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Leaving America E6: The Digital Nomad Life - Southeast Asia

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The digital nomad movement has evolved from a fringe lifestyle into a global phenomenon, with Southeast Asia emerging as its undisputed headquarters. This episode explores the realities of remote work in paradise, cutting through Instagram filters to reveal what actually awaits Americans seeking escape through digital nomad visas.

We break down the distinct flavors of nomad life across four key destinations. Bali offers spiritual sanctuary amid rice fields and infinity pools, where $2,000 monthly buys a lifestyle that would cost quintuple in California. Thailand provides both Bangkok's electric energy and Chiang Mai's peaceful mountain retreats, with world-class healthcare. Malaysia quietly delivers perhaps the region's most straightforward digital nomad visa alongside modern infrastructure and multicultural richness. Meanwhile, the Philippines compensates for infrastructure challenges with unmatched friendliness and cultural accessibility for Americans.

Beyond the practical aspects of visas, accommodation, and Wi-Fi speeds, we dive into the deeper emotional journey of disconnecting from American expectations. Expert guests – from long-term digital nomads to immigration specialists – share insights on building community abroad, navigating cultural differences, and handling the inevitable complexities of transient relationships. They address the tension between enjoying paradise and respecting local communities, offering guidance on responsible nomadism that avoids contributing to gentrification.

Featuring:

Chris Dodd 

Tim Marting

David Lesperance

Richard McColl

Chawadee Nualkhair

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Tim Marting:

Citizen Remote is a global mobility company. In essence, we help with visas, taxes, accommodation, insurance. We also have a social community. We have over 20,000 members. Our big thing is understanding the complexity within visas. So obviously we do a lot of everything, but right now we're really niching down on helping people with visas because that's the first part of the process that people encounter when relocating abroad. Obviously, the next year you're going to have to do taxes, so you can use us for that. You're going to have to get insurance up front, so you can use us for that. But visas is quite complex and we essentially have immigration teams on the ground in over 35 different countries and we're growing that number every day.

Shawn:

Welcome to Leaving America, the podcast for people who think remote should describe their job, not their chance of affording a house in the United States. Today's episode is for anyone who's ever read the latest Supreme Court decision, checked the weather in Bali and wondered could I just go? The answer is yes, but not without a little bureaucracy, a grasp of visa nuance and a willingness to change your diet. In this episode, we're going to focus on the digital nomad visa and while many countries are adopting this relatively new visa program Portugal, spain, croatia, estonia, mexico, costa Rica, mauritius, united Arab Emirates, romania, just to name a few today we're going to be looking at Southeast Asia. We'll be discussing the spiritual meccas of wanderlust and work from anywhere Bali and Thailand and we'll also take a look at Malaysia and the Philippines, two countries quietly building their own nomad cred while everyone else's Instagram feed is clogged with Balinese waterfalls and White Lotus filming locations in Thailand. And because you're not just looking for pretty views, you're looking for practical escape routes. We're going to dive into visa options for long-term stays, health care, cost of living, language barriers and the actual lifestyle, because you don't just want to leave America, you want to land somewhere you'll actually like.

Shawn:

I'm your host, shawn C Fettig, and if you've ever thought this would be better with a view of rice patties, you're absolutely in the right place To stay updated on the latest episodes. Follow, like and share Leaving America on the Deep Dive with Shawn podcast feed. Wherever you get your podcasts, and if you've escaped American chaos for island life or are just wondering which is the best VPN to stream Hulu in Bali, drop us a line at deepdivewithshawn at gmailcom. All right, pack your bags. This is Leaving America.

Chris Dodd:

Yeah, so there's a bit of contention on what that actually means that term. For me, the digital part is very self-explanatory. It's just you work online, so there's no real debate on that. The more debatable word in digital nomad is nomad. So at what point do you become a nomad and this is a discussion I've had with lots of people in this community is, if you travel to a different country every month, then you could say that you're a nomad. But what happens if you stay in one of those countries for six months and then you do like three months in one other place and three months in another place, and then you just cycle that every year.

Chris Dodd:

So are you a nomad then? Or some friends that I made when I was in Thailand, like eight years ago, they just ended up staying in Thailand and so they maybe go traveling a month a year like a lot of normal people would. So can we really call them nomads anymore? Or like if a person works a normal job but they take a month off to work remotely somewhere else, like not taking a month off work but take a month away from there in you know, in, in your case, the USA to to work remotely from Mexico, let's say so, are they a digital nomad? So to me, a digital nomad it's. I mean, the easiest way to think of it for me is more of like a vibe, it's more of an attitude. It's number one, you've got to be location independent and then, number two, you've got to be interested in, you know, living out of a suitcase for a period and doing more long-term travel. But where it starts being expat and where it starts going into digital nomad is, you know, it's a bit of a gray area.

Shawn:

That was Chris Dodd, otherwise known as Chris the Freelancer, a front-end web developer and content creator who's been living the digital nomad life since 2015, explaining the friction between the concepts of digital nomadism and remote working. A remote worker is anyone who works away from a centralized office. They could be toiling from a suburban living room, a quiet library or the back of a camper van. They might have a traditional nine-to-five job, just one that doesn't involve breakroom donuts or fluorescent lighting. A digital nomad, on the other hand, is a particular flavor of remote worker the kind who also sold most of their furniture, bought a one-way ticket and hasn't received a jury duty notice in years. Digital nomads use the freedom of remote work to travel, not just for vacation but as a lifestyle. They work from different cities, countries or continents, often stringing together months or years abroad with the help of Wi-Fi, co-working spaces and maybe the occasional visa loophole. Think of it this way All digital nomads are remote workers, but not all remote workers are digital nomads. One is untethered and mobile. The other might still have a mortgage and a favorite local Thai takeout spot. This blurry line between the two has become even blurrier in recent years as more people realize that working from home doesn't always have to mean your own home.

Shawn:

Only about 10 years ago, digital nomads were fringe dwellers of the global economy. You'd meet them sporadically in hostile common rooms, usually in Southeast Asia, wearing linen pants and speaking reverently about passive income. Their stories often involved dropshipping, early-stage crypto or obscure Amazon affiliate schemes that were just successful enough to pay for coconut water and malaria meds. It wasn't really clear if they were grifters, visionaries or just over-committed to the idea of never wearing shoes again.

