Deep Dive with Shawn

Leaving America E1: Should You Stay or Should You Go?

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What if you could escape the endless news cycle, afford healthcare without a second mortgage, and actually use your vacation days without guilt? Welcome to "Leaving America," the limited series where we're diving into why a record 40% of Americans are now considering life beyond US borders, why so many are actually taking the leap, where to go, and how to get there.

This isn't just daydreaming anymore. From Mexico granting 11,000+ residencies to Americans in 2022 to Portugal's exploding expat communities, the exodus is real. But why now? What's changed to make millions reconsider what was once unthinkable?

In this first episode, we're taking you inside the political exhaustion driving many to seek more stable democracies, where election cycles don't feel like existential threats. You'll hear shocking financial comparisons – like trading a $900,000 Los Angeles home for a $200,000 Portuguese villa, or swapping a $3,500 New York apartment for a $500 Mexican casa. And the healthcare reality? That $18,865 American childbirth versus virtually free delivery in countries with universal coverage speaks volumes.

Through conversations with immigration attorneys, tax experts, and Americans who've already made the move, we examine the stark differences in work culture, community connection, and overall quality of life. As one expat puts it: "It's the best opportunity to reinvent yourself outside the Witness Protection Program."

But we don't sugarcoat the challenges either – from navigating visa requirements to understanding that yes, the IRS still wants its cut no matter where you live. This isn't Emily in Paris; it's real life, just somewhere else.

Whether you're seriously planning your escape or just curious about what's driving this modern American migration, subscribe now to explore whether leaving might actually be the most patriotic thing you could do – voting with your feet for the life you deserve.

Featuring:

Karen McCann

Daniel Tostado 

Matt Wilson

Adrian Leeds

Aaron Martin

Tim Leffel

Xanthe and Dana 

Heather Mason

David Lesperance 

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Email: deepdivewithshawn@gmail.com

Music:
Majestic Earth - Joystock



Shawn:

Welcome to Leaving America, the limited podcast series where we're going to ask the increasingly reasonable question should I sell everything I own and move somewhere? My blood pressure won't spike every time I check the news. This series is for anyone who's flirted with the idea of moving abroad maybe to sip wine in an Italian village, maybe to answer emails from a hammock in Costa Rica, or maybe just a grocery shop somewhere that doesn't involve tactical gear. Over the course of this series, we're diving deep into why more Americans than ever are looking beyond US borders, exploring the legal logistics, the emotional roller coaster, the financial realities and sometimes the mountains of paperwork that can either make you cry or drink, or both. Leaving isn't simple. This isn't Emily in Paris, where you land a perfect job, get off the plane and are perfectly integrated into Paris with no ongoing residency questions. It's more like forms, visa fees, culture shock and learning the hard way that not everywhere accepts your credit card. But there's good news too. There are real opportunities, real paths to build a better, calmer, healthier life abroad. Places where you don't have to mortgage your house to afford a doctor's visit. Places where the work-life balance isn't just a myth. Places where you don't have to wonder if the next election cycle will determine the fate of the republic. And millions of Americans have done and are doing it, and they're not all millionaires, they're not all single and childless and they're not all retired.

Shawn:

Throughout this series, you'll hear from about 20 experts and expats, immigration lawyers, tax professionals, relocation specialists, bloggers, writers, podcasters and people who've actually packed up their lives and made the leap. And today, in this very first episode, we're starting with the big question Should you stay or should you go? And, just as importantly, why are so many Americans even considering this at all? Right now, I'm your host, Shawn C Fettig, and if you've ever stared out the window during a work meeting and wondered would life be better if I were watching dolphins play off the coast of New Zealand, you're absolutely in the right place To make sure you're always notified when a new episode comes out. Please find, follow and like Leaving America on the Deep Dive with Shawn podcast feed anywhere you get your podcasts, and if you have any personal Leaving America experiences, thoughts or questions, please write to us at deepdivewithshawn at gmailcom. All right, pack your bags. This is Leaving America.

