My identity was stolen in October of 2023. It was a nightmare.

I was in Belize, and my bank accounts and everything that identified me were based in Canada. I had been abroad for 18 months and was dealing with the growing pains that come along with establishing oneself in a new country when the crisis hit.

What followed was one of the more eye-opening experiences of my life: A clarifying yet monumental undertaking to reclaim my monetary freedom that completely changed how I think and act in the world.

It’s an unsexy side of “moving abroad” and something that nobody puts in their highlight reel:

How to manage your life after a personal financial crisis.

When the fraud hit full force, the financial infrastructure I’d spent years building without much thought came crashing down. With valuable accounts frozen, I was forced to rejig what I previously thought was a solid financial setup.

I’m not writing this to scare you. Not every expat will have their identity stolen in their home country while they live elsewhere. But I want to share that experience because it forced me to rebuild, and in doing so, I built something much better:

A financial and communication setup that actually works when I’m not where my primary bank thinks I am.

It’s a system that isn’t just specific to me; anyone can create something similar. By sharing it, I hope to save you the trouble of figuring it out for yourself, undoubtedly the hard way.

The “Standard” Setup That’s Meant for People Who Never Leave

Note: I’m Canadian, so I’m going to frame everything in that lens. But feel free to substitute any institution’s name for one you’re familiar with. While the names differ, the systems are the same.

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Most people who move abroad inherit a financial and communication setup designed for residents. Big 6 bank, major telecom carrier, and maybe a PayPal account. It works fine when you’re home, but the moment you leave for good, it starts to work against you.

The costs are subtle at first. A roaming charge here, a currency conversion there. Then you realize you’ve been paying your phone provider over a grand a year just to turn your phone on abroad, caused by cumulative flat fees that kick in the moment your SIM connects overseas. Roger’s “Roam Like Home” is fine for vacation, but it becomes a serious financial drain long-term. Sure, you can try to batch all tasks that require two-factor authentication into a single session, so you only take one hit—as I used to do—but over time, that ceases to be a workaround. It becomes a significant tax on your own money.

Then there is the issue of opening a new account with one of the Big 6 from another country. They often want you in person, especially when you have a fraud alert on your credit report1, and it’s non-negotiable; a hard requirement. When I needed to rebuild my banking after the identity theft, the big institutions were simply not available to me. I was in Belize. They wanted me to visit a branch in person.

The alternatives, thankfully, are much better.

What Breaks First (A Short Inventory)

When I discovered the fraud, it nearly took everything at once. Accounts locked and a fraud alert on my credit file, freezing any further action. This hard stop on my finances revealed a fragility that was baked in from the start. I was forced to take a risk and leave my backup account (with another bank) open, so I had somewhere to move my funds.

So, there I am, sitting in Central America, trying to untangle it all over the phone, on a Rogers plan that charged me every time I turned my SIM on from abroad.

It was a lot of things at once. But mostly, it was clarifying. My setup was deeply flawed, and I needed something more robust.

More is Less: Why Redundancy Matters

Having more than one account was my only saving grace when my primary account was locked up due to fraud. But even that “safety net” proved fragile. A few weeks after the identity theft, while I had only one functioning account, I put my card into an unfamiliar ATM in Belize. The machine ate it.

True story.

I felt screwed: No backup digital card to make payments, and only a small amount of cash on hand. I was in a foreign country with a wife, two dogs, and two young children, left to ration cash so we could put food on the table until I could get the card back, which took a week: Five days of bureaucratic back-and-forth plus a weekend. It felt like a month. It was a reckoning. I was forced to face the fragility of my family’s financial setup, which had previously felt adequate.

Now I don’t settle for adequacy; I've set up redundancy.

Being reduced to zero access to funds in a foreign country makes you realize that redundancy isn’t a luxury; it’s critical infrastructure. Moving forward, I promised myself I would never operate with fewer than three independent accounts. You need a backup of the backup to handle worst-case scenarios in which both your primary and secondary accounts are compromised or physically lost.