Shawn:

At that time, the notion that someone could work remotely, permanently, not just on a short sabbatical, was radical. Offices were still king, vpns were temperamental at best and the average employer had all the flexibility of a cinder block. The people who managed to break free web developers, SEO gurus, content marketers, graphic designers were few, often self-employed and willing to sacrifice stability for a hammock and a sense of freedom. Stability for a hammock and a sense of freedom. Then came the platforms. The rise of tools like Slack, zoom, dropbox and Asana in the mid-2010s quietly built the infrastructure that made remote work viable. Co-working spaces popped up in digital nomad hubs like Chiang Mai, bali and Medellin, where you could rent a desk network over cappuccinos and attend lectures. Chris Dodd describes the early days of remote work and digital nomadism.

Chris Dodd:

When I started, I think there was you could say that there was a generation or two before me when I started and so obviously, there were the early pioneers. I think the four hour work week was written in, I believe, 2007. And I read it, I believe, in 2013. And it was like very, you know, cutting edge back then. And so these people that were, or these entrepreneurs that were, working online could, you know, essentially move that, move their operations out of an office and do it remotely. And so the early pioneers, would you know, have the crazy idea of, well, why don't I do a meeting via Skype and I can just be anywhere in the world and do it. And so it was just, it was just like very like, adventurous, cutting edge, like entrepreneurs in the beginning. Then, I guess, freelancing came into that, because as a freelancer, you know you're not tied to an employment contract and if, especially as a developer which I can relate to as one you don't actually need to do any face-to-face work, so it's all with a computer. So you know, you could just like take on a project and then go to whatever country and work remotely from there.

Chris Dodd:

The major shifts that's happened since the early days has been the rise of remote jobs, so you can be both a nine to fiver and someone who is. You could be, theoretically, a digital nomad as well. You could go on to a different country every year, every month, and you could work remotely. You know, even on the same time zone you might have to like if you're working for a US company, you might have to work nights if the time zone demands that. But yeah, you could.

Chris Dodd:

If you have a fully remote job in the US and they allow you to work from other places other than the US, then you could take that job and be a digital nomad. And so now I meet people that are more normal working remotely, if I can say that, whereas nine years ago it was like, oh, you're here working remotely as well, wow, what do you do? And it was a bit more cutting edge back then because, yeah, remote jobs. Really, if you had a remote job in 2016, and we're working from Thailand, where I spent most of 2016, that was pretty crazy. But now that that's not. That's not a crazy idea.

Shawn:

The real tipping point came in 2020. Cue the pandemic a global reset button that sent knowledge workers home, pants became optional, and it forced employers to confront an inconvenient truth Most jobs don't require being in an office. What they require is a laptop, wi-fi and less micromanagement. The remote work revolution wasn't just about flexibility. It sparked a seismic reevaluation of where life could happen, and suddenly living in a New York studio apartment that cost more than a villa in Italy started to look like a bad deal. And politicians around the world started to realize the potential in attracting remote workers to spend their US dollars in their countries without tapping the labor market, creating what has become known as the digital nomad visa. Tim Marting, founder of Citizen Remote, which is a global outfit that helps remote workers and digital nomads resettle in new locations, explains this evolution.

Tim Marting:

With the rise of digital nomad visas, which is what we'll call it it's more along the lines of a remote working visa, but that also varies from country to country there has been an explosion of countries that are seeking longer term tourism, essentially, and that's what happened. That's why a majority of these visas got released. Majority of these visas got released. They got released during the pandemic and it essentially opened up the opportunity for somebody who doesn't have the funds to spend $250,000 to $500,000 on an investment visa, which does give you quicker pathways to citizenship often, but it essentially opened up a realm for somebody who works remotely and COVID, pretty much everyone did. But they work remotely, they have steady income and countries realized, hey, we can get these people to come live in our country and essentially alleviate the burden that you know, the death of tourism during the COVID era created, and so, with that, there's still actually many, many countries are seeing the benefits of these types of visas, these remote working visas, and are implementing them even still after COVID.

Shawn:

According to the 2023 MBO Partners Report, over 17 million Americans identified as digital nomads. That's a 131% increase from pre-pandemic numbers. That figure likely undercounts the long-term travelers and informal workers who forgot to mention that they were working from abroad while on tourist visas, that they were working from abroad while on tourist visas. And now nomadism has splintered into subcultures crypto bros, spiritual healers, solopreneurs, ai prompt engineers, web designers, consultants the list is long and it's growing. But beneath the trendiness, there's a serious shift happening.

Shawn:

The digital nomad life isn't just about escapism anymore. It's become a viable alternative lifestyle, one that challenges the assumptions baked into American life that your worth is measured by your commute, that proximity to a cubicle equals productivity, that homeownership and stress-related ulcers are inevitable milestones. For many, the appeal lies not just in the affordability or the climate, but in a kind of lifestyle autonomy that feels increasingly out of reach in the United States, and the Digital Nomad Visa is almost perfectly designed for people that are either 1 unsure if they want to make a permanent move to a new place, or, 2 priced out of some of the other visa options, such as investment. This is David Lesperance, a leading international tax and immigration advisor and founder of Lesperance Associates, highlighting this.

David Lesperance:

Digital nomad visas are certainly within the reach of middle-class people. When you think of digital nomads, the cliche is you know, a young college graduate with a backpack and a laptop. But basically, if you can remotely work or you don't need to be in a location to make and maintain your wealth, you can move somewhere on a digital nomad visa. So there is the same concepts are there and by using what is available to you, with your particular family history. For example, I have a lot of Jewish clients who can make Aliyah under the law of return to Israel and get an Israeli citizenship. You know, different people have different options to them. So just because they're not, you know, high net worth doesn't mean that they don't have options available to them. So just because they're not high net worth doesn't mean that they don't have options available to them.

Shawn:

Still it's not all. Infinity pools and beachside Zoom calls. The movement has sparked backlash in many places around the world, where locals are grappling with rising rents and overwhelmed infrastructure, as Richard McCall, journalist and host of the podcast Columbia Calling, explains.