Karen McCann:

A lot of people that I talk to are a little bit nervous about moving abroad and they think that it's going to be extremely difficult. It's not really that difficult. There's an awful lot of paperwork which is tedious, but it is also the most incredible experience to live in a foreign culture. It is the best opportunity you have to reinvent yourself. Outside the Witness Protection Program. You get to hit the reset button on your life and your social life in particular, because everybody else in the expat community is just like you. They're new, they're looking to make friends, they've got interesting experiences, they've lived all over the world. They've lived all over the world, they're from all over the world. So you have an opportunity to enrich your life in a way that few people do. And if you have the opportunity and you're serious about it, I wouldn't be afraid. I think, just commit, do it, have a wonderful time. And you know what? If it doesn't work out, you can always move back, have a wonderful time.

Shawn:

And you know what? If it doesn't work out, you can always move back. That was Karen McCann, creator of the Enjoy Living Abroad blog and author of several books, like the Great Mediterranean Comfort Food Tour and Adventures of a Railway Nomad. If you've spent even a minute scrolling real estate listings in Portugal, mexico, france or New Zealand daydreaming about a little stone cottage, a slower pace, a life with fewer breaking news alerts, you are very much not alone. And this isn't just a passing daydream anymore. According to a 2023 Gallup poll, 40% of Americans said they would consider leaving the US permanently if given the opportunity. That's nearly double the number from 20 years ago. And it's not just would consider it someday. It's turning into actual action.

Shawn:

The US State Department estimated back in 2019 that around 9 million Americans were living abroad. That number has almost certainly climbed since then. After a global pandemic, two turbulent election cycles, rising costs, mass shootings and an increasingly strained healthcare system, residency applications from Americans have exploded in countries like Portugal, spain and Mexico. Mexico, in particular, granted over 11,000 temporary or permanent residencies to Americans in 2022 alone more than any other nationality. In cities like Merida, san Miguel de Allende and Mexico City, american expat communities are thriving, full of people who traded high rents, long commutes and astronomical healthcare costs for slower, more affordable, more livable lifestyles. Even Canada, historically selective when it comes to immigration, is seeing a rise in American applicants.

Shawn:

What used to be a joke after every election I'm moving to Canada is now a very real option. People are researching, planning and pursuing. So what's going on? What's changed? Why are so many Americans even those who never thought they'd leave wondering if life might actually be better elsewhere? The answer isn't simple, but the main drivers are clear. They have to do with our politics and our safety, cost of living and work-life balance. In short, people aren't just asking what if I left anymore. They're starting to ask why am I staying? And that's a shift worth paying attention to.

Shawn:

Politics have always been divisive in America. That's not new. What is new is the sheer intensity of the division, the sense that we're not just debating politics anymore. We're fighting over the very definition of reality. A 2022 Pew Research Center study found that 72% of Americans believe the country is more politically divided now than at any point since the Civil War. That's not just wow. People are really passionate lately. That's more like should I be stockpiling food and learning how to knit, and it's not just how divided we are, it's how dangerous that division feels.

Shawn:

The Carnegie Endowment for International Peace officially classified the United States as a backsliding democracy, a term that's usually reserved for countries that are not known for their thriving free press and orderly elections. It's not just theory either. Every time there's an election, interest in moving abroad spikes, but since Donald Trump's re-election in November, it's not just a few dramatic social media posts anymore. It's actual moves, actual visa applications, actual people leaving, and the fear is bipartisan Progressives, particularly women, lgbtq plus folks and people of color, are increasingly worried about safety, rights and even basic dignity. This is Daniel Tostado, an immigration lawyer who helps people relocate and settle in France, explaining how the current American political environment makes France an attractive relocation option.

Daniel Tostado:

Political environment makes France an attractive relocation option For LGBT folks. I think of the fact that Donald J Trump, the president, is trying to remove the X marker on passports in terms of gender, that is now only going to say M and F and that's only based off of what appeared on one's birth certificate, regardless of any kind of medical transition or otherwise. And when France saw that, france reacted by saying that's not how France treats LGBT folks, that how one identifies can be requested to be recognized by the French authorities, and then they'll do so. So I find that France is friendly in that manner. In a similar vein, when we think about women and France and women's rights, that under the US Supreme Court, which currently isa, conservative tilt six justices appointed by conservative presidents, three by progressive presidents that when they revoked Roe v Wade, france's reaction to that was to constitutionalize the right to get an abortion. So I think a lot of the ways in which the US is going, that France is trying to secure the route so that that doesn't happen in France.

