, I want to be on the couch with Rosie, not alone at a desk.

So the thing I built to protect my work time ended up rigidifying it in a way that worked against me. There’s an irony there.

The financial pressure also changed. Earlier this year, I took on a part-time freelancing gig - 20 hours a week, afternoons only. It covers all our expenses, plus a bit more. Which is a genuine relief. But it also removed the urgency I used to feel to grow my own business. When you’re not under pressure to perform, you... don’t perform as urgently. I know this is short-term thinking. The gig will end eventually, and I’ll have to hustle again. But right now, the pressure isn’t there - and I can feel its absence.

It’s also interesting that this is coming at a moment where - once again - I find myself questioning my path. I wrote about a similar feeling last year, though the circumstances were different. That liminal space feeling is back, quieter this time, but familiar.

The point is: two forms of comfort arrived at the same time - physical and financial - and the combination hit harder than either would have alone.

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The Invisible Architecture

I’ve spent most of my adult life chasing freedom. Freedom from a 9-to-5. Freedom from a fixed location. Freedom to decide how I spend my days.

And I got it. I genuinely have it.

What I didn’t realize until now is that during our nomad years, we had freedom AND structure - we just didn’t design the structure intentionally. It came built-in to the lifestyle. The bare rooms. The financial precarity. The temporariness of every place.

Remove the lifestyle, and the structure disappears too.

What I’m left with is freedom without constraints. And it turns out that combination is a recipe for drifting.

I work well under pressure, when my back is against the wall. Right now, there’s no wall. So I float.

Where I’m At

I don’t have a clean resolution for this. I haven’t figured out exactly which constraints to reintroduce, or how.

But I’ve at least named the problem - which is more than I could do a few months ago. I knew something felt off. I knew I was moving slower than I wanted to. I knew the comfort was connected to it somehow. I just couldn’t articulate the mechanism.

Now I can: I removed the invisible architecture that was holding me up, and I haven’t replaced it with anything.

Nature has seasons. Some people will say a slower period is fine - even healthy, like hibernation. Maybe. But it doesn’t feel like a choice I made. It feels like something that happened to me while I was comfortable.

And the difference between choosing rest and sliding into stagnation is significant.

I’m not someone who wants to grind 60-hour weeks anymore. That drive is gone, and honestly, I’m okay with it. Quality of life matters to me. Bangkok gives me that.

But I do want to be moving. I crave growth and forward motion - it’s just part of how I’m wired.

So the work ahead is figuring out which constraints to put back in place. Not to punish myself. Not to recreate the pressure of precarity. But to rebuild the structure that lets me move.

I’ll let you know how it goes.

J