Richard McColl:

You come in as a digital nomad prepared to pay $1,000, so upwards of 4 million pesos 4.5 million pesos per month and you are going to price out everyone in the local market, and this is a big issue. This has led to a gentrification of some of the very nice areas in which to live in Medellin, and this has created a huge backlash. I'm not going to lie. There are even people sticking up posters against this gentrification and digital nomads, because a lot of the time they come in, you know, they use Uber, they use Airbnb, they do everything online and really don't even really interact with the local community and where they are they could be anywhere in the world, and this creates a problem because it doesn't feel like they're participating in society, and that is a big problem.

Richard McColl:

And then there's another side to this. Is that Colombia, because of the weak peso that we have and the strong dollar although these things fluctuate and because of the easy access to illicit drugs and, of course, prostitution is legal here. We're getting a lot of tourists who come down for all on nomad visas as well, for extended periods of times, just to participate in the bad things that Colombia has to offer, and so people are lumping together the honest digital nomad or the honest freelancer with these what we would call sex tourists, almost a bit like what occurred in Thailand all those years ago. I guess it's still going on now. And so these all end up being lumped together because they come down with all of this disposable income to splash it around. It does increase prices, it does create conflict and, you know, it's a source for great unrest and well displeasure with incoming foreigners. And the other thing is they all seem to gravitate to one of two areas, let's say in Medellin. So therefore they feel like some sort of gringo gulch.

Shawn:

Some countries have welcomed nomads with open arms and shiny new visa programs. Others have responded with crackdowns and morality clauses. Digital nomads, people moving into new places, can also do their part to ensure that their move into a country, into a region, causes as little disruption to the local economy and housing market as possible. Tim Marting explains some things to consider.

Tim Marting:

And so the ways that we would recommend pursuing, you know, responsible accommodation in a country in which you're relocating to it would be avoiding something like an Airbnb, which can oftentimes displace locals, finding the local rates of talking and understanding what other people are paying in that neighborhood, and then also utilizing local platforms to find accommodation that is fairly priced. And so, you know, there's a lot of ways to kind of go about it, depending on where you're going, but if you talk with locals and you use local applications, a lot of the times they're going to be in the local language, so translate it, but figuring out what the rate is that you should be paying, and then paying that rate, and being stern as well with whoever you're utilizing if it's a real estate agent or something like that to say I'm not going to pay this. It is difficult, though, even with that, because a lot of times, local communities won't really give you preference to relocate there. So I mean it is a growing problem. I don't think that there's an exact, you know, perfect answer for this. It is something that it's really. The only drawback to the rise of these visa categories is okay, you know, you're not taking a local job. You're still getting income from abroad, you're spending locally, you know, promoting businesses.

Tim Marting:

But there is the housing question. So there's a few ways that countries have tackled that. Some have created zones where you can't relocate to, so essentially you can't. I think Portugal floated this idea for a bit. I don't think it's ever actually been or come to fruition, but they were talking about sanctioning off Lisbon and Porto and saying if you want to relocate to Portugal, you'd have to move outside of the major city hubs to where you're essentially moving into a community or an area that doesn't have a thriving population anyways, and so you're not really taking local housing and driving up those prices. So there's not really a one-size-fits-all answer to this. It's definitely a concern, but to do it responsibly, just make sure you kind of have the relevant information something that we can assist with as well to know that you're not paying three times what your neighbor is paying, because that will unfortunately displace locals.

Shawn:

For now. The digital nomad movement rolls on as more people realize that freedom might just look like decent Wi-Fi, warm weather and a bank account that isn't being drained by $14 salads and outdated zoning laws. So let's talk first about Bali. This is the land of barefoot enlightenment, where every smoothie bowl comes with a frangipani and every co-working space smells faintly of sandalwood and ambition. If you've ever searched digital nomad on Pinterest, Bali probably showed up before you finished typing.

Shawn:

It's been the unofficial capital of the remote work revolution since the first MacBook was opened in a beanbag chair in Ubud. Bali's lifestyle appeal is obvious. You can start your day with a sunrise meditation class in Ubud, then hop on your scooter and zip over to a chic café where the iced lattes have activated charcoal and the Wi-Fi speed rivals Palo Alto. By lunch, you're slurping a $3 bowl of Mie Goreng while exchanging crypto tips with a guy from Berlin who swears he's building a platform. For many, this is an idyllic life, but if you're moving there as a digital nomad, you'll still need to set up a functional life that allows you to work in addition to play, Chris Dodd explains.

Chris Dodd:

Some people have a hard time understanding how you could work from Bali, because I'm not sure what the perception is in the USA. But the perception of Bali to Australians is just, you just go there for a vacation. It's kind of like our I don't know Cabo or whatever, tijuana or something, right? Maybe that's not the most accurate example, but like it's kind of like our vacation spot, right? So people are like what you live there and you're productive there. They just it doesn't compute, but in their head they're thinking like of typical vacation locations. So like they're thinking they're going to take their computer out at their villa with a pool right in front of them and and get to work while they're drinking a beer. No, it's a completely similar lifestyle in every city, but it's just changing the location. So, no matter what city I'm in, I'm working from a cafe or a co-working space.

Shawn:

Ubud remains the spiritual heart Lush, slow, artsy, it's perfect for writers and healers. Kangu, on the other hand, is more like a caffeinated, tattooed sibling, where everyone seems to be building a brand and the beach is more backdrop than destination. Seminyak is a little more polished and a little more expensive. Still, you can live quite well for about $1,500 to $2,000 a month, and that includes a stylish villa complete with infinity pool, motorbike rental, meals, out massages, gym membership and enough green juice to bankrupt a Los Angeles juice bar. So if you're interested, let's talk about how to get there. The visas If Bali has a flaw, it's that Indonesia's visa system is less than intuitive. There's no official digital nomad visa yet, but there are a few workarounds that remote workers use, each with their own mix of logic, legality and logistical anxiety. There is the visa on arrival For US citizens. You get 30 days, extendable once for a total of 60 days, so it's obviously ideal for short stays, spontaneous escapes or commitment issues. The B211A visa, or the Social Cultural Visa, is your go-to if you're staying a few months. Technically, it's intended for cultural exchange and business meetings, but it's used, to be honest, by digital nomads. Everywhere You'll lead a local sponsor, and this is easily arranged through visa agents and it gives you 60 days, which is extendable up to 180 days total. The temporary stay permit, or the KITAS, is for longer stays. It requires a job offer, investment or retirement status. So if you're already picturing yourself opening a vegan kombucha co-op, this could be your path, but it involves more paperwork than the previous two visas. Finally, there's the second home visa. This came out in 2022. This is Indonesia's answer to we want your money, but not your resume crowd. To qualify, you have to deposit 2 billion rupiah, which is roughly 130,000 US dollars, into an Indonesian bank account. You won't get a work permit, but you will get a long-term visa. There are whispers of an official digital nomad visa, one that lets you stay for five years without local taxation if you're employed abroad, but as of now, it's still floating in legislative limbo, which is to say, don't hold your breath.

