How to Move Abroad Without Losing Your Money, Time or Hair

Most people dream of retiring abroad, but just one wrong move can destroy that dream.

These are the 10 most common mistakes we see that derail that dream. If you know them now, you can avoid them entirely.

I’m James Nuveen, an American expat and investor who helps US citizens retire earlier and live freer lives overseas. After a decade abroad, I’ve seen it all – from botched visas to surprise taxes to healthcare disasters. 

So before you plan your move, watch at least until #7 (which I think is most important). This could save you your peace of mind, thousands of dollars, and months of your precious time.

Mistake 1: Assuming You Don’t Need to Learn the Local Language

Let’s start with mistake #1 which sounds harmless but can actually ruin your entire experience abroad: Assuming you don’t need to learn the local language.

Now, I’m not saying you need to be fluent in a foreign language tomorrow.

But I’ve watched dozens of expats move to a new country thinking they’d “get by” with English or a translation app and end up feeling isolated and unsafe because they can’t communicate with the people around them.

One couple we worked with moved to a mountain town in Mexico. Obviously, no local saloon or spa for them to pass time by with fellow expats. Two weeks in, they couldn’t communicate with their landlord about a major issue in their condo. And as anyone would, they started second-guessing their decision.

Language isn’t about grammar. It’s about the freedom to get help, to make friends, to feel at home in a foreign land.

I lived in 10 Latin American countries in my first two years abroad and learned conversational Spanish in just 6 months. When you’re immersed in it, Spanish, French, Italian – the Romance languages are far easier than you may think to learn. Thai, Japanese, and Turkish are another story.

But start simple: 10-15 everyday phrases. Locals will respect you more. You’ll feel more comfortable. And your lifestyle will thank you for it.

Mistake 2: Overlooking Political Stability and Long-Term Safety

Mistake #2 is harder to spot and way more dangerous: Do not move somewhere without understanding its political or long-term stability.

Most people pick a country because of weather, lifestyle, or cost of living, not realizing the country is on shaky ground or worse, a total shitshow.

That coastal town in Costa Rica may look appetizing. Buy a condo, set up utilities, the works. But after two years when that honeymoon phase ends and your rose-colored glasses come off, local laws might change, property ownership gets murky, crime starts climbing. Then, you have to sell fast and lose money in the process. 

What looks like paradise now might not stay that way. Just look at the United States! This is the on-the-ground reality most travel vloggers don’t cover.

We help our clients understand what they’re getting into before they make any investments overseas. This is critical.

Mistake 3: Buying or Renting Property without Knowing the Rules

This one trips up even the smartest retirees: Do not buy or rent property overseas without fully understanding the local laws.

Every country plays by a different rulebook. And sometimes that rulebook changes abruptly without announcement. 

Spain is proposing a 100% tax on foreign-owned property in the country. Portuguese homeowners deal often with squatters. US expats can’t buy beachfront property in Mexico without a fideicomiso or Mexican corporation. Other countries have strange inheritance laws where your property gets tangled in local courts if you pass away. 

I’ve seen people lose homes because of paperwork they didn’t understand. You don’t have the same rights as in the United States. 

Buying? You better know what “fiduciary title” means in that country. Renting? Make sure you know your tenant rights before you sign anything.

Tip: Always have a bilingual attorney – one who works for you, not the real estate agent.

And rarely, if ever, wire an international deposit before you’ve set foot in the place. No matter how good it looks on Facebook.

Mistake 4: Skipping the Legal Steps to Establish Residency and Access Services

Mistake #4 separates the tourists from the expats. Skipping the residency process or treating it like an afterthought is one of the fastest ways to get deported, pay a massive fine at customs, or lose access to healthcare.

Look, you might think, “I’ll go on a tourist visa first and figure it out later.” But later often turns into an overstayed visa and a red flag on your immigration record.

We’ve had clients stuck in this bureaucratic limbo – can’t open a bank account, can’t rent long-term, can’t even get a SIM card – because they never got their paperwork and calendar in order.

The residency process doesn’t have to be hard, but it does have to be done right. And every country has its quirks: Always plan ahead and start the immigration process before you think you should.

Mistake 5: Thinking You Can’t Access Social Security or Investment Income Abroad

Mistake #5 causes unnecessary fear and stops people from ever taking the first step. No, you do not lose access to your Social Security if you move abroad.

But there are rules. And if you don’t know them, you can screw it up.

You can collect your benefits in over 180 countries but not all. Some countries, like Cuba or North Korea, are restricted. Let’s be clear though: The Freedom Files has never and will likely never help you move to Pyongyang. 

Our advice is to follow the correct steps: Sure, you can continue getting deposits in the US and use your banking cards abroad, sometimes with extra fees. But if you set up a local bank account abroad, you need to report that to the US Embassy or Social Security Administration to avoid frozen payments.

Same goes for retirement accounts. IRAs, 401Ks, brokerage accounts – You can still access them abroad.

But some investment platforms will freeze or restrict your access if they see a non-US address on file.

The good news though? You don’t need to close your US accounts. But you do need to structure your financial setup properly. We can help with this and much more.

Mistake 6: Ignoring Local Healthcare and Insurance Requirements

Healthcare abroad can be vastly better and cheaper than in the US. But assuming you can just walk into any hospital in any country and get treated like a local? That’s mistake #6.

Most countries offer high-quality care at a fraction of US prices but only if you know how their system works. Some countries have public systems you can buy into once you’re a legal resident, not a tourist. Many jurisdictions won’t even let you apply for a visa without proof of coverage in their territory.