Shawn:

Meanwhile, many conservatives are feeling disillusioned too, seeing cultural shifts they view as unrecognizable or feeling like the country is leaving them behind. And a lot of moderates are just exhausted, trying to find some quiet corner of the world where every conversation doesn't feel like a political minefield. No matter where people fall on the political spectrum, the mood is eerily similar Disillusionment, frustration, fear and a creeping sense that things might not probably won't, get better anytime soon, and that's leading many to take a serious look at countries perceived as more stable, more democratic and, frankly, less stressful Countries like Canada, with strong democratic institutions and progressive policies. Portugal, which is politically stable, affordable and fiercely protective of civil rights, and New Zealand, known for transparency, low corruption and a powerful social contract. This is Aaron Martin, principal lawyer at New Zealand Immigration Law, with decades of experience helping people transition to New Zealand, explaining one way in which the country has built and maintained a strong social contract.

Aaron Martin:

We actually have removed the ability for a person to sue another person for personal injury by accident. So if I'm, for example, driving my car and I accidentally knock over a person on a bicycle, that person's injuries, the hospital treatment, the rehabilitation treatment, will be taken care of by this scheme known as the accident compensation scheme. That person can't sue me for loss of earnings. Why? Because the accident compensation scheme replaces 80% of their pre-accident earnings while they're unable to go to work, and so it was established in 1972, if I remember rightly, and it was affectionately known as the Great Social Contract. Established in 1972, if I remember rightly, and it was affectionately known as the Great Social Contract where the people of New Zealand gave up this right to sue people for loss of earnings, for injury, for medical treatment, and that was taken over by the government, and we all pay into the accident compensation scheme when we register our car through our pay. Employers contribute to that, and it covers a wide range of things that people don't expect.

Aaron Martin:

In this particular situation, my client was visiting their sister In the house. There was a door that led down to a basement. In the middle of the night, thinking that this was the bathroom, they went through that door and actually it was the door down into the basement, and they fell down the stairs, suffered a back injury, were hospitalized, had several months where they were, you know, unable to really do anything other than go through rehabilitation, etc. All of those costs were covered by accident compensation, even though that person was visiting here from another country, here from another country.

Shawn:

Even smaller countries like Uruguay, iceland and Finland are drawing attention Places where democracy feels healthy, civil discourse is still a thing and kids don't have to endure active shooter drills. The bottom line is that more Americans than ever aren't just questioning who's in office. They're questioning whether the whole system still works for them, and increasingly, the answer is no. Of course, political drama isn't the only thing sending Americans to Google phrases like cheap countries to live in. Another major factor is money, because in America right now, it feels like, unless you were born into tech wealth, your best bet for financial security is winning the lottery and marrying rich, and I mean both. Housing is out of control, healthcare costs astronomical, education is budget busting and childcare can cost more than a mortgage and wages Not growing. Over the past 20 years, the cost of living has soared, while incomes, especially middle-class incomes, have stagnated. A recent study by the Princeton Review found that over 60% of millennials in Gen Z believe they will never be able to afford a home. This isn't just pessimism, it's math.

Shawn:

In Los Angeles, the median home price is around $900,000, which is about 12 times the median income In San Francisco. The median price is $1.3 million In New York City. Good luck finding a one-bedroom for under $3,500 a month. And it's not just the big cities anymore. Places like Austin, boise and even mid-sized towns across the country have seen massive real estate spikes pricing out locals. Compared to previous generations, it's a nightmare. In the 1970s, a home cost about two and a half times the median household income. Today it's six to 10 times that. And even if you do somehow manage to scrape together enough for a home, there are still towering property taxes, maintenance costs, massive mortgage interest rates and endless upkeep.

Shawn:

So no wonder people are looking elsewhere, because when you compare US housing prices to housing abroad, the difference really is jaw-dropping. In Portugal, you can still buy a charming home in the countryside for under $200,000, a price that might get you a parking space in San Francisco. Even in Lisbon, a modern one-bedroom can be found for under $250,000 to $300,000. And in Mexico, in cities like Merida, oaxaca or San Miguel de Allende, you can rent a spacious two-bedroom house for $500 to $700 a month, and buying a home $150,000 might get you something stunning. This is Matt Wilson, co-founder of Under 30 Experiences and author of the Millennial Travel Guidebook Escape More, spend Less and Make Travel a Priority in your Life. Explaining the difference in cost of living and lifestyle between New York and Costa Rica.

