The midlife illusion of freedom: Why some men start over in Asia — and still feel stuck

They say freedom is a plane ticket away.

Sell your things. Quit your job. End the relationship that grew stagnant long ago. Then buy a one-way ticket to Thailand, Vietnam, or some other place with fewer rules, looser expectations, and just enough cultural friction to feel like reinvention. It’s a familiar fantasy, particularly among a certain kind of man—Western, midlife, financially comfortable enough to walk away, but inwardly restless in a way that even success hasn’t cured.

I know that man. I was him.

For years, I moved between Bangkok, Chiang Mai, and Saigon, orbiting Southeast Asia like a satellite trying not to burn up on re-entry. I had all the flexibility I wanted: my income didn’t tie me to a place, I wasn’t accountable to any particular system, and nobody expected anything from me except perhaps the occasional visit back home. On paper, it looked like freedom. But freedom, I’ve come to realise, is easier to wear like a costume than to actually live.

I had spent four years cycling through cities. Back then, it felt like I was gaining momentum, like each new visa stamp brought me closer to something essential. But momentum can be mistaken for growth. In some cases, it’s just the absence of roots. I wasn’t evolving—I was rotating.

Chiang Mai eventually became the place I returned to most often. It had just enough infrastructure to work smoothly, just enough wildness to feel like I was still resisting something. For two years, I lived there more or less full-time. I knew the cafes with the fastest Wi-Fi. I got used to the rhythm of the rainy season. I made friends who, like me, had found a sort of floating community in this quiet northern Thai city—a place where no one ever needed to explain why they had left their old life behind.

There’s a seduction to Chiang Mai. It wraps around you slowly, offering you the illusion of simplicity. You wake up to birdsong instead of traffic. You eat breakfast barefoot on a terrace surrounded by palms. You start to believe you’ve finally opted out of the system. But often, what you’ve really opted out of is intimacy—with others, and with yourself.

The fantasy begins to crack in quiet moments. Not through crisis, but through accumulation. Empty Tuesday afternoons. Dates that feel like performance. Conversations that orbit the same expat clichés. The feeling of living on pause while pretending you’ve pressed play. The sense that even though you’ve bought yourself time, you’ve done so by leasing out meaning.

There was one night in particular that still sticks with me. I was at a bar in the Old City, nursing a beer and listening to a man in his fifties talk about how free he felt. He’d lived in Chiang Mai for seven years. Hadn’t been back home in four. His eyes looked tired in a way that didn’t match his words. He had the language of freedom down—low cost of living, no government overreach, plenty of beautiful women, no pressure. But there was something calcified in the way he told his story. A man who had curated his world so carefully that no one could ever touch him again.

And I wondered, quietly, if I was becoming him.

Back then, I still believed that freedom meant no constraints. That real masculinity was about dominance over time, space, and emotion. But what I really had was avoidance. Avoidance wrapped in the glamorous costume of choice. I could work from anywhere, so I worked everywhere. I could date freely, so I rarely committed. I could leave any time, so I never stayed.

This script of masculinity—provide, perform, pursue—had shaped me without my consent. But it didn’t teach me how to feel, how to receive, or how to be seen. And in places like Chiang Mai, I met countless other men bound by the same blueprint. Men building passive income portfolios they didn’t believe in. Men dating women they didn’t know how to connect with. Men who had replaced the suffocation of the West with a new kind of isolation. A more exotic loneliness, but no less hollow.

I’d always imagined that freedom would feel like expansion. But in practice, it started to feel like I was evaporating.

That’s when I made a different kind of move. One that, from the outside, might have looked like a retreat. I moved to Singapore.

At first, it felt like failure. Like I was giving up. Going conventional. Submitting. Singapore, with its rules and fines and formality, was everything I had once tried to escape. But the longer I stayed, the more I understood what I had been avoiding. Not just boredom or bureaucracy—but intimacy. Accountability. Slowness.

