Broke Under the Sun: The Real Reason Freelancers Fail in Thailand.

I remember the day you decided Thailand was going to be your next remote-work paradise. You stood there, brimming with optimism, waving your laptop and chanting, “Digital Nomad!” It all sounded grand at first: blazing sunsets on a sandy beach, friendly locals with that famous Thai smile, and a laptop lifestyle funded by your Western paycheck. But it’s not exactly a fairytale. If you’re counting on easy entry, stable work, and a smooth day-to-day life, let’s just say you might be in for a bumpy ride.

Don't forget the power cord!

Before I dig into the sobering stuff, let me start with why Thailand is often top of the expat bucket list. If you talk to the Thais themselves, they’ll proudly mention the countless Buddhist temples—these graceful architectural wonders scattered across every province. They’ll point out the insanely tasty (and supposedly healthy) cuisine—Som Tum, that zingy papaya salad, or the iconic “Paed Thai.” And of course, they’ll spotlight the country’s legendary warmth toward visitors, exemplified by the “Thai smile.”

But the romance dims if you really peel back the layers. Sure, temples are nice, but if we’re honest, how many times will you actually trudge around them after you’ve posted a few selfies? Maybe if you’re a Western grandma hell-bent on discovering your “inner Buddhist,” you’ll keep going. But watch out for those edgy tattoos of Buddha’s face on your arm—did you know Thailand frowns on them (to put it mildly)? Even something that seems innocent can be cultural heresy.

Then there’s Thai food. It’s often lauded as a healthy blend of veggies, fresh herbs, and bold flavors. The truth is, the version you get on the street might be a watered-down, Western-friendly adaptation. Plus, Thailand has its own share of rampant pesticide usage. Look at how they import grapes from China—coated in even more chemicals—so if you’re a health freak, you’d better break out the soda powder and wash your produce like your life depends on it. Because in this case, it might.

And we can’t forget the “friendliness factor.” Everyone loves to talk about how hospitable Thais are. Walk out of Bangkok’s Suvarnabhumi Airport, though, and you may be greeted by a wily taxi driver trying to rip you off with a sky-high fare. Sure, you can book yourself a cushy airport limo and skip the haggling, but you’ll get the same kind of breakneck driving. If it’s early morning, you might have to poke the chauffeur to keep him from dozing off at the wheel.

So, what keeps foreigners coming back for more? Apart from the beaches with cheap booze—just watch out for broken glass and needles in the shallows—there’s that never-ending pool of attractive, younger romantic prospects. Many women here are open to dating older or less handsome foreigners. You’ll find tales of laborers, truck drivers from the UK who meet a local beauty two decades their junior, only to watch their wallets dwindle at warp speed. Others highlight the easy availability of certain “services,” which are legal in a loose sense—or simply tolerated.

Amid all this, you might be asking, “Whose advice do I trust?” Enter the expat old-timers. These are the guys who’ve been in Thailand for ten, twenty, or thirty years. They’ll happily regale you with their “vast knowledge,” yet it’s worth noting each one lives in a bubble:

• Some folks settle in Pattaya or Phuket. The UK or Russian "Pattaya Man" will tell you the Thais are super laid-back, open to Western culture, and you can wander around in a budget “Chang” beer shirt with zero shame. These guys mostly mingle with a local underclass that caters to them because—drumroll—they have money. Their partners often sport tattoos, wear Western clothes, and earn wages in service jobs of, let’s say, lower or questionable repute.

• Others stake out a claim in the far north, in rural Isaan (Esan) provinces like Nong Khai. The Aussie Nong Khai man, who has lived 30 years in the jungle, could swear everyone up there is bribable and easygoing, and it’s no big deal to keep both a wife and a minor wife under one roof.

• Then there’s the German Bangkok Men, who believe they inhabit the “modern” side of Thai life, where you can rotate new girlfriends with the same frequency you rotate your socks. Eventually, though, old age looms, Sidegra from the MBK Centre's pharmacy replaces youthful vigor, and once the money runs out—poof!—these men vanish back to their home countries.

Ask the Pattaya Man for some serious advice!

All these “I’ve been here forever” types share a few consistent traits: they have minimal formal education, don’t really engage in any high-level professional work, and lack a genuine understanding of Thai society beyond the lower socioeconomic levels. That’s why you’ll often see them utterly baffled at how things work at the higher rungs of business or government. The middle class or upper class in Thailand isn’t exactly rolling out the red carpet for random freelancers from abroad—especially if you barge in expecting them to operate by your Western rules.