Shawn:

One thing that digital nomads care about, maybe the first and only thing, is internet. The wi-fi in Bali isn't bad anymore, at least not if you know where to go. Ubud and Canggu have co-working spaces with fiber optic speeds, soundproof zoom booths and espresso. These co-working spaces are all over the place, and some of the most popular are Outpost and Dojo. As far as health care goes, bali's private clinics are decent and wildly affordable. If you need a dental cleaning, that's going to cost about $25. To visit a general practitioner is going to cost you about $40. So if you have a minor surfing incident involving a selfie stick in your face, you'll be patched up with antibiotics and a bandage for less than a dinner at Cheesecake Factory. For bigger emergencies, many expats fly to Singapore or Bangkok. They're only a few hours away and they're home to world-class hospitals. It's kind of like a regional healthcare strategy. A popular insurance plan for expats is Safety Wing, which sounds like a Marvel spinoff but actually offers decent international coverage for under $50 a month.

Shawn:

So let's talk a little bit about language and culture. If you've been listening to this series, you know where I stand on learning a local language Try. Just like in most places, you can get by for the most part with English. In the tourist zones in Bali, though, understanding local customs is critical. Balinese Hinduism has a rich, visible spiritual life. Offerings of flowers, incense and rice appear daily on sidewalks, temples and motorbike dashboards. Westerners who stomp through sacred spaces with their acai bowls and TikTok dance routines have, unsurprisingly, prompted backlash In 2023,. The local government even proposed a behavioral guidebook for tourists. So, in short, respect the culture, dress modestly in temples and don't rent a scooter if you can't ride a bicycle.

Shawn:

So Bali is beautiful, breathtakingly so, but it's not immune to the impact of its own popularity. Traffic is abysmal, a three-mile trip can take 45 minutes, infrastructure is uneven, power outages happen, water quality is questionable Don't drink the tap water unless you're eager to lose five pounds in the next day and overdevelopment is a problem. Some parts of Bali are now more concrete than coconut. The quiet island paradise has, in places, become loud and cultural tension is rising. With tourism so deeply embedded in the local economy, there's a love-hate dynamic there. Many locals are gracious and welcoming, but wary of being treated like set dressing in someone else's spiritual awakening. So make sure to consider this. Be respectful.

Chawadee Nualkhair:

Thailand really has it all. It's not just like the white lotus thing where you see beautiful beaches and water and you know countless resorts, but it's also there's another side the lovely people, great food, pretty good weather, if you are okay with humidity, and a very reasonable cost of living compared with the US, especially on the coasts. So I mean Thailand, and also Thailand really wants you here. You know, if you're from abroad and you want to, you know, pull up roots and come to Thailand and start a new life. They're happy to have you. It's not like France, I mean, I'm just imagining, I don't know, but I mean a place like that where they're just like oh, you again. Thailand is like, oh, please come. Thailand is like oh, please come.

Shawn:

That was Chawadee Nualkhair, bangkok-based food writer and journalist specializing in Thailand's street food culture, who was featured in Netflix's Somebody Feed Phil, describing Thailand's approach to digital nomads. If Bali is the spiritual sanctuary of the remote work movement, then Thailand is its global headquarters, a place where digital nomads gather not just to work but to live well for less in a society that is somehow both wildly chaotic and delightfully ordered. You want $1 noodles and a $15 massage Done. You want to befriend a monk on Tuesday and then go clubbing on a rooftop bar on Wednesday? Thailand has you covered. And then go clubbing on a rooftop bar on Wednesday. Thailand has you covered.

Shawn:

But as with all good things, there are layers. Thailand is best enjoyed slowly, with full knowledge of what you're getting into. So let's take a look. First, you have to choose your base, and it's not just a one-size-fits-all situation. Chiang Mai is the darling of the digital nomad world. Nestled in the Northern mountains, it's peaceful, affordable and filled with co-working cafes, leafy temples and digital marketers who claim to only work 10 hours a week. They're lying, but it is charming. And then there's Bangkok. Chawadee Nualkhair describes her

Shawn:

love for the city.

Chawadee Nualkhair:

Every day is truly an adventure, because the thing with Bangkok this is the thing that I just love about Bangkok it's never the same. I'm finding new things every day. I've lived here for a long time and every day I learn something new about this city, that something was hidden from me before or something just turned know, turned up somehow like a mushroom sprouted overnight, because it's a really fast city, bangkok, so things are always coming and going, coming and going it. It never really is the same, and that and, and some people don't like that, but I, I really, I really love it.

Chawadee Nualkhair:

that's one of my favorite things about bangkok um and so the food is is a part of that, because it's kind of a cutthroat kind of scene and you know things are coming at you fast and then they go away. There's a lot of fads. It's just fun to follow and I like the people. Even now, even in a big city like Bangkok, you can find, I mean, the land of smiles. It's not Thailand's not.

Chawadee Nualkhair:

I wouldn't say Thailand isn't exactly the land of smiles really, but you can find kindness, you can find help, you can find nice people everywhere, which is surprising in a big city like this, and that's another thing that I really love about Bangkok and about Thailand in general. People are really really nice outside of Bangkok and I love that. You know, if I go up north a few hours, there's mountains, and if I go down south a few hours, there's the beach and there's different food at each. Yeah, I just love the versatility of it. It's also a nice hub, you know you can go to Vietnam, you can go to China, you can go to Malaysia, indonesia, and it's relatively easy.