I now have several layers of redundancy. Numerous points of financial access via physical cards linked to bank accounts and digital accounts with tap-to-pay, all interconnected, so I can move money between them quickly if one is compromised or inaccessible. All are protected with 2-factor authentication, so another ‘Freddy Fraudster’ can’t step inside my financial world and muck about. I also now keep funds distributed, so no single account holds everything. If one is frozen, the others still work, and lockups or losses aren’t catastrophic.

The beauty of all this is that it isn’t a complicated system. Does it take some time to set up? Yes, but it means having the financial equivalent of keeping spare keys somewhere other than in your own pocket.

And the goal isn’t to be a doomer or pepper, but simply to be ready for the unexpected and to avoid a financial disaster in a foreign land. The aim is to make any given problem smaller, changing a potential crisis into a manageable inconvenience.

The Stack I Built After The Crisis

I want to be specific here because vague advice about “diversifying your finances” is not useful. Here’s what’s actually useful and why.

Online-Only Banking

My banking is now online-only, mainly because that was the only option I had; I could actually apply from abroad with a VPN, a Canadian address, and a passport. Getting approved under an active fraud alert and police investigation while in another country was its own bureaucratic adventure, but it was possible, which is more than I could say for the Big 6. And honestly, after how badly CIBC handled my fraud case, even as a lifelong customer, I would never go back. Not to mention, opening an account with any of the Big Six comes with monthly fees.

I won’t say which bank became my new primary Canadian account because I’m still a bit paranoid about identity theft (even with the fraud alert purposely left on my account), but it costs me nothing to have and use. For fellow Canadians abroad, options like this include Tangerine Bank, EQ Bank, Simplii Financial, Neo Financial, and KOHO. The only caveat is that not all online financial institutions allow wire transfers, which makes real estate purchases impossible without an option that does.

Another benefit of online-only banking is knowing I will never get called into a branch for anything. Online banks don’t have physical locations, so all contact is made digitally. I can set aside any worry about being in a situation where I have to physically show up somewhere to regain access to funds, which would be a massive expense, just to keep an account open. I have also found that my primary bank account is more secure than the one I had with CIBC because it’s online-only, and I feel confident that my new bank will never compromise my identity the way CIBC did, thanks to the security features it has in place.

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Unfortunately, I don't have any advice for American readers, as the gazillion banks in your country make sorting through all the noise overwhelming and not a task I care to take on for this post.

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Local Bank Account

I don't have one of these yet, but I plan to open an account with a Belizean bank once my residency application is approved. This will allow me to deposit and hold Belizean currency and use a local debit card, providing an additional layer of monetary access and security.

Borderless Business Tools

Wise

This is the account I wish I’d had from day one. You get both a physical2 & digital debit card, multi-currency accounts, and the ability to send and receive money internationally at real exchange rates. I’d been using PayPal and Stripe for payments as a self-employed person working remotely, and painfully swallowing their user fees on a regular basis. Then I switched to Wise for receiving client payments, and reclaimed roughly 3% of my income that had been quietly disappearing with every client payment. For anyone running a location-independent business, that alone is worth the switch. And Wise allows international wire transfers for those planning big purchases in their host country, such as a vehicle or property.

Other fintech options in this space include Airwallex, which is fantastic for managing business expenses across multiple entities, and Payoneer, which remains a staple for freelancers receiving funds from global marketplaces and offers custom invoicing features.

The Investing & Management Hybrid

Wealthsimple

A solid backup account with a Visa debit card that earns interest on cash holdings and integrates cleanly with investing accounts if that’s relevant to you. They even have a digital card you can use to pay bills and deposit cheques. The platform also makes connecting to other financial institutions and moving money between accounts simple, which fits nicely into your financial redundancy layer.

Revolut

This is the ultimate hybrid of self-directed investing and international money management. It lets you hold multiple currencies, trade stocks, and even buy crypto all in one app. It’s a notable platform for those who need their money to be as mobile as they are.

Crypto

Shakepay

There are endless platforms out there for buying and holding this asset class, like Bitget, Coinbase, TrustWallet, Kraken, and BitMart, but this post is really about financial mobility and liquidity, which is why I like the Shakepay platform. For Canadians, this is a great option that blends everyday spending with crypto asset accumulation. It allows for easy money transfers between Canadian banks and other platform users, while providing access to a digital bank card, and the ability to buy and sell Bitcoin and Ethereum cryptocurrencies. You can also earn cash back, enable round-up on purchases, and earn interest on daily balances, all in Bitcoin. The digital card with a mobile phone tap-to-pay feature adds another redundancy if a bank machine eats your physical card ;).