Matt Wilson:

I don't know how I lived on $36,000 a year in New York City, but I remember my business was kicking off about three grand a month in 2012, that I received a salary, I had a business partner and we had some part-time employees and you have expenses, etc. And we had some part-time employees and you have expenses, et cetera. So we had a six-figure business going, but we were only taking $36,000 a year and I realized very quickly that, okay, get rid of this apartment. At the time it was $3,200 a month. I had a roommate. I was splitting it with another guy who was also in his 20s a month. I had a roommate, I was splitting it with another guy who was also in his 20s, and so for that kind of rent, of course you can.

Matt Wilson:

My first apartment in Costa Rica was $250 a month, going to the local farmer's market and really eating like the locals who I mean, if you're making $36,000, but you are going to live like the locals live, and I really made a honest attempt at that. Like I explained before, I was eating rice and beans and the local produce and everything that they would find at the local farmer's market and I lived like a king, right, I paid off my student loans that way and, yeah, quickly I moved up to the $400 apartment and that had two bedrooms, I had air conditioning and I even had hot water on most days, like it was. I was really living then.

Shawn:

In Chiang Mai, thailand, you can rent a sleek, modern apartment for $400 a month and eat incredible meals for $2 to $3. In Medellin, colombia, a luxury, high-rise apartment with a mountain view can cost under $1,000 a month. And yes, you can still buy an actual house on an actual Greek island for under $150,000. Even France has a lower cost of living than the United States. You might recognize this next voice. Adrienne Leeds is the owner of the Adrienne Leeds Group, which offers real estate services to people relocating to France, and she's often featured on episodes of House Hunters International. Here she is explaining how the French cost of living stacks up against the United States. Here she is explaining how the French cost of living stacks up against the United States.

Adrian Leeds:

I know you see me laughing that is because you can live here for half of what it costs you to live in the United States. Half the cost of living in the United States is absolutely insane and ridiculous. And even though France is considered a highly taxed society, the taxes are mostly imposed on the people who are working here on their income. Okay, so retirees, for example, aren't going to pay any income tax whatsoever on their US earnings or pensions or their dividends. But the cost of living is so greatly reduced because Americans pay property taxes that are about 10 times what they are in France. Americans live in mostly suburbia where they have to have cars.

Adrian Leeds:

Ownership and operation of cars is a very expensive ordeal. Aaa will tell you it's $12,000 to $13,000 a year to own and operate a car. You live in an urban area in France. You don't have to have a car because public transportation is fabulous. Right, general costs like internet, tv, telephone in the US on the average about 200 a month, in France 35 euros a month. You start to compare these things. Talk about health insurance. Healthcare costs are 10 times in the US what they are in France. It's literally one-tenth the cost. And healthcare is covered in France up to 70%. So a retiree can come from the US andS and come to France and cost them almost nothing for the health care coverage the rest of their lives. So you know, I tell my clients all the time that a couple can exist very, very well in France on 5,000 euros a month. Live like kings, amazing.

Shawn:

Amazing in New York when you could own an entire house in Portugal for less than that. Why stay in a country where wages don't keep up with inflation when you could build a better financial future abroad? And it's not just an individual issue, it's a systemic one. The US economy has been structured in a way that prioritizes corporate profits over worker wages, making it harder for middle-class Americans to get ahead, save for the future or achieve financial independence or even happiness. Here's Adrienne Leeds again explaining a fundamental difference between France and the United States in this regard.

Adrian Leeds:

I think that capitalism is destroying America and killing the people because they don't understand how important it is for everyone to be happy, not just the wealthy, so this is a big thing for me. I like the fact that relationships matter a lot more than money all the time, because one of the things that you notice when you live here is when you go to the boulangerie. Your boulanger will remember what kind of a baguette you like and create a relationship with you. You're not just a number or a name, whereas in the States they don't care about you. They just want to know how much money they're making off of you.