Story time: A guy and his wife from DC recently applied for the Italian Elective Residency Visa. Everything was ready. But because he didn’t have the correct proof of insurance in Italy, they denied him at the final step. It delayed his move by four months, and they came to us for help.

The necessary coverage depends entirely on the country and the visa for which you’re applying. In Colombia where we help many US citizens move, Investor Visa holders must buy local insurance while Retirement Visa applicants must have a global insurance plan. The rules are funky, but the rules are rules.

Just don’t ignore this. Don’t delay it. And don’t assume Medicare will follow you overseas because it won’t.

Mistake 7: Underestimating the True Cost of Living Abroad

Perhaps the most important on this list, mistake #7 hits people after they’ve landed. YouTube videos had told them that “Ahh! This place is so cheap!” and six months later, their bank account is bleeding.

Yes, many countries have dramatically lower costs than the US, but that depends on where you live, how you live, and whether you’re paying “local” or “gringo” prices.

Look at the cost of living comparison between Brazil and the United States. These prices compare what local salary earners pay for goods and services. But the average monthly wage in Brazil is $600 while the average wage in the United States is a few thousand bucks. This contrast is even more stark when you compare the Brazilian countryside with an American city.

But you don’t move to Brazil to live like an average local – neither of those attributes in fact. You move to Brazil to live healthier, happier, wealthier, and better than you do at home. 

You can absolutely live well on $1,500 a month in parts of Ecuador, Vietnam, or rural Portugal, a comment we hear often in our Freedom Consults. But try that same lifestyle in Lisbon, Buenos Aires, or Bangkok? You’ll spend twice as much.

The truth is: You can live better overseas for less, yes. But some destinations may require an adjustment of your expectations. 

Before you move, build a realistic monthly budget for your lifestyle, not just what a YouTube video or ChatGPT says is “average.” You’re not average and you shouldn’t live out your golden years as if you are. 

Mistake 8: Misunderstanding How Your Retirement Income Will Be Taxed

If there’s one mistake that really costs you, it’s mistake #8: Not understanding how your income will be taxed both by the US (if you’re an American resident or citizen) and by your new country.

Just because you move abroad doesn’t mean you stop owing US taxes. If you’re a US green card holder or citizen, you’re taxed on worldwide income – no matter where you live – until you give up that status.

But here’s where it gets tricky: Some countries don’t tax your foreign income. Others do. Some countries offer amazing tax breaks for retirees. Others… ehh, not so much. Every country that you consider moving to has different rules and regulations.

We just helped a retired US navy pilot move to France. He had zero idea that French law excludes from taxes US social security and retirement income. Happy little surprise that allowed him to increase his budget by thousands of dollars each month.

We’ve covered on this channel the special 7% tax regimes in Italy and Greece as well.

The point is: Tax strategy is location-specific.

Mistake 9: Forgetting Residency Maintenance Requirements

Okay, you and your wife got the visa. You guys moved abroad. You’re loving your new routine, maybe even slow traveling between a few countries. But then… boom. A year later, your residency expires and no one told you about it.

That’s mistake #9: Forgetting to maintain your residency overseas.

Most countries require you to hold your investment (if applicable) or spend a minimum number of days in-country each year to keep your visa or residency active. Miss that threshold – even by a dollar or a day – and you may be forced to reapply from scratch, lose your status, and extend your timeline to citizenship.

One of our clients had a long-term visa in Panama. Spent too much time back in the States helping with a family issue and lost it. When he tried to return, he had to start the entire process over. Very frustrating. 

Some countries, like Colombia, require just a single day every 6 months. Others, like Spain, want you there for more than half the year to claim you as a tax resident. Some are flexible, others not.

Before you apply for a particular visa (which we’ll talk about next), make sure you know how much time you need to spend in-country, how to maintain your investment if you made one, and how to keep the validity on your visa.

Mistake 10: Choosing the Wrong Visa or Residency Path

Last but not least, mistake #10 causes more stress, more delays, and more legal chaos than any other: That is, Choosing the wrong visa or residency path for your circumstances and goals.

Not all visas are created equal. Some are meant for tourists and limit your rights. Some are powerful and lead to permanent residency and citizenship. Some just require proof of income (we call these Independent Means Visas) and others require a business investment, hiring, property purchase, or donation.

As you can see, there’s a wide range of visas designed for a wide range of expats. Our job is to help you find the right one for your situation and goals in the country.

We’ve worked with retirees who should’ve applied for a Retirement Visa at their American consulate, yet instead entered the country on just a tourist visa and were trapped. We’ve worked with investors who’ve moved hundreds of thousands of dollars from the US into countries with residency by investment programs but didn’t know how to legalize their funds, exchange the currency, and apply for the visa all at once. And some of our clients hired the wrong lawyer or trusted the wrong YouTuber and went down a path that cost them time, energy, and a hell of a lot of cash.

The good news? You probably have more options than you think, especially if you haven’t yet chosen a destination. Retirement visas, digital nomad visas, golden visas, residency by investment, citizenship by investment, tax incentive programs. We cover them here on the Freedom Files, on the website, and in our 1-on-1 Freedom Consults. 

Moral of the story: Don’t make these ten mistakes when moving abroad. Do your research. It saved me when I first left the US and now I’m paying it forward. Continue down the rabbit hole and watch this breakdown of the 7 best countries to retire in 2025, including visa types, cost of living data, and tax benefits. I’ll link it right here.