Cash is King

Physical currencies—USD, Belizean dollars, and Mexican pesos for me— are still essential in our digital world. Not everywhere here is equipped to handle digital payments, and there are many places in Belize where plastic or RFID isn’t the primary option. So, if your digital setup goes sideways, cash is a non-negotiable backup and everyday necessity. No matter where you reside in the world, it’s always a good idea to keep a variety of physical currencies stashed away in a safe or hidden in a secure place for emergencies.

Connectivity

So, why am I bringing up connectivity in a post about money? Because most people don’t realize how closely linked their finances are to their phones until it’s too late.

Every time something goes wrong with your money—fraud, a locked account, or a simple transaction dispute—you need to make calls. Long fucking calls. Calls where you are on hold for 40 minutes, get disconnected, and have to start over. If you’re doing that on a standard Canadian carrier plan from abroad, you are getting gouged twice: once by the problem, and once by the phone bill while you’re solving it.

So, through pain and frustration, I’ve discovered some great options for the Canuck and Yank alike:

Fizz Mobil

This was a game-changer. Fizz is a Canadian Mobile Virtual Network Operator (MVNO; a smaller carrier that runs on an existing network) with pay-as-you-go options that don’t punish you for using your number internationally. The setup fee is minimal, the monthly cost is low, and since I have data turned off and don’t make outgoing calls on that number, I’m paying close to nothing each month. The number exists for one reason: to receive SMS verification codes from financial institutions and other platforms that require 2FA. Many online entities still don’t recognize Belizean phone numbers—even Google— so a Canadian phone number is critical for me. $10 to set up and $6 month is all it costs to receive texts and calls globally. It’s perfect.

YADA Phone

After Skype shut down its consumer service, I needed a VoIP replacement for the occasional calls to Canada and the USA. YADA Phone is desktop-based, costs cents per minute, and offers decent call quality. It’s not glamorous. But when you’re on hold with a fraud department for the third time that week, knowing the call costs almost nothing changes your entire relationship with the situation. You can hang up and call back without flinching.

Dual SIM Setup

I now use a dual-SIM phone: my local Belizean number on an eSIM with my Canadian number on the physical SIM. Both are live. Both receive incoming communications immediately. This sounds like a small thing until you understand my old setup: a busted-ass backup phone that I’d have to fire up every time I needed a Canadian 2FA. It was slow to connect and prone to code timeouts. Believe it or not, that was an upgrade to the previous method, which required me to store my Canadian SIM safely and swap it with the Belizean SIM whenever I needed to receive codes. I would occasionally misplace the SIM card or the tiny key needed to extract it, resulting in a cumbersome, stressful UX. The dual SIM was quick to set up with a marginal fee and has eliminated an entire category of friction for me.

What I’d Do If I Were Moving Abroad For the First Time

So, for the green expat or someone planning to make a move abroad, I’d recommend the following:

1. Get a Fizz (or equivalent) SIM before you need it. Seriously. It costs almost nothing to keep active, and having a live Canadian number that isn’t burning $100+/ month just sitting there is the kind of thing you’ll be glad you did when you’re standing in a bank queue in a foreign country trying to verify your identity.

2. Set up a Wise (or equivalent) account before you leave. A must if you earn anything online. The currency conversion savings alone—and I do mean savings, not a marginal rounding difference—will more than cover the time it takes to get verified.

3. Switch to a dual-SIM phone before you move. The old “backup-beater-with-a-home-country-SIM” setup created more problems than it solved. A modern dual-SIM phone with an eSIM for your local number removes all friction.

And honestly? Don’t wait for a crisis to build redundancy. I built most of this setup reactively because I was forced to. But it pays not to do it that way. The peace of mind alone is well worth the effort.