Adrian Leeds:

It's not the same thing, they're not building a relationship, and it really makes you feel like you're a part of the community and that's a big deal and it's subtle. You don't really notice it at first and then after a while you realize oh, at the cafe he knows I always want my, what kind of coffee I'm going to order, and it just comes without asking for it, things like that. And that just never happens in the States.

Shawn:

The numbers don't lie. If you're a middle-class earner in the United States, the American dream feels less like a dream and more like a very expensive fantasy. And when you realize you could live better for less somewhere else, it's hard not to wonder why keep fighting an uphill battle when there are places where the hill isn't quite so steep. All right, let's rip off the band-aid. Health care, the ultimate anxiety-inducing factor for a lot of Americans considering a move abroad. Because here's the sad truth In the United States, a single hospital stay can financially wreck you, even if you have what's considered good insurance. The costs are staggering. The average price of an emergency room visit is $2,600, and that's before any tests, scans or treatments. Giving birth a routine uncomplicated delivery averages around $18,865 with insurance. And if you need an appendectomy, that can run you anywhere from $15,000 to $50,000, depending on which zip code your appendix resides in. Americans routinely pay 3 to 10 times more for prescription drugs than people in other developed nations. Even basic medications like insulin, which cost around $7 per vial in Germany, can cost nearly $100 per vial in the United States. And this isn't just about a few unlucky people. Over half of all bankruptcies in America are linked to medical debt, Half In the wealthiest country on earth.

Shawn:

Meanwhile, in other countries it's a different universe. In France, doctor visits cost about $27, hospital stays are heavily subsidized and prescription meds are heavily discounted. In Germany, universal coverage. Even freelancers and expats are included. A standard doctor visit is free or carries a very minimal fee. In Spain, legal residents enjoy free public health care and even if you're paying cash out of pocket, most doctor visits are around $50 to $70. Canada also universal coverage, no deductibles, no co-pays. You break your leg, you go to the hospital, you get it fixed, you leave, that's it. Even countries like Portugal, new Zealand and Thailand offer high quality health care at a fraction of the US cost, with far fewer horror stories about surprise bills and financial ruin. Here's Aaron Martin again explaining the New Zealand health care system and his own personal experience.

Aaron Martin:

So we have a government funded health care system where you get your treatment through government hospitals. Through government hospitals you have your own private GP, but often there are subsidised fees to encourage people to go to the doctor. So, for example, you might have government subsidising the fees for a GP visit for children or for elderly. For example, when you are a resident visa holder, you get full access to publicly funded health services. So if you need cancer treatment, if you need something done for your eyes, if you need some form of elective surgery, things of that nature, it is usually done on referral by your general practitioner into publicly funded hospital services.

Aaron Martin:

Now, as with most publicly funded health services around the globe, it means there is a large level of demand, and so you know you will encounter waiting times to get treatment. So it is possible, for example, for people to carry their own private health care insurance, which is certainly not at the eye watering levels that people in the US experience, where they might take, for example, a policy that gives them the ability to have elective surgery done through private hospitals in New Zealand. But by far the majority of New Zealanders will usually rely on government-funded health services and maybe have some form of backup medical insurance to partially cover them for some aspects of their health care. Publicly funded health services, from my experience, are particularly good. If treatment is needed urgently, you usually get treated urgently. I'll give you a personal example. I had a run-in with cancer just after my 41st birthday and I got the result through the publicly funded health system because they'd done a biopsy. I was admitted and receiving my first round of chemotherapy within three days and they were, I have to say, exceptionally good exceptionally good.

Shawn:

This all raises a massive, unsettling question If the US is supposedly the pinnacle of wealth and progress, why are so many of its citizens terrified of getting sick For millions? The realization is simple they can either spend their lives rationing medicine and avoiding doctors, or they can move abroad and access the basic human right to health care without the constant threat of bankruptcy. And when you frame it like that, it's less a radical life decision and more basic survival strategy. Let's talk about something equally soul-crushing the grind. Because, let's be honest, americans don't just work. We grind, we hustle. We proudly glorify exhaustion like it's a competitive sport.

