I Left My Home Country 6 Years Ago. If I Would Leave In 2026, Here's What I'd Do Differently.
6 years, 3 relocations, and every mistake in between
In November 2020, I handed my landlord the keys to a flat I’d lived in for 5 years, sold most of what I owned for about 40 cents on the euro, and flew to Cyprus with one suitcase and one backpack.
I told myself I’d somehow figure it out.
Six years later, I’ve lived in three countries (Cyprus, UAE, Thailand).
I’ve opened and closed bank accounts on three continents, overpaid $8,000+ in currency transfers because I didn't time it right. I stored furniture for five months that I ended up selling at a loss anyway.
Some of it was worse than that.
A broker closed my accounts and forced me to sell. A business arrangement turned out to be a scam and cost me close to six figures.
Some of it was better than I imagined.
I started successful businesses, built up real savings and investments, opened 3 companies, obtained 5 residencies, bought property, booked 126 flights, and visited over 40 countries.
I screamed, cried, laughed and felt all the emotions out there. But there is one thing I never felt:
Regret.
Because the truth is, for better or worse, all those experiences shaped who I am today.
However, some of the things I did could have been done better.
If I left Germany today, in April 2026, I would do it differently.
I’d do it in a specific order, because the order matters more than any single decision.
This article is that order.
Six phases, from first questions to first 90 days abroad.
Each one builds on the last.
Here’s what we’ll cover:
How to figure out what you actually need before you start googling countries
How to clean up your financial, legal, and personal life before you leave
How to research, test, and commit to a destination without wasting time or money
Phase one starts with you.
Know Yourself Before You Pick The Country
I landed in Larnaca in December 2020 with a list of reasons Cyprus was “the right country.”
Low taxes, EU country (needed for my company setup), English widely spoken, warm weather.
I pulled those reasons from a listicle. I didn’t pull them from myself.
By June 2021, I knew I’d picked wrong.
The summers hit 40°C and Larnaca became a ghost town. The social scene was small enough already (and I thrive in big cities).
Cyprus checked every box I had on paper.
But I hadn’t figured out what my actual boxes were.
I’ve watched at least a dozen people who come to me sooner or later making the same mistake.
They look for “best countries to retire/start a business in 2026,” read five articles, bookmark two of them and start comparing visa costs.
The whole process is backward.
You need to start with yourself.
Not the “vacation version” of you.
The “Tuesday-morning-in-January I need this specific kind of coffee this morning” version.
That means answering questions you probably haven’t thought about yet:
What pace of life do you actually want, and have you tested that assumption? (A lot of people say “slow and relaxed” until they’ve spent three weeks in a beach town with nothing to do.)
How important is it that the people around you speak English, not just at the hotel front desk, but at the pharmacy, the hospital, and the government office where you’re filing paperwork?
Are you looking for an expat community of people like you, or are you comfortable being one of very few foreigners in your area?
How much patience do you have for bureaucracy? Some countries process a residency visa in 30 days. Others take a year and lose your paperwork twice.
I built the “Global Fit Quiz” inside the Expat Country Decision Kit for exactly this reason.
15 questions that force you to be honest about money, healthcare, climate, social needs, proximity to family, and daily logistics.
And to make it easier for you, you can download them here for free.
The answers won’t point you to a country yet (that part comes later).
What they’ll give you is clarity on what you’re actually looking for. Not something vague like “somewhere warm and cheap” but “I want to walk to a cafe every morning, I want a community of people my age, and I need to be able to fly home in under 8 hours.”
That level of specificity changes every conversation you have from this point forward.
Takeaway: Start with YOU, not with a country. Know what you want before you look at what’s possible.
Know Your Situation Before You Make Plans
Now you know what you want. This section is about what you can actually do.
The distance between those two is where most relocations either come together or fall apart.
I wanted to go to Singapore. I had quit my job in Germany, lined up a position, and had a visa approved. Then COVID turned my world upside down. When I had to pivot, I sat down and looked at what I was actually working with: $11,000 in savings, $90,000 in student debt, no clients, no freelancing experience, and a family in Europe that was scared about a pandemic nobody understood yet.
Singapore on $11,000 would have lasted maybe two months. But the money was only one part of it. I’d lived in Australia and the UK before, and both times taught me something: I needed to be close to family, at least for this chapter of my life. During COVID, that meant Europe. So two pieces of my situation (savings and family) had narrowed my options from “anywhere in the world” to “somewhere cheap in the EU.”
Each honest answer eliminates options you thought you had.
I ended up in Cyprus. The cost of living was low, especially during COVID. Rent was affordable. I knew I could survive there longer than anywhere else on my list. What I didn’t know was whether I could find work before the money ran out. I got lucky with a consulting client three weeks in. But luck is a terrible strategy, and I’d never recommend it.
The audit you need to do before picking a country covers more ground than you’d think. Finances are the obvious starting point, but it goes deeper than “how much do I have saved.” What does your income look like when you stop working, or when you work from a different time zone? If you’re on Social Security and a pension, how does that money actually reach you in another country? What about your property: are you selling, renting it out, or letting it sit?