Shawn:

Bangkok is the vibrant, electric, overwhelming capital. Bangkok is the vibrant, electric, overwhelming capital. You can work in a skyscraper co-working space during the day and eat grilled squid from a street cart under a neon sign at night. Bangkok is like New York City, with better food and more shrines. And then there are the islands. For the adventurous, sun-soaked soul Koh Lanta, koh Phangan and Koh Samui all have their nomad tribes. Expect intermittent Wi-Fi, barefoot meetings and the occasional monkey stealing your breakfast. Realistically, you can live quite well in Chiang Mai for $1,000 to $1,200 a month. That includes a modern apartment eating out every day. I'm not really recommending that, but it's possible. Scooter rental, gym membership and your share of oat lattes and foot massages. Bangkok might stretch you closer to $1,500 to $2,000 a month, but you'll get urban energy, top-tier healthcare and endless convenience. Need a coconut at 3am? That can happen.

Shawn:

Okay, the visas Thailand's visa game is like playing chess blindfolded Expect half the pieces are labeled in Thai and the rules change every quarter. That said, here are your main options. First, there's the tourist visa and visa exemption. So US citizens get 30 days on arrival, which is extendable to 60 at immigration, or you can apply for a 60-day tourist visa in advance, and that comes with a 30-day extension option, so it's good for a couple of months, but not a long-term solution. Then there's the education visa. Take Thai language, cooking or Muay Thai classes and you'll get a year-long visa. Many nomads use this creatively You're studying during the day and threading your toes through white sand on the beach at night.

Shawn:

If you want to work legally in Thailand for a local company, the business visa is the way. You'll need a sponsoring employer and lots of paperwork. Warning, though Thailand takes illegal work seriously. Even remote work is a legal gray zone, unless you're on the right visa.

Shawn:

The Elite visa is, frankly, for anyone with some money. It costs anywhere from $15,000 to $100,000 US dollars and it gives you 5 to 20 years of residency, depending on how much you pay and airport fast tracks. It's kind of like TSA PreCheck, but for your entire life in Thailand. And then there's the long-term resident visa. This was introduced in 2022, and it's tailored for work from Thailand professionals. It requires a minimum income of $80,000 or $40,000, plus in advanced degree, you have to be working for a well-established foreign company and you have to prove health insurance. It's promising, but it's targeted toward high earners, so in practice, many nomads still use tourist visas and extensions, hopping across borders every few months in a ritual known as the visa run, typically to Laos, malaysia or wherever is cheap and fast. It's not exactly legal, but it is extremely common.

Chawadee Nualkhair:

It's not exactly legal but it is extremely common. Honestly, I find that it's more comfortable here than in the United States, especially when it comes to infrastructure. We all know about the traffic jams and cars are. By the way, cars and wine are like 200 percent more expensive here than in the US. So those are bad things about Thailand because of the tax.

Chawadee Nualkhair:

But I don't drive and I've never had to drive because there's a SkyTrain station five minutes away from my house. There's a subway station down the road. Both are really new, really clean and air conditioned to the gills. It's so air conditioned, it's Arctic in there and they go everywhere in the city. Now there's motorcycle taxis, which are kind of dangerous, I think, but I love them because they're so efficient and fast, and there's regular taxis and there's Grab, which is Thailand's version of Uber.

Chawadee Nualkhair:

I really honestly haven't driven in maybe 15 years and I don't ever feel the need to do it ever, and I think that's great. I live near my hairdresser, I live near the grocery store, I live near the nail salon All the important places store. I live near the nail salon, all the important places. I, you know, I, just I and the internet is great On the whole infrastructure. I find to be. I think Thailand's pretty, like, really comfortable. When I compare it to, like when I visit my friends in New York and I go into the subway, you know it doesn't look that great the subway.

Shawn:

You know it doesn't look that great. As Chawadee Nualkhair explains, public transportation in Thailand, especially in the major cities, is world class. As Chawadee said, you don't need a vehicle to get around easily and efficiently. In fact, a vehicle could slow you down. And as far as the internet goes, thailand knows how to get online. Whether you're deep in the city or tucked away in a jungle bungalow, you can generally count on fast, affordable internet. Chiang Mai, especially, has some of the fastest speeds in the country, and Bangkok's digital infrastructure is on par with any major global city.

Shawn:

Coworking spaces like Punn Space in Chiang Mai or the Hive in Bangkok offer air conditioning which is critical in Thailand, and free coffee. Even cafes are work-friendly. It's not uncommon to see a table of six people each wearing noise-canceling headphones and furiously typing, ignoring each other entirely my kind of socialization, actually. It's also worth mentioning food in Thailand. It can be very adventurous and might be somewhat shocking to an average American. Many people are drawn to Thailand for the food, but if you're a little less willing to try something outside your comfort zone, you'll still do fine in Thailand. Here's Chawati Nwalkar again.

Chawadee Nualkhair:

The street food culture is the easiest way to get into Thai culture. Basically, it's the easiest way to meet Thai people. It's the easiest way to observe Thai people and you know how they eat, how they interact and possibly make friends. So and it's, it's open to everyone. I mean the street food is, the areas are being curtailed more and more by the government, but there's still street food out there and it's kind of like the Thai food 101 of Thai food. There's the noodles, there's pad thai, there's pad see ew, the soup noodles, tzuyu, the soup noodles. I find that these are the easiest things for people to eat.

Chawadee Nualkhair:

I take people on food tours all the time and most of them are Americans, and I usually stop first at fried noodle places, because those are the things that everybody enjoys. Who doesn't like rice? Know noodles, or rice noodles charred a little bit at the bottom with some soy sauce and and, uh, pork or beef or chicken, it's, you know, and some egg, it's, it's delicious. So I I think fried noodles are great. Um, the dough, fried, dough, fritters, I mean. I could just go on and on and on about the food, but what I mean?