Shawn:

The average American works about 2,080 hours per year. That's hundreds more than workers in Germany, france or the Netherlands. 55% of Americans don't use all their vacation days, even when they have them, and the US is the only industrialized nation that doesn't guarantee paid vacation or paid parental leave at the federal level. And it's not making us richer or happier. Studies show that Americans experience higher levels of stress, anxiety, burnout and depression than workers in countries that prioritize work-life balance. And, even worse, countries like Germany and the Netherlands, where people work fewer hours, actually have higher productivity per hour than the US. So we're working more, living less and somehow still falling behind.

Shawn:

And when it comes time for retirement, the finish line just keeps moving. The average American retirement age has crept up to 65 to 67 years old, compared to 60 or younger in much of Europe, and with Social Security's future looking shaky, many Americans are planning to work well into their 70s, if they're lucky enough to keep working at all. Meanwhile, in much of the world, they have a very different philosophy. This is Tim Leffel, award-winning travel writer and author of the books the World's Cheapest Destinations Travel.

Tim Leffel:

Writing 2.0, and A Better Life for Half the Price, explaining this phenomenon. So there's all these different reasons that people have for moving abroad and some of them, you know, it's just a quality of life issue. You know, once you get out of the US you kind of breathe this big sigh of relief because you get away from 24-hour news, you get away from the workaholic attitudes, you know, you get away from the stress and you're often healthier too. Because you're walking more, you're not, you know it. Because you're walking more, you're not, you know, it's not such a car culture. You're eating better because fruit and vegetables are not so expensive. It's easier to eat organic in a lot of places, especially Europe. I mean, that's kind of the norm instead of the exception.

Shawn:

In Sweden, the concept of lagom just enough permeates the culture. Overworking isn't a badge of honor, it's seen as inefficient. Workers typically get 25 to 30 paid vacation days per year, and in France, full-time employees get a minimum of five weeks of paid vacation annually, plus holidays. And thanks to the 2017 Right to Disconnect law, companies can't legally expect workers to answer emails outside of work hours. I mean, imagine that, not feeling pressured to check your email at 10pm or work on weekends. In Costa Rica, the national motto, pura Vida, is about prioritizing well-being, community and enjoying life, and they don't just say it, they live it. Costa Rica ranks among the happiest countries in the world, largely because of its laid-back lifestyle, strong social networks and focus on health and nature. Many expats say they moved to Costa Rica to escape stress, long work hours and financial pressures, and found themselves actually enjoying life for the first time. These are American expats, zanta and Dana, who have made the move to Costa Rica, explaining this Pura Vida lifestyle.

Xanthe and Dana:

Our culture is very go, go, go, go go. You know fast food. You go to the restaurant, everything. You really do have to slow it down. They don't live like that and I think they it would be kind of offensive to them like what? Like why they're, they're really embrace that Pura Vida culture. So, like you know, at a restaurant that you don't expect, like you're standing there, you know you might not have a host like run up to you and be like, oh, we'll get your thing. I mean it just might be a minute. You know, same thing with your drinks, with your food.

Xanthe and Dana:

Like you know there's no, the time here is different. Like everything goes with sunrise, sunset and it doesn't really change. We don't have any time change here. We don't have any time change here. And you're close enough to the equator. Like you know, sun comes up about five 30 and the sun sets about five 30. Like it's people really kind of work and play around that. Like it's you know, and it's it's one of those places like still at sunset people drive out every single day to the beach and or walk out to see the sunset come flying in cars.

Daniel Tostado:

I saw one last night just come flying in.

Xanthe and Dana:

That was great because it was like, look, they made the sunset. Yeah, it's different. And like, coming from like I love the beach, I love to surf, every day I'm out there. It kind of reminds me of like what California must have been like a long time ago. Like all the beaches in Costa Rica are public On Sundays, like a lot of the locals come from San Jose and they've got grills and music and fun and coolers yeah it's called the People's Beach and you don't pay for parking anywhere.

Xanthe and Dana:

Like you know, you can't even be close to a California beach without having to pay. You know parking and all that. So it's very, it's just very different.

Shawn:

Spain takes work-life balance to another level. The traditional siesta culture still exists in some parts of Spain, allowing workers to take a long midday break to eat, rest or spend time with family before returning to work. The standard work week is typically 35 to 40 hours, and long lunches or coffee breaks are considered normal. The cost of living is lower, meaning people don't have to work excessive hours just to cover basic needs. Spain isn't just about less work. It's about valuing life outside of work. This is Karen McCann again, who has written numerous books about her travels and divides her time between Spain and San Francisco, explaining this unique Spanish approach to time and community.