Then there’s your health. Ongoing conditions, regular medications, whether your spouse needs specialist care, your comfort level with a hospital where the doctors don’t speak English. These questions matter more than which country has the best weather.
And then the pieces that don’t fit neatly into a spreadsheet:
Who is coming with you?
Is your spouse actually on board, or just going along with it?
Do you have kids or grandkids whose ages and locations will shape how far you can go?
Aging parents? Pets? (Yes, pets. Moving a dog internationally is its own project.)
What ties make leaving hard, and which of those ties are you willing to stretch?
I’m compressing a lot here. This audit is something I do with clients, and it takes a full call and homework. There are layers to each of these that take time to think through honestly. But you can start on your own this weekend. Sit down with a blank page and write out your income, your savings, your debts, your health situation, who depends on you, and what’s keeping you where you are.
Be specific: Dollar amounts. Names. Dates.
The goal is to see your situation clearly enough that when you start researching countries in the next section, you’re comparing them against reality (instead of a fantasy).
Takeaway: Desires tell you what you want. Analyzing the status quo tells you what’s actually possible. The gap between them is where the real planning starts.
Know Your Options Before You Commit
Now you know what you want, and you know what you’re working with. This is the time to start looking at countries, and for the first time, you’ll be looking with filters instead of fantasies.
By the way, this is where most people start their relocation process. But it should be step three.
When I was choosing between Malta and Cyprus in late 2020, I didn’t have a framework. I picked the “bigger island”. That was my entire decision-making process. It worked out, but only because my situation was simple: I was young, single, had no dependents, and just needed somewhere cheap in the EU. Your situation is probably more complex than mine was.
The research phase has two parts: strategy first, then countries.
Strategy means deciding what kind of international life you’re building. Are you moving full-time to one place? Splitting time between two countries? Keeping a US base and spending winters abroad? Each of these has completely different implications for taxes, visas, healthcare, and cost. A full-time move to Portugal is a different project than spending four months a year there on a tourist visa while keeping your house in Florida.
You need to decide which structure fits your situation before you start comparing countries, because the structure determines which visa categories, tax treaties, and residency paths are even relevant to you.
Once you have a strategy, the country comparison gets much tighter. Instead of browsing “best countries for retirees” listicles, you’re asking specific questions. Which countries offer a retirement visa that fits my income level? Which ones have tax treaties with the US that work for my situation? Where can I access the healthcare I need? Which ones let me bring my dog without a six-month quarantine?
The part that you need to accept: Every country is a trade-off.
Portugal has good healthcare and an easy residency path, but the tax situation has gotten more complicated since they ended NHR in 2024. Mexico has proximity to the US and low cost of living, but healthcare outside the major cities has gaps. Thailand is cheap and the food is incredible, but you’re 20 hours from the East Coast.
No country gives you everything.
The question is which trade-offs you can live with, and you can only answer that because you did the work in Sections 1 and 2.
I’d also say this: don’t trust a single source. I’ve read country guides that were three years out of date, blog posts written by people who visited for two weeks, and YouTube videos from creators who make money by selling you on a destination. What was true 18 months ago might not be true now.
By the end of this phase, you should have a shortlist of less countries that you were considering before, and a clear strategy for how you’ll structure your time, and a rough sense of the visa path, cost, and timeline for each.
Write it down this way:
I’m looking at X and Y, because of Z.
My strategy is [full-time / split-time / seasonal].
The visa I’d apply for is [specific visa name].
The estimated timeline is [months].
That’s your working plan. The next step is to go test it.
Takeaway: No country is perfect. Simple as that.
Test Before You Commit
I cannot stress this enough: do not sign a lease or apply for a visa until you’ve spent real time in your top choice. Not as a tourist, but as someone testing what daily life actually feels like.
I read it over and over again: people who skipped a scouting trip and say everything worked out fine. And maybe it did. But why would you skip it? You wouldn’t buy an expensive car without a test drive. Relocating is not trying out a new restaurant where a miss costs you $100 and a wasted evening.
It changes your life.
I didn’t do many things I now recommend when I relocated for the first time. But even I scouted Cyprus a month before my move.
So, what is a scouting trip? A scouting trip is not a vacation. It’s a research project with a deadline. You’re checking apartments, visiting hospitals, opening a local SIM card, figuring out how the grocery stores work, and eating at the places you’d actually eat at on a Tuesday.
I recommend a minimum of three weeks. The first two weeks, you’re still in vacation mode. Everything is new and exciting. Around week three, the novelty fades and you start noticing the things that will matter in month six: the noise at night in your preferred neighbourhood or the commute to the nearest hospital.
I wrote a full scouting trip playbook with a 21-point checklist covering logistics, housing, healthcare, finances, legal, daily life, and social environment. It walks you through exactly what to do, what to check, and what to document during your trip.
When you come back, you should be able to answer one question clearly:
“Can I see myself living here for a year?”
If the answer is yes, you move to the next phase. If it’s “maybe,” go back for a second trip, ideally in a different season. If it’s no, that’s valuable too, since you just saved yourself a very expensive mistake.
