I was living cheap in Chiang Mai. Then I moved to Singapore and everything changed. (2025)

When I close my eyes and picture Chiang Mai, I still feel it in my body. The soft morning haze, the weightless freedom of a day unstructured, the aroma of black coffee from a roadside cart, the calm that seems to drip from the trees. It was all so effortless, so beautifully slow. For a long time, I thought that was the point.

I had found a life that didn’t cost much and gave me space to breathe. I could work from anywhere, eat well for a few dollars, live in a modern apartment for less than a fraction of what it would cost in Sydney or Singapore. And best of all, no one around me was rushing. There was a strange solidarity in the slowdown. It felt like I had opted out of the madness and chosen something wiser.

I wasn’t alone in that feeling. Chiang Mai became a digital nomad magnet for a reason—cheap, comfortable, and just chaotic enough to feel like you were living an adventure, while still being cushioned by Western conveniences. You don’t have to explain yourself to anyone there. You just sort of arrive and dissolve into it.

But over time, something started shifting in me. And at first, I didn’t know how to name it. It wasn’t boredom. It wasn’t loneliness exactly. It was more like a dull hum of dissonance. Like I had slowed down too much and couldn’t find the gear to shift back up.

In the early days, I romanticized my life there. I saw myself as intentional, conscious, deliberate. But what I’ve come to understand, years later, is that I was actually hiding behind the ease. And that hiding was shaping everything—my business, my identity, even how I engaged with the culture around me.

I’ve written before about why so many digital nomads are leaving Chiang Mai, and the strange spiritual paralysis that can emerge from a life that costs so little. But what I didn’t fully unpack then – what I want to share now – is how my own evolution was catalyzed by leaving. Not because I was fed up with Chiang Mai. But because I was ready to stop coasting.

When I moved to Singapore, it wasn’t for the lifestyle. No one moves here for the lifestyle, at least not in the same way. It’s not cheap. It’s not easy. And no one’s giving you a spiritual gold star just for showing up. It’s a place that demands structure, precision, and an unapologetic commitment to doing the work.

But strangely, that’s exactly what gave me peace.

You see, in Chiang Mai I had freedom. But it was external freedom – low cost, low stakes, few obligations. What I didn’t realize was that I was paying for that freedom with my potential. Because when life doesn’t demand much from you, you stop demanding much from yourself.

That became painfully obvious to me in how I was building Brown Brothers Media. I had ideas. I had reach. I had traction. But my systems were sloppy. My focus was scattered. I’d work in sprints, then disappear into slow-living fantasies, telling myself I was “recharging” when really, I was avoiding friction. Singapore gave me the friction I needed.

This city has an intelligence to it that you can feel. Things work. People move with purpose. The bar is high – not just financially, but mentally, emotionally. You can’t float here. You have to choose your direction and then commit. And that commitment brings something I didn’t expect: spaciousness. Not in the cheap-rent-and-yoga sense. In the I-know-what-I’m-doing-and-I’m-doing-it-well sense. The kind that settles your nervous system.

The paradox is that I found true stillness in a place of constant motion. Because here, my inner world had to become structured. I built systems not to escape from, but to live inside. My business grew. My clarity sharpened. My ambition stopped feeling like something I was secretly ashamed of, and started becoming an expression of my values.

But there’s another layer I need to address – one that’s more uncomfortable, but essential to name. And that’s the subtle disconnection many of us, myself included, live with in places like Chiang Mai.

I’ve touched on this before, but the more time passes, the more I see it clearly. We often convince ourselves that we’re integrating into local culture just because we eat street food or know a few polite phrases. But the truth is, many Westerners live in parallel societies in Southeast Asia. We occupy physical space, but not emotional or social space. And as Lachlan argued in his piece, this separation breeds resentment. Even if it’s unspoken.

And it breeds something in us too: a low-level spiritual malnutrition. Because humans are wired for belonging. And you can’t belong to a place you don’t fully engage with. You can admire it. You can consume it. But you can’t be of it.

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In Singapore, integration is different. It’s not warm or fuzzy. It’s not performative. It’s systemic. You contribute, or you don’t exist. You find your place not by claiming space, but by adding value. You don’t blend in by dressing down – you blend in by showing up. And that does something to you. It humbles you. It makes you sharper. It teaches you to listen.

When I lived in Thailand, I would sometimes catch myself looking at locals and feeling like an observer. There was a glass wall I couldn’t name. Now I realize it was self-imposed. A product of a lifestyle that allowed me to live adjacent to the culture, not inside it.

And here’s the truth: that lifestyle has a role to play. For many, it’s a lifeline. A reset button. A space to start over without the suffocating weight of Western expectations. I get that. I needed that too. There’s no shame in choosing cheapness and ease when what you need most is healing. But if we stay too long in that space, it can calcify into avoidance. And the longer we avoid friction, the more it costs us – creatively, relationally, spiritually.

What I learned is that sometimes the most spiritual thing you can do isn’t to slow down. It’s to build something. To get rigorous. To get uncomfortable. To move toward complexity, not away from it. Because inside that complexity is where your next evolution lives.

In Chiang Mai, I spent a lot of time in cafes with people who felt exactly like me. Same values. Same aesthetic. Same complaints. We were seekers, but also skeptics. We wanted meaning, but we didn’t want the systems that meaning sometimes requires. We opted out before we fully opted in.

And then I moved here, to a city where no one is particularly impressed by your story. Where no one congratulates you for “living life on your terms.” Where the currency is not identity, but execution. And it was the best thing that could’ve happened to me.

Because when you’re no longer being constantly validated for your lifestyle, you’re forced to confront the question: is this really working for me? Not just emotionally. But practically. Is it growing me? Is it deepening me? Is it connecting me to others in real, reciprocal ways?

When I lived cheap, I thought I was rich. But now that I live expensive, I feel wealthy. And I don’t mean just financially. I mean internally. I’ve built something I trust. I’ve surrounded myself with people who challenge me. I’ve rooted into a place that stretches me. And most importantly, I’ve stopped using my lifestyle as a substitute for identity.

I look back on my time in Thailand with genuine affection. It gave me exactly what I needed at that stage. It offered healing, time, and space to listen to myself. But I also see now how the very things that helped me began to hold me back. And that’s not a contradiction. That’s how life works. What saves you in one season may stunt you in the next.

There’s one more thing I need to say – especially to the digital nomads still out there, still in the early chapters of the journey. Don’t let anyone shame you for starting where it’s cheap. There’s wisdom in building in low-pressure environments. There’s value in making mistakes where the stakes are smaller. But don’t confuse comfort with arrival. And please, don’t confuse separateness with sovereignty.

Because over time, that loneliness I used to feel – the one I wrote about behind the laptop lifestyle – it didn’t go away with better community or slower mornings. It only started to shift when I stopped seeing myself as a guest in someone else’s country. When I stopped measuring life in dollars and started measuring it in alignment.

Now, when I go back to Chiang Mai – which I still do occasionally – I see it with clearer eyes. Not as a paradise or a trap. Just as a place. One that helped shape me, but no longer defines me. And I’m grateful for that.

Some people find themselves by escaping. Others by embedding. For me, it took doing both. But if there’s one thing I know now, it’s this: sometimes growth isn’t about what you leave behind. It’s about where you decide to fully show up.

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