Working abroad can be thrilling, but it’s rarely simple. From visas to cultural barriers, what starts as an adventure can quickly become an uphill battle. After two decades living across three continents — from London to Dubai to Hong Kong — I’ve learned that some cities make expat life far easier than others.
For me, one city ultimately stood out as the best — and easiest — place to work and live.
My First Expat Leap: London
I was 23 when I left South Africa for London on a working holiday visa. It felt like the dream: I landed a job as a music editor, met the Spice Girls, and even judged the Brit Awards.
But reality set in quickly. The gray skies, cold weather, and isolation hit hard. After just seven months, I quit. The lesson was clear: a glamorous job means little if the environment doesn’t suit your lifestyle.
Building a Career in the Middle East
At 30, I moved to Dubai as an editor, unsure how life would be as a gay man in the UAE. To my surprise, it wasn’t an issue. With 90% of the population being expats, finding community was easy.
Dubai offered safety, efficiency, and opportunity — but it was also relentless. The city demanded constant hustle. After five years, I tried Abu Dhabi, hoping for balance.
But while Abu Dhabi was quieter and family-friendly, it lacked vibrancy for singles like me. A year later, I knew it was time to move on.
Searching for Belonging in Asia
My next stop was Singapore. Famous for safety and order, it never clicked for me. Locals my age mostly lived at home, making friendships difficult. I often escaped to Bali or Thailand on weekends. After six months, I moved again.
Hong Kong seemed promising. At the time, work visas were easy and jobs plentiful. But the pandemic lockdown changed everything. Redundancies spread, costs skyrocketed, and opportunities dried up. The city’s payoff no longer matched the pressure.
Finding My Place in Bangkok
After years of bouncing between cities, I returned to Thailand — but this time, not just as a traveler.
Bangkok turned out to be the easiest city I’ve ever worked in. It has everything expats crave:
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Affordable cost of living compared to other global hubs.
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Exciting lifestyle with vibrant culture, nightlife, and food.
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Flexible visa options, including the new Destination Thailand Visa, designed for freelancers and remote workers.
Applying for the visa online cost me about $310 and granted me five years of stability. For the first time in a decade, I don’t feel the anxiety of looming visa renewals.
Now, I’ve been in Bangkok for nearly a year. I’ve built a balanced routine, work comfortably, and enjoy a lifestyle that feels both sustainable and fulfilling.
The Right City Makes All the Difference
Expat life isn’t just about the job — it’s about the ecosystem you live in. From the struggles of London’s winters to Dubai’s constant grind, I learned that professional success means little if the environment wears you down.
In Bangkok, I’ve found both ease and opportunity. After 20 years of searching, it’s the first place where I feel I can finally breathe.
For now, I’m done looking.