Takeaway: A three-week scouting trip cis cheaper than a wrong move.
Commit And Set Up Before You Go
Now comes the phase I skipped entirely 6 years ago: the preparation between deciding and leaving.
When I left Germany, I sold most of what I owned in about two weeks, didn’t organize my documents, and boarded a flight with almost nothing in order. I had to get papers shipped from Germany during COVID. Slow, expensive, and completely avoidable. I didn’t cancel subscriptions I wasn’t using. I didn’t set up a power of attorney. I didn’t think about what would happen if someone needed to act on my behalf back home.
This phase is boring and it takes longer than you think.
Here’s what goes into it.
Get your documents in order
Passport (with at least 12 months of validity), birth certificate, marriage certificate if applicable, medical records, insurance policies, recent tax returns. Anything that might need an apostille, get it apostilled now. The process takes weeks in some states, and you cannot rush it. Make digital copies of everything and store them somewhere you can access from anywhere.
Sort out your money infrastructure
This is where banking comes in. Set up a Wise or Revolut account before you leave. Research whether you can open a bank account in your destination remotely, and what documents you’ll need if you have to do it in person. Keep your US bank account open. I use a three-account structure: a US home base, a fintech bridge for transfers, and a local account in the country I’m living in. Plus I use more sophisticated advisors for my investments. Have a look at the article below, or download the US Expat Money Guide for insights on different strategies for your investments.
Health and insurance
You need international health insurance or a local plan in your destination. Research this before you leave, not after you arrive with a toothache and no coverage. If you take regular medications, figure out availability and bring enough supply to cover your first months.
Handle the loose ends
Cancel subscriptions and services you won’t use. Forward your mail or set up a virtual mailbox. If you own property, decide whether you’re selling, renting, or holding. If renting, get a property manager in place before you go. Set up power of attorney for someone you trust back home. Get a will that works across jurisdictions, because most don’t.
Visa application
By now you know which visa you’re applying for. Some you can apply for from the US. Some require you to be in-country. Some have processing times of 60 to 90 days. Some require proof of funds sitting in a specific bank account for a specific period. Start the application as early as the rules allow. The number one mistake I see with clients is underestimating how long visa processing takes.
Most of this is logistics and none of it is exciting. But every item on this list is something that becomes ten times harder to deal with once you’re in a new country, in a different time zone, with limited access to your old systems.
Takeaway: The best time to get residency is when you don’t need it. Prepare while your life is still organized.
Build Your Life In The First 90 Days
The preparation is done.
Now comes the part nobody can fully plan for.
The first 90 days abroad will be the hardest stretch of the entire process. Not because anything goes wrong necessarily, but because everything is new at once. New grocery stores, new pharmacies, new SIM card, new landlord, new bank, new language for the guy fixing your internet. It’s exhausting in a way that a two-week scouting trip doesn’t prepare you for.
A few things I learned across four countries.
Get your administrative setup done in the first two weeks.
Residency registration, local bank account, SIM card, utility accounts. Front-load the bureaucracy while your energy is high. After week three, you won’t want to sit in another government office.
Then build a routine. I don’t mean a productivity schedule. I mean something that makes a Tuesday feel like a Tuesday. A coffee shop you go to. A walk you take. A gym or a pool. The people who struggle most abroad are the ones who never build a daily structure and spend their first six months feeling like they’re on an extended layover.
Meet people early. Join expat groups before you arrive. Show up to things even when you don’t feel like it. My first real friend in Cyprus came from a Facebook cycling group. It felt random at the time. Looking back, it was the single thing that made Cyprus feel like home instead of a temporary stop.
I’ll write a full first-90-days playbook in a future article. For now, know this: the move itself is the “easy” part.
Building a life takes longer. Give yourself permission for it to be messy and slow.
Takeaway: The life you build in the new place takes work. Start on day one.
Conclusion
That’s it.
Six phases.
Know yourself.
Know your situation.
Know your options.
Test it.
Commit and set up.
Build your life.
In that order.
The sequence matters more than any single decision. Skipping the self-audit is how people end up in countries that look good on paper and feel wrong by month four.
Also never forget that every country is a trade-off. The goal is finding the trade-offs you can live with, not finding a place with no downsides.
One thing you can do this weekend:
Sit down with a blank page and write out what you want (Section 1) and what you’re working with (Section 2). Be honest and put numbers on it. That single exercise will tell you more about your move than six months of browsing Reddit threads.
Where are you in the sequence right now? Still figuring out what you want? Deep in country research? Already done a scouting trip?
Reply and tell me. I read every response.
That’s it for this week.
Thanks for reading, and as always, appreciate having you here.
— Ben
PS
If you are an American 50+ and want to move abroad within the next 0-5 years, and don’t want to navigate healthcare, banking, visas, taxes and country selection by yourself, reply to this mail with “RETIRE”.
You’ll get an invite to the “Retire Abroad Priority List” with some of my best tactics for retiring abroad.
And if you would like to have someone in your corner to build your custom roadmap with options you might have never heard of, you can book a call with me here.