Structure started to feel less like confinement and more like rhythm. The same MRT lines. The same river walks. The same people showing up for me—and expecting me to show up too. I began to realise that the right kind of structure doesn’t trap you. It frees you to actually feel your life.

There’s a different kind of freedom that comes from routine. From having your name on a lease, from building habits, from being known by your neighbours. It’s not flashy. It doesn’t fit in a hashtag. But it holds you.

In Singapore, I had to confront something I’d long denied: that the freedom I’d been chasing was often just an excuse to not belong. Because to belong requires vulnerability. It requires the willingness to be known, not just admired from a distance. And belonging, I realised, isn’t antithetical to masculinity. It may be its highest form.

 

 

 

 

 

 

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A post shared by Justin Brown (@justinrbrown)

There’s a quieter kind of manhood I’m learning to inhabit now. One that doesn’t announce itself. One that doesn’t require external confirmation, doesn’t hinge on dominance, or productivity, or detachment. It’s not flashy. It’s not something you post about. And for a long time, I didn’t recognise it because it didn’t resemble the masculine archetypes I grew up with.

This version of manhood isn’t about constant motion or impressive metrics. It’s about the capacity to stay present. To be reliable, not just available. To listen without needing to fix. To hold space without needing to fill it. It’s about cultivating an inner spaciousness that isn’t dependent on place or circumstance.

That’s what I’d been missing in those years of drifting. I wasn’t afraid of responsibility—I was afraid of being seen carrying it imperfectly. I wasn’t avoiding intimacy—I just didn’t have the tools to sit in the vulnerability it required. And I wasn’t really free—I was just highly mobile. There’s a big difference.

So much of modern masculinity is built on the illusion of control. The idea that if we optimise enough, achieve enough, or remain unattached enough, we’ll be safe from disappointment. But the deeper work has nothing to do with control. It’s about learning to remain open even when things don’t go your way. To stay soft in a world that rewards hardness.

I look around now and see how many men are aching for that shift. Not because they’re weak. But because the old model is tired. It rewards performance but punishes honesty. It tells you to be strong but never tells you what kind. It leaves no room for confusion, or tenderness, or grief.

And grief is part of this too. Grieving the years spent chasing the wrong kind of freedom. Grieving the relationships that didn’t survive our emotional absence. Grieving the versions of ourselves we outgrew but never said goodbye to. That grief doesn’t make you less of a man. If anything, it roots you more deeply in your humanity.

In Singapore, I’ve started to see that freedom isn’t about avoiding these feelings—it’s about having the capacity to stay with them. To let them wash through without running. And that kind of staying takes a different kind of strength. A subtler one. But it’s the kind I trust now.

There are mornings I still miss the chaos. The unknown. The flicker of excitement that comes with new terrain. But I’ve also learned that peace doesn’t mean flatness. It means depth. And the only way to experience depth is to slow down long enough for it to reveal itself.

These days, I wake up in Singapore and walk to the same café. The barista knows my order. The guy at the gym nods in recognition. My routines don’t feel like limitation—they feel like presence. I’m not trying to disappear anymore. I’m trying to be here.

And that’s a very different kind of freedom.

The kind that lets you slow down enough to actually feel your own life. The kind that invites you to stay in the room when things get uncomfortable. The kind that lets you build something—connection, intimacy, contribution—without needing to broadcast it.

It’s easy to confuse movement with transformation. To believe that changing your location will change your life. And in some cases, it can be a catalyst. But without inner shifts, the outer ones are just distraction.

If I could speak to my former self, I wouldn’t tell him not to go. I’d just tell him not to get lost in the going. I’d remind him that the point isn’t to avoid pain or discomfort, but to face it with enough steadiness to be changed by it. And that can happen anywhere—Bangkok, Singapore, or the quiet of your own room.

Freedom, I’ve learned, is not about escape. It’s about presence. It’s about building a life you don’t need to run from. One where your masculinity is measured not by how far you can stretch from commitment, but how deeply you can root into it.

And that kind of life? It takes more courage than a one-way ticket. But it lasts longer too.