And Why Thailand Doesn’t Care
Fear has an interesting relationship with geography.
The Geography of Leaving — Vol. 1
Ask someone why they haven’t left—left the country, left the situation, left the version of their life that stopped fitting somewhere around 2019—and they will give you a list. A very organized, very reasonable-sounding list. The house. The family. The job. The pension. The dog. The idea that somewhere else is somehow less real than right here.
What they won’t say, because most people don’t say the true thing first, is this: they’re scared the grass isn’t actually greener. That they’ll get there and still be themselves. That the problem wasn’t the country.
Valid fear. Wrong conclusion.
Because here’s what the people who actually left will tell you—quietly, from a café in Chiang Mai or a hotel apartment in Dubai or a villa in Ubud that costs less than your car note—the problem was never you. It was the system you were trying to function inside of. And some systems are simply not built for certain people to thrive.
Recognizing that isn’t giving up.
It’s just finally reading the room.
Thailand: The One Everybody’s Talking About
For a while, Thailand was the answer. Warm. Affordable. Welcoming. The kind of place where your dollar stretched so far it almost felt illegal. And for a certain type of person—creative, untethered, done with the performance of American normalcy—it was perfect.
It still is, mostly.
But Thailand has been paying attention.
In May 2026, the Thai government approved plans to end the broad 60-day visa-exemption program that had covered 93 countries and territories and replace it with a shorter, more limited structure. Until the revised rules officially take effect, travelers still need to check the current requirements before booking anything longer than a vacation.
Translation: the era of casually building a long-term life around tourist exemptions is becoming a much less reliable strategy.
Thailand saw what was happening. People were using short-term entry privileges to stay long-term, repeatedly leaving and returning, and constructing entire lives around a system that was never intended to function as residency.
Thailand has apparently decided that if you want to live there, you may eventually have to admit that you live there.
The smarter play for qualifying remote workers may be the Destination Thailand Visa, or DTV. It is valid for five years with multiple entries, but that does not mean you can remain in Thailand continuously for five years. Each entry permits a stay of up to 180 days, with the possibility of one additional extension of up to 180 days.
It’s the long game.
And if you’re serious about being there, it is certainly a more legitimate game than pretending your third border run is just an unusually committed lunch outing.
Bali: Paradise Got a Price Increase
Bali used to be the move.
And in many ways, it still is—the culture, the food, the spiritual reset that happens somewhere between the rice fields and the second cup of Balinese coffee.
But word got out.
Rent, imported food, and general lifestyle expenses in popular expat areas such as Canggu and Seminyak have increased considerably. The continued influx of tourists, remote workers, and longer-term foreign residents has placed pressure on housing in the most sought-after areas.
What was once widely treated as a budget destination has quietly become a mid-range one.
Still cheaper than London. Still beautiful. Still worth it for the right person.
But the days of casually arriving in Canggu and finding a flawless $600-a-month paradise because someone on YouTube did it six years ago?
Gone.
The people who got there first are still loving it.
The people arriving now are doing more math.
So Why Are People Still Scared?
Because leaving is an admission.
It says: this isn’t working for me.
And we have been trained—thoroughly, expensively trained—to treat that admission like failure.
It isn’t.
Leaving is data.
It means you looked at your options, did the actual math, and decided that your quality of life was worth more than your zip code.
That’s not a crisis.
That’s a spreadsheet.
The fear underneath it all is usually about identity. Who are you if you’re not from here, working here, building here, suffering here like everyone else is suffering here and calling it character?
You’re the same person.
Just with better weather. Cheaper rent. And—depending on where you land—a significantly more interesting Thursday night.
I have a friend. Lives in Jomtien, just outside Pattaya, Thailand. Has been there for years. Calls it the best decision he ever made.
He’s very…settled.
Very comfortable.
Very enthusiastic about the local culture in ways that are, let’s say, specific to that particular stretch of coastline.
I’m not here to judge the man.
Thailand is famously open. He is famously appreciative of that openness.
We’ll leave it right there and wish him well.
The point is—he left.
And he’s happy.
Annoyingly, consistently happy.
That’s the data.
Fear of leaving is really just fear of finding out that the life you were promised was optional all along. That you could have chosen differently at any point. That nobody was actually keeping score the way you thought they were.
They weren’t.
The tent is folding.
The question is just whether you’re walking out or waiting to see what falls on you next.
Next in the series: My plan, my timeline, and why Dubai makes more sense than you think.
Stay curious. Stay unfuckable. And… never trust a suitcase with four good wheels.
— Kimberly Ann Hawes
Creator of The Daily Fuckcabulary
© 2026 Kimberly Ann Hawes. All rights reserved