Chawadee Nualkhair:

I think the Thai food can be accessible and and user friendly. If you know what you're looking for and you know exactly what dishes. If you do a little research, you know what dishes that you can, you can try. There's also, you know, restaurants in hotels that are very, you know, friendly to people who are trying out Thai food for the first time. But honestly, you know a lot of the expats here. They don't eat Thai food. You can go without eating Thai food. You can eat Georgian food, lebanese, so much Japanese food. The community here is enormous. You can eat French food. So much Italian food it's crazy. Turkish food anything, anything but Thai food. A lot of expats kind of live in a little bubble.

Shawn:

Okay. So what if you have an unexpected bout of spicy noodle-induced collapse? Thai healthcare is enviable. Thailand's private hospitals are excellent, particularly in Bangkok. Facilities like Bumrungrad International Hospital and Bangkok Hospital are internationally accredited and often have English-speaking doctors with US or UK training. You might actually find yourself enjoying a hospital visit, if only for the free juice boxes and the fact that a full workup costs less than your last dentist appointment in Boise. Expat insurance plans are widely available and many people combine local coverage with international plans like Cigna Global or Safety Wing. A doctor's visit may run $20 to $50, and full coverage plans often cost $100 to $200,000 a month. Americans arriving in Thailand will most likely experience some culture shock. That will take some adjustment and getting used to, as Chawadee Nualkhair describes.

Chawadee Nualkhair:

You have to change your mindset a little bit, I think. I mean, I know a lot of expats and there are expats who come here and they fall in love and they stay here forever. And then there are expats who are just basically miserable and counting out the days till they can go back home. And the ones who count out the days so they can go back home expect everything to be like it is in america, and it's not there's. If things don't work the same way, because it's a different country in a different culture and and people act differently and people were brought up differently. So it's. You know, there's different priorities, different way of thinking.

Chawadee Nualkhair:

Th Thailand is slower, for example. It's a slower paced country because it's so hot. Even walking down the street you can't do the New York hustle, go, go, go kind of thing. Believe me, because I've tried to do that. Everyone walks too slow for me on the sidewalk and it drives me nuts, honestly, especially like the four across on the sidewalk. Nuts, honestly, especially like the four across on the sidewalks. But the slower pace is just people acclimating to the heat and me like an idiot walking like so fast. I'm pouring sweat by the time I reach the SkyTrain station or my it's. I'm constantly fighting with the humidity and the and the and the weather even now.

Chawadee Nualkhair:

I moved to. I moved to bangkok in 1995. I've seen a lot of things change. I've lived most of my life here in bangkok now. But this, this walking thing, is something I will never be able to acclimatize myself to, to change my ways. But it's one of the symptoms, I guess, of changing your way of thinking, of being like why are you in a hurry? It's still going to be there. So you know, meetings start a little bit later. Work starts a little bit later If you're the manager of somebody. Be prepared. Thais eat breakfast at the office. There's nothing that you can do about it. Meals are the most important thing in the world to Thai people, so you know you can't have them do anything. Nothing starts until they've eaten breakfast and it has to be at the office. It's just one of the little quirks about office life in Thailand.

Shawn:

Thailand is famously known as the land of smiles. What's less discussed is that those smiles come in at least 13 different varieties, ranging from I'm delighted to I'm furious, but socially obligated to remain polite.

Chawadee Nualkhair:

Here's Chawadee again obligated to remain polite. Here's Chawadee again, and the concept of face, which I think many Americans don't get, is still the ones who've lived here for years and years. Calling somebody out to their face to say they're wrong in a crowded space, or challenging them in a crowded space in the name of the truth or whatever, is not appreciated. Everybody just wants harmony. Everybody just wants everybody to be happy and to like be cool Again. Nobody wants somebody to like be embarrassed and then having to like try to fix it in some way that puts a burden on us, you know. So like ignoring someone's face or, like, you know, causing someone to lose face in that way is not only a problem for the person who lost face, but it's a problem for everybody else and it makes you kind of jerk.

Shawn:

English is widely spoken in Bangkok and Chiang Mai, less so in rural areas or government offices. That said, even a few words of Thai will go a long way. Just learning how to say thank you will earn you goodwill and possibly an extra scoop of rice. Thai culture prizes, respect, calmness and a general sense of not losing your cool. Yelling, arguing or making a scene. All beloved American pastimes are frowned upon here. If you have a problem, smile, take a breath and say mai pen rai, roughly translated as no worries, it's okay, or what can you do? I want to take a minute here to highlight the atmosphere in Thailand specifically for LGBTQ folks. Thailand is widely considered one of the most LGBTQ-friendly countries in Asia, and that reputation is well-earned. Bangkok in particular has a thriving queer nightlife scene, and Chiang Mai is welcoming and low-key. While the country has yet to legalize same-sex marriage, though it's in the works, the social atmosphere is generally tolerant, if not openly celebratory, outside of the most urban areas. Transgender visibility is also high, particularly in entertainment and beauty sectors, though trans rights still do lag behind. The vibe overall is easygoing, layered and endlessly fascinating. While Bali and Thailand get the lion's share of love and Instagram reels, it would be a mistake to ignore the quieter, steadier players in the region. Malaysia and the Philippines have been steadily building digital nomad street cred without the crowds, the yoga cults or the constant sound of someone nearby doing a guided breathwork session.

Shawn:

Let's start with Malaysia. Kuala Lumpur, malaysia's capital, has got the skyline of a megacity, the street food of a hawker center and a public transportation system that makes American cities look like they're still waiting for the horse and buggy to catch on. So ways into Malaysia include the DE Rentau Nomad Pass. Launched in 2022,. This Nomad Pass is a real digital nomad visa, not a cobbled-together workaround. To qualify, you must be a remote worker or freelancer in digital industries, so IT, marketing, content creation, etc. You need to earn at least $24,000 a year and the visa lasts up to 12 months and it is extendable. So that's a legit, low-barrier nomad visa in Southeast Asia.

Shawn:

The cost of living in Malaysia is relatively inexpensive. A modern studio in Kuala Lumpur might cost $500 a month, utilities included. You can get lunch for $2. And public transit is cheap, clean and punctual Three things you can rarely say about anything involving wheels in Southeast Asia. Even upscale neighborhoods like Mount Kiara offer high-rise condos with gyms, pools and enough air conditioning to freeze a horse. So, as far as budgeting for a digital nomad, you'll spend about $1,200 to $1,600 a month for comfort, and less if you're scrappy. Kuala Lumpur also has excellent internet, plenty of co-working spaces check out Common Ground or Work with a queue and a strong cafe culture. You can sip your flat white in a Scandinavian-themed coffee shop while responding to Slack messages, all without a lag. Need to hop on a call with New York or London? No problem. Time zones line up decently with both hemispheres and power outages are rare.

Shawn:

Malaysia's healthcare is a hidden gem. Private hospitals like Prince Court Medical Center are modern. They're well-staffed and surprisingly inexpensive. A checkup might run you about $30-50, and specialist appointments are easy to schedule. There's no three-month waiting list just to be told you're fine but probably should hydrate more. And insurance, sure, get it, but many expats just pay out of pocket and still spend less annually than they would on a single ER visit in the US.

Shawn:

English is widely spoken, especially in urban areas. Signs, menus, doctors and bureaucrats all operate in a bilingual environment. So you won't need to mime your way through a pharmacy visit, unless you just enjoy the performance. Culturally, malaysia is a fascinating mix. Enjoy the performance. Culturally, malaysia is a fascinating mix. Malay, chinese, indian and indigenous influences blend into a complex but welcoming society. It's also predominantly Muslim, meaning modest dress is appreciated, especially outside urban centers, but the atmosphere is largely tolerant and chill. You'll find plenty of bars and nightlife in Kuala Lumpur and Penang. It's not Saudi Arabia, it's just respectful.

Shawn:

Finally, let's talk about the Philippines, which is in many ways the easiest cultural landing pad for Americans in Southeast Asia. English is an official language, american brands are everywhere, the people are friendly, funny and genuinely curious about your story, and not in a trying-to-sell-you-a-bracelet kind of way. And yet it's oddly overlooked by digital nomads, and the reason might be that the Philippines doesn't yet have a formal digital nomad visa. But it compensates by offering one of the most generous tourist visa systems in the region. Us citizens get 30 days on arrival and can extend their stay up to 36 months. Yes, 3 years, as long as you keep renewing, and those renewals are cheap and easy and don't require visa runs. You just pop into a Bureau of Immigration office. For many nomads, this simplicity is a huge win. No visa gymnastics, just slow bureaucracy. There's also the SRRV, the Special Resident Retirees Visa, which is technically for retirees, but some younger applicants can sneak in via the investment option.

Shawn:

You can live comfortably in many places in the Philippines, even in parts of Manila, for $1,000 to $1,400 a month. That includes housing, food, transportation and some degree of social life, though if you're an introvert you might find yourself over-socialized here, filipinos are famously outgoing and may adopt you within days. Housing ranges from very basic at $300 a month to full-on, resort-adjacent condos with ocean views at about $900 a month. And yes, those are real prices, so don't feel like it's a scam if you see it. Okay, but the internet? Let's be honest. The internet here is better than it used to be, but it's still not great. The major cities like Manila have decent speeds, but the rural areas are dicey. Fiber internet is spreading slowly, like really slowly. That said, major providers like PLDT and Globe offer decent home plans and many condos come pre-wired. Coworking spaces are still emerging, but you can find them in the main cities. Some nomads keep backup SIM cards and mobile data dongles just in case. It's not romantic, but neither is losing connection during a client call.

Shawn:

Healthcare in the Philippines is not bad for the price. Big cities have good private hospitals with English-speaking doctors, clinics in smaller towns, not quite Mayo Clinic but functional. Private insurance is available and it's cheap. Many just pay cash for routine visits. There's also a national insurance program, philhealth, which foreigners can technically join if they become residents. Still, for anything serious, many expats fly to Thailand or Malaysia, which says a lot Culturally.

Shawn:

It's jarring how familiar the Philippines feels to Americans. Filipinos grow up watching American TV, eating fast food and speaking English. But where Americans bring anxiety and lawsuits, filipinos bring laughter and coconut rice. Expect to be called sir or ma'am with disarming sincerity. Expect karaoke at inopportune moments, which for me is any moment. Expect to be invited to birthdays by people you literally just met, but also expect resilience. The country's been through colonization, typhoons, political turmoil and still manages to laugh more than any place you've ever been.

Shawn:

Okay, those are the four countries in Southeast Asia that offer some great opportunities to work as a digital nomad, but there are two other things that I. Some great opportunities to work as a digital nomad, but there are two other things that I think are important to talk about, things that are probably top of mind for most considering a move abroad, regardless of where they're going. The first is safety. Petty theft in Southeast Asia exists Phones lifted from pockets, bags snatched from scooters. But let's be real. If you've ever walked alone at night in downtown Miami, you already know how to keep your wits about you. Thailand and Malaysia feel especially safe. Bali has some theft, mostly opportunistic.

Shawn:

The Philippines warm people, but some areas, especially Mindanao, are best avoided due to political conflict. Stick to the main islands and tourist-friendly zones. Most of the real dangers come not from crime, but from scooters, dogs and your own overconfidence. Natural disasters are also a thing to consider. This is Southeast Asia. Things move, rain falls, sometimes volcanoes get twitchy. Here's the short list Typhoons in the Philippines, mostly between June and October. Earthquakes in Indonesia yes, including Bali. Flooding in Thailand and Malaysia, especially during rainy season. Occasional eruptions of nationalism, mostly metaphorical, occasionally not.

Shawn:

The solution is to have a plan, know where the embassy is, keep copies of your documents and if you live in a tsunami zone, maybe don't sleep at sea level. The other thing to talk about here not specific to Southeast Asia, but important is if you're considering a move abroad. The fantasy goes something like this Move to a tropical country, find a tribe of like-minded wanderers, develop a six-pack without trying and fall in love with a tattooed barista named Luca. But the reality you may spend your first weeks alone watching lizards on the ceiling and wondering why your phone only lights up for two-factor authentication requests. Yes, there's a huge digital nomad community out there, but it's transient, fragmented and sometimes a bit performative. It's like dating apps lots of surface connections, not always depth. You'll meet people, for sure, but real connection takes time, and time gets slippery when people are always coming and going. You make a friend. They moved into Nang. You start dating. They're on a visa run. You plan a hike, they're suddenly in a 10-day silent retreat. Chris Dodd has had some similar experiences.