Karen McCann:

You know, you read that they have later lunch and later dinner and you kind of get your head around that. But the whole attitude towards time is different. The idea in Spain is if you bump into a friend on the street, you go and have a coffee. You always make time. You make time for your friends and family in a way that Americans really don't anymore. It's just built into the culture they seem. In Spain, they seem to have the idea that they have more time than they could possibly use. They are very generous with it and it's so refreshing. When I'm in the States, if I wanna have dinner with somebody, I have to make an appointment two weeks in advance, even with my sisters, whereas in Spain we often bump into somebody on the street my husband and I and they'll go hey, what are you doing tonight? And the next thing we know we're all going off and having dinner together. It's just a different attitude towards time.

Shawn:

For many Americans, hearing about these cultural norms is like hearing about unicorns a world where work doesn't consume your life, where taking off isn't seen as slacking, where weekends are actually for relaxing. It sounds almost suspiciously good, and it raises yet another uncomfortable question. If other countries have figured out that happiness, health and balance matter just as much as GDP, why are we still glorifying burnout like it's some kind of virtue? All right, so maybe it's time for a reality check Before you start packing your bags and practicing your French. Let's talk about the part that Instagram travel bloggers don't always tell you.

Shawn:

Moving abroad is not a magic escape hatch. Yes, it can be life-changing, yes, it can be wonderful, but it also comes with a unique set of challenges that no amount of wishful thinking can erase. So let's break down a few of them. Getting legal residency in another country is not like joining a rewards program. You're going to face probably quite a bit of paperwork, income requirements that aren't always super clear and changing rules that can leave you scrambling halfway through your application. For example, portugal's popular D7 visa, which used to be an easy option for retirees and remote workers, recently tightened income standards. Thailand's visa options for long-term stayers have fluctuated so much and so often that even immigration lawyers can lose track. And in Japan, unless you have a long-term employment contract or you're marrying a citizen, your chances of permanent residency are roughly the same as winning the Powerball. You'll need to budget time, patience and probably a little cash for legal help along the way.

Shawn:

There are also cultural adjustments. You might think you're prepared for life abroad. If you've watched a few YouTube videos. You've learned how to say where's the bathroom in Spanish. But trust me, culture shock is real. Even simple stuff gets complicated Paying utility bill, finding the right doctor, understanding when stores are open or why they randomly close on Wednesdays. This is Heather Mason, creator of the Two Summers blog, explaining her experience trying to set up a bank account in South Africa.

Heather Mason:

There's a lot of red tape around banking in South Africa, I think, because historically there has been a lot more corruption and fraud. Well, I say more, there's a lot of corruption and fraud in the banking system here. So it's actually very hard to get a bank account, and I think I lived here for three years before I was able to get my own bank, maybe even four. It took me a long time, which was very difficult. I mean, I spent a lot of time paying my rent and bills in cash because I literally couldn't get a bank account until because here you can't get a bank account until you have a proper visa, and it took me quite a few years to straighten that out. So and I you know you can't get if you have a spouse visa, for example, you can't open a bank account. You can only use your spouse's bank account.

Heather Mason:

So anyway, I finally got one and and I I am very careful to make sure you know cause, if your visa, if you, if your visa lapses, for example, you have a bank account, the bank will freeze your account. So you really have to stay on top of that and make sure your visa is up to date and that you've reported. You know all of your information to the bank at all times. And then cell phone yeah, all the things that you need in addition to that, like cell phone, contract, health insurance, all those things. They're also kind of hard to get if you don't have a bank account.

Shawn:

In Spain, stores still shut down in the afternoon. In Japan, trying to understand rigid social etiquette can feel insurmountable. In Germany, cash is king and credit cards aren't always accepted. And then there's the bureaucracy. If you think US government websites are bad, wait until you try to get a residency permit in a country where the forms are in four languages, none of them yours. These frustrations are part of the journey, but if you aren't prepared, they can quickly turn that idyllic expat dream into a daily grind of confusion and mild rage.