This mismatch of norms can lead to big problems, especially when well-intentioned Westerners start preaching about democracy or monarchy, without comprehending how deeply tradition and “conservative values” shape voting and governance in Thailand. Meanwhile, the local media might be broadcasting stories of terrorism in Europe or robberies in France, shaking local heads at the West’s “lost” sense of morality and sense. None of that helps your case if you waltz in loudly criticizing their power structures. No wonder some foreigners end up disillusioned, or in serious trouble if they accidentally offend the monarchy—something that can land you in prison if you’re not careful.

Speaking of prison, let’s talk about that. If you’re into “other substances,” perhaps you’ve heard rumors that you can bribe your way out of any arrest. It’s not entirely untrue, but it’s not the foolproof myth some expats believe. By the time your case hits the courts, you can expect a long, costly process—often ending with you deported anyway, after that multi year sentence in a prison. If that’s your idea of adventure, well, I guess it’s one way to have a story to tell.

Work-wise, Thailand can be even trickier than you think. Many Western employers won’t let you log in from so-called “insecure” countries in Southeast Asia, forcing you to jump through digital hoops with a VPN. But in 2025, it’s not as simple as flicking on NordVPN and calling it a day—major clients increasingly block mainstream VPNs, and your 2FA or MFA apps have a nasty habit of revealing your true location, or perhaps it's the IPv6 configuration you overlooked. Then there’s the focus factor. Picture this: you’re in a nice condo in Bangkok or by the beach, trying to finish code for a client, while the siren call of nightlife and new friends beckons. How many deadlines will you blow before you realize you’re sabotaging your own income?

Of course, there are those shared office spaces in Bangkok where you’ll mingle with other digital nomads, but don’t expect everyone to be a software engineer. You might find more vloggers, bloggers, and “content creators” than you’d see at a YouTuber convention. If you’re looking for deep, intellectually stimulating coworking buddies, you might need to manage those expectations.

Ultimately, if you’re dead set on forging a freelance career in Thailand, you need the odds in your favor. That usually means bringing in your own remote gig from your home country, so you’re not scrabbling for local jobs in an environment that’s not exactly rolling out the red carpet. You’ll also need the right visa—forget those months of “hop in, hop out” tourist visas that keep you in a state of constant dread at immigration checkpoints. And it probably goes without saying that you should avoid the cheerful advice of, say, a 30-year Pattaya Man or some starry-eyed Russian vlogger who found fleeting fame on TikTok.

Let's go visit some temples.

If you can manage to keep your partying in check, refrain from public crusades against the Thai culture or silly Thai habits, and stay strictly on the right side of the law, you might actually find a balance—especially if you can handle living in a condo with solid internet, a discreet but stable routine, and a willingness to shut your mouth when local social customs demand it. Just remember that if you show up at a Thai business-related dinner event, your “bargirl” or “ex-bargirl” girlfriend might not be the best plus-one, you might utterly embarrass your host. Thais can easily see to which class of the society someone belongs to. Some cultural lines remain firmly drawn, even if the nightlife scene seems totally freewheeling.

Btw, did you know you are subject to global Thai taxation if you stay over 180 days per year in Thailand? Yes, dividends and rental income as well. Good luck with that!

All things considered, Thailand can be a land of (imported) opportunity or a vault of disasters, depending on how you navigate it. If you’re sold on the dream, at least go in with your eyes wide open. Thailand is a puzzle of tradition, bureaucracy, exotic appeal, and hidden or obvious pitfalls. Approach it with a dash of humility, a truckload of caution, and a realistic plan for earning your keep. And if something doesn’t feel quite right—whether it’s a sketchy visa agent or an “overnight girlfriend” whose affections might be influenced by your wallet—trust your gut. In the Land of Smiles, not every grin is an invitation to easy living. The more you know, the better prepared you’ll be to avoid the usual traps and maybe, just maybe, carve out that perfect remote-work life you’ve been picturing all along.

Oh, an afterword, before I forget it. You will forget it for sure:

Some of the nomads who land in Thailand get so swept up in the easy sunshine and cheap thrills that they forget that the clock is ticking on pensions and future plans. There’s a certain charm in waking up to ocean views and partying like there’s no tomorrow, until—bam—ten or twenty years disappear in the blink of a hazy neon sign. By the time they shuffle back to their home country, all they’ve got is a suitcase full of sun-drenched stories, a fading “Chang” T-shirt, and not much else. The reality check hits hard when they’re stuck in a dingy social apartment in Manchester, flipping through photos of their old Thai escapades, trying to warm their dreary days with golden memories that don’t exactly pay the rent.

Back home again - rich and famous?