Chris Dodd:

Well see, this is the thing it's like. That's part of the. So that's part of the decision on where you go to is how easy it is going to be to meet people. It's more challenging for me to meet people back in my home city than in this community, because people are looking to meet people in this community and so if you travel to the typical places where there's full of foreigners or digital nomads, it's very easy to meet people Now to build long lasting friendships or connections. Some people struggle because, as easy as it is to meet these people, they might leave or it might not be easy to build that relationship with them because you're not stuck together for a long period of time, and that is a downside to a lot of people.

Chris Dodd:

I remember speaking to someone when I was in I won't say names, but I have a friend in Sao Paulo who used to tell me that he enjoyed being in the one place and just having his four friends and that was his life, you know.

Chris Dodd:

And then he had consistency with his friend group. I like having consistency with my friend group, but I also want to meet new people all the time, like. I'm very much about expanding my network, expanding my social circle. I like to constantly meet new people. So the pro and con of that, like the yin and yang of that, I actually would value a bit more of meeting people, and I'm happy to sacrifice the fact that you know they might leave or we're not going to be in the same city all year round. So, yeah, if you're wanting to live this lifestyle and you worry about meeting people, you just simply go to the hotspots and plug in with the community, either via WhatsApp chats or go to a popular co-working space or literally go to talks and meetups that people have planned, and there's so many community initiatives for digital nomads around the world. You just got to go to the right destinations and it's super easy to meet people.

Shawn:

Despite all of this, you can find community, but it won't always look how you expect. In Chiang Mai, you might find it in a co-working space where no one talks for the first week, but eventually someone invites you to a night market and everything changes. In Bali, it might be a breathwork class where everyone sobs in unison and then grabs coffee like nothing happened. I make light of this because I've been in this exact situation In Kuala Lumpur. You'll meet other expats at trivia night who are more stable than they let on, and in the Philippines it might be your neighbor who brings you mangoes and advice in the same breath. Swati Nawalkar describes how Americans can meet people, make friends and build community in Thailand.

Chawadee Nualkhair:

It's not easy at first, it is daunting. You know the way I did. It was by, you know, going to work and working in a Thai office. But if you don't have that luxury then you're you know, you're going to have to do it through hobbies like yoga or paddleboarding, through the women's clubs. Ironically, the American Women's Club is a way that a lot of Thai women get to meet American women and so there's like a cultural exchange that way, because they're the Thai spouses of American husbands. I mean it's the way anybody has to meet people in a big city, I suppose by having a similar interest. I mean I found myself a couple of months ago going to this pottery painting class, like like I mean anyone who knows me would know. I mean I suck, I'm terrible at it. It's like you know watching like a moose, like try to slap paint on, like you know, a garage door or something.

Chawadee Nualkhair:

But you know I was doing it because somebody you know, a new friend, had invited me and it was just something that I feel like I had to do, but it's. You know, you just find yourself doing all these, all these strange things in the name, in the pursuit of friendship, and I think that it's the same all over the world cooking classes, whatnot. There's a thing called the science society, where people go on trips together and all over the country and talk about, you know, arcane stuff like well, it's not arcane, but talk about like highbrow stuff, like textiles and architecture, and blah, blah, blah, mean there's, there's something for everybody. If you look hard enough, there's even a roller derby. I mean, I never would have thought about that. But there's also like a kind of version of, like the rest, like the wwf. I think this is the same everywhere. Um, that you just have to kind of extend yourself a little bit, at least at the beginning, especially if you don't have the luxury of work or school to call back on.

Shawn:

True community usually shows up slowly through repetition and small rituals the same cafe each morning, the familiar face at the gym, the local cashier who starts asking how your day was. Be patient, say yes and be proactive. Offer help, introduce yourself and consider staying still long enough to be remembered. If you're only in one place, one time, nobody will get to know you. The emotional journey of being a digital nomad is not a linear ascent into happiness. It's a wobbly path paved with new friendships, small humiliations, big wins and an almost religious appreciation for working plumbing. You will change. That's the deal. Whether it's for a few months or a few years, you'll learn to live differently and that's worth something, even if you do still miss Trader Joe's. Okay, so, after discussing these options Bali, thailand, malaysia and the Philippines let's say you're standing at your metaphorical departure gate, carry on in hand and wondering which of these great options is for me. So let's make this really easy. If you want smooth bureaucracy, a legit remote work, visa, diverse food and solid healthcare, malaysia might be your best option. It's best for planners, introverts and budget-conscious remote workers. It's slightly less Instagrammable, yes, but far more livable, and the bonus is you'll never be far from curry. If you want tropical lifestyle, surf, spirituality and an absurd number of Australians named Blake or Chris Dodd, bali might be for you. It's best for wellness junkies, creatives, yogis and crypto bros with man buns. It's beautiful and chaotic, but bring patience for traffic and a sturdy scooter helmet. If you want vibrant city life, street food, co-working, utopia and a spiritual side quest, consider Thailand. It's best for first-time nomads, long-haul remote workers and people who think they'll only stay six months and end up staying six years. Go to Bangkok for big city buzz and Chiang Mai for peace and pad thai. And finally, if you want a western adjacent vibe, friendly locals and the ability to get your feelings out at karaoke, the Philippines is calling you. It's best for extroverts, english-only speakers and anyone who's still emotionally attached to Costco. The infrastructure isn't perfect, but you'll feel like you belong within a week.

Shawn:

Imagine your future self six months or maybe a year from now. You've figured out how to extend your visa without tearing your hair out. You know which street stall has the best noodles. You've made a couple friends. You've lost your fear of small dogs and large insects. You've remembered what it feels like to not be exhausted all the time. And even if you go back to the US. Someday, you'll go back changed, because you'll know that the world didn't end when you left. In fact, it began. If this episode sparked something in you a question, a plan, a passive-aggressive conversation with your boss about remote work then stick around, because in next week's episode my husband Pavel, returns to the pod and we talk to some of our friends, Heidi and Tony, who ended up unexpectedly living in the Philippines, about their experience, what they loved, what they didn't love if they'd go back, and much, much more. This is Leaving America, because sometimes home isn't where you started. Thank you.

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Shawn C. Fettig

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