Shawn:

Here's something else that a lot of people don't realize until they're staring down April 15th, the first year after a move. The US taxes you, no matter where you live. The United States is one of only two countries in the world the other is Eritrea, good company that taxes its citizens on worldwide income. So even if you move to Portugal, thailand, costa Rica or anywhere, you still have to file a US tax return every year, report your foreign bank accounts if they total over $10,000, and potentially pay taxes depending on your income, credits and deductions. Here's David Lesperance, founder of Lesperance Associates, a group of international tax and immigration advisors, outlining some of the tax realities Americans need to consider when moving abroad.

David Lesperance:

A US citizen, even if they move to a jurisdiction which has no tax, will still owe US federal tax and still have US financial reporting on things like foreign bank account reports, fbars and mutual funds, pfics and a variety of different things, if they're going to be moving to a jurisdiction which has a tax regime. Many countries do, which you can, either because they have a specific regime. For example, we'll look at Europe. The UK is just getting rid of a regime they had called the remittance or non-dom system, but Ireland, cyprus and Malta still have that system. Other countries such as Italy, greece and Switzerland have said we're going to have a lump sum. So if you move to Italy, it's 200,000 a year euros 200,000 euros. Whether you make a dollar or 200 million, it's 200,000 a year euros 200,000 euros. Whether you make a dollar or 200 million, it's 200,000. One of the other advantages of a lump sum jurisdiction is the tax becomes a line item. You also don't have to pay your accountant for complex returns. You also don't have to look at this very complex tax return as you sign it and think to yourself gee, I hope my accountant got it right.

David Lesperance:

Other countries such as, for example, canada they have some pre-immigration tax planning. They may also have different things, like Canada, for example, doesn't have an estate tax or a gift tax. So it's looking at all the different regimes and how they interact. If the person is giving up their US citizenship there is some, depending on what their net worth is and generally unless they have a specific exemption to this regime the clients who would consider economically an expatriation they will trigger an exit tax, a taxation on unrealized capital gain. There is an exemption it's a little over $900,000 right now, but they pay the top federal rate on everything above that and there's also an inheritance tax. So there's some complex planning that we can do beforehand. But they've just jumped out of the US tax pot. They want to make sure they don't jump into another tax buyer so they may move, for example, to one of the various jurisdictions what are normally thought of as high tax countries, but on a lower controlled tax basis because they have these special regimes.

Shawn:

Now there are treaties and exclusions that can help you avoid double taxation, like the Foreign Earned Income Exclusion, feie, but the paperwork is complex enough that you might need a specialized international tax advisor. Good news, though We'll dig into all the tax realities in much more detail in an upcoming episode, but for now, just know moving abroad does not mean breaking up with the IRS. But for now, just know moving abroad does not mean breaking up with the IRS. Also, if your plan is to work from anywhere as a digital nomad, you'll need to double-check the rules, because not every country smiles upon laptop warriors working under tourist visas. Spain and Portugal are two of many countries that offer special digital nomad visas, but they come with income minimums and application hurdles, each different for each country. Thailand doesn't allow remote work on a tourist visa at all, and people have been deported for violating it. Japan has very limited pathways for freelancers and remote workers. The bottom line here is if you plan to work abroad, make sure you understand what's legal and what could get you a one-way ticket home. So, after all that, should you stay or should you go? The answer is, like most important things in life, complicated.

Shawn:

Moving abroad can be life-changing, financially liberating, spiritually refreshing and, yes, sometimes even wildly fun. But it also comes with paperwork, language barriers, culture shock, a steep learning curve. It's not a fairy tale. It's not a permanent vacation. It's real life, just somewhere else, and like any real life, it comes with trade-offs. You might save money, live healthier and feel freer abroad, but you'll also need to adapt, learn and be willing to start over in ways, big and small.

Shawn:

If you're flexible, curious and ready to embrace change, leaving America could be the best decision you ever make. And if you're now thinking okay and ready to embrace change, leaving America could be the best decision you ever make. And if you're now thinking okay, maybe this is for me, but where would I even go? That's exactly where we're headed in our next episode, when we'll be talking about some of the easiest and most popular escapes for Americans. We're going to cover the most popular visa programs, how much you realistically need to live comfortably and some of the hidden challenges to making the move, challenges that just a little preparation can mitigate. 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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