A Simple Financial Access Redundancy Plan

If you want a starting point, here’s a rough framework based on what I actually run:

Layer 1: Primary access (daily spending)

• Standard bank from your home country or an equivalent online bank, with a debit card, because it takes time to transition, as local bank accounts aren’t always available to foreigners.

• Wise or Revolut account with a card for international spending and receiving payments if you’re a remote operator.

Layer 2: Backup access (if Layer 1 fails)

• Local bank account with local card (wherever you’re based, but this often requires residency or specific visas, which takes time, and why it’s a layer 2 item)

• WealthSimple for savings, emergency funds, and investing. Connect it to Layer 1 financial institution so you can transfer money if your bankcard goes AWOL.

Layer 3: Emergency fallback

• ShakePay or equivalent for mobile tap payments.

• Physical cash: your local currency + USD at a minimum.

Connectivity foundation (runs under all of it)

• Local mobile service.

• Fizz (or equivalent) for your home country number and 2FA reception.

• YADA Phone or equivalent VoIP for long outgoing international calls.

• A dual SIM phone, so both numbers are live and immediate.

The specific tools matter less than the principle: every layer should be accessible independently. If you somehow lose both accounts in Layer one, Layer 2 works. If Layer 2 becomes compromised or a blackout causes L1 and L2 to fail simultaneously, Layer 3 is there to support you. Just ensure that once set up, nothing depends entirely on anything else. They can all be linked, but one aspect should never explicitly rely on another.

One More Thing

If you want to go deeper on this—the move, the setup, and the things nobody tells you before you leave—I talk through a lot of it on Foreign Radio and on Simo’s Substack. I’m all for helping people who are planning or navigating a life abroad, without the hype; just gettin’ real about what it actually takes.

You can also check out The Moving Abroad Punchlist for a practical pre-move checklist, and The Moving Abroad Reality Check if you’re still weighing whether a move abroad is actually right for you.

And if you are still in the planning stages or still trying to decide where to go, check out MoveSmart for personalized country matches that fit your life.

I hope you found all this helpful. And remember, there isn’t a one-size-fits-all solution here. Pick and choose what you want; you’ll figure out a version of this stack that works for you. But the sooner you stop assuming your home setup travels with you, the less it’ll cost you; in money, in stress, and in time spent on hold.

You got this.

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Got questions? Drop them in the comments; I read everything. And if this was useful, consider subscribing. New posts go out regularly, and they’re all trying to do the same thing: make your move abroad less of a gamble.

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Want more practical frameworks for making your move abroad smoother? Check out MoveSmart to help identify where your communication style might work best, or grab the Moving Abroad Punchlist for systematic planning without the hype. And if you’re curious about more real-world expat insights, you can catch full conversations like this on the Foreign Radio podcast.

Most people approach international relocation with excitement and a Pinterest board: beautiful beaches, charming cobblestone streets, impossibly cheap wine. They Google “best countries for expats,” make spreadsheets of visa requirements, and dive deep into cost-of-living comparisons.

And that’s all good stuff, except it’s missing an important factor: reality.

They find out the climate doesn't suit them (the case for many expats in Belize who enter their first summer in the Caribbean), or that the healthcare isn’t the quality they expected. They feel isolated in their expat bubble, which compounds when they realize that the local time zone makes it impossible to stay connected to family or maintain their remote work schedule.

Within two years, many are either miserable or have moved home.

The problem isn’t that they didn’t research enough; it’s that there is so much to research that they researched the wrong things. They optimized for their expectations and a rose-colored destination rather than an actual life fit.

But there is a way to tackle this meaningfully: understand yourself systematically before you fall in love with a place you can’t actually live in.

Moving Abroad Is Life Design, Not Destination Shopping

When my family moved to Belize in 2022, we thought we’d done our homework. We’d researched visa requirements, housing costs, and expat communities.

We had “a plan.”

What we didn’t have was a framework for understanding what we actually needed to thrive. So, we figured that out the hard way, through a bacterial infection that nearly killed our infant son, serial bureaucratic hairpulling that tested our patience, and social isolation and career pivots that strained our marriage and finances.

We made it work, but barely at times. And through conversations with dozens of other expats, I’ve realized our experience isn’t unique. Most people who struggle abroad didn’t pick “bad” countries; they just picked countries that were bad for them.

And the difference comes down to self-knowledge.

Relocation isn’t a geographic decision so much as an exercise in life design. Skip the self-reflection step, and you’re setting yourself up to discover your dealbreakers in a very expensive way.

The 25-Question Framework That Changes Everything

Below are the 25 questions that should guide every international move. Each question exists because I’ve seen what happens when people fail to answer them.

They’re practical filters that eliminate heartbreak and wasted time. I’ve broken them down into groups, which I call Phases, so you can easily skim or revisit them later.

Phase 1: Four Foundational Questions

These four questions are mandatory. Do not skip them! They frame everything else.

1. What’s triggering your move right now?

Your reason for leaving shapes where you should go. For example:

• Are you escaping political instability? Then you need somewhere with a history of peace and stability.

• Are you burned out from corporate life? Then a high-energy business hub like Hong Kong probably won’t fit.

• Are you retiring early? Then, long-term affordability becomes critical.

The trigger reveals what you’re actually optimizing for, which is often different from what you think you want.

2. Are there any major constraints you should keep in mind?

Think: Health conditions, family needs like schools, a house you need to sell or rent?

Constraints eliminate options faster than preferences add them. A child’s medical condition might rule out countries with limited specialist care. A mortgage might lock you into a timeline. A partner’s career might require specific visa types.

Most people don’t surface these constraints until they’re deep into planning…for the wrong destination.

3. How do you define a successful relocation for yourself?

Many people think that “living abroad” is the goal, when in reality, it’s a logistical state. Success might mean your kids are thriving in school, or you’ve found a creative community, or you’ve cut your monthly living costs by $2,000/month. Without defining success upfront, you’ll inevitably optimize for the wrong metrics and feel like something’s missing even when the move “works.”

4. How long do you plan to be away?

1-2 years? 5-10 years? Undetermined? Or, perhaps you never want to return.

A one- to two-year sojourn has different requirements than a permanent relocation. Short-term means you can tolerate inconveniences, while long-term means you need to invest in integration, like learning a new language, building community, and truly understanding the nuances of the host country’s bureaucracy.

Your timeline changes, which compromises are acceptable.

Phase 2: Five Questions for Designing Daily Life

These next questions shape your day-to-day experience more than any visa benefit or tax advantage.

5. What kind of lifestyle setting do you prefer?

Are you a city dweller, suburbanite, or a country-dumpkin?

Urban people wither in rural isolation; rural people suffocate in dense cities. This is different than vacation preferences! It’s about where you’ll potentially spend hundreds, if not thousands, of ordinary days. You need to be honest with yourself; separate who you really are from an idealized version of yourself.

This may seem obvious, but you’d be surprised by how many people I’ve met who have only lived a suburban life but are “itching to move off-grid” in rural (read: jungle) Belize. It rarely works; the harsh reality of that life quickly bears down on them, and the city-slickers slink home, hopefully without having dumped their life savings into a land purchase they thought they wanted when they were dreaming of a jungle life.

6. How important is walkability?

Think: Being able to walk to cafes, shops, and daily errands. Walkability goes beyond convenience into social infrastructure. Walkable neighbourhoods mean casual encounters and incidental community. Car-dependent areas often bring a subtle isolation, especially if you don’t speak the local language well.

7. Do you plan to own a car, or would you prefer public transit and walking?

Car ownership abroad is complex: import duties, local regulations, insurance, and the nuances of driving culture. Some countries, like Belize, make this relatively easy; others make it a bureaucratic nightmare. From what I’ve read, most foreigners in Costa Rica need to hire a lawyer for vehicle purchase and registration.

8. What’s your ideal climate?

This question is more important than you might think, and it's a harder one to answer than most people realize. Who doesn’t love the heat of a tropical beach community when on vacation, right? Sure, but can you take the heat all year-round? Ask yourself what climate you truly enjoy: Cool all year, hot and humid, dry heat, or four seasons?

Climate affects everything: energy levels, health conditions, social patterns, housing and utility costs, and outdoor activities. People consistently underestimate how much a climate mismatch drains them. “Can you take the heat?” has a harsh, practical meaning in tropical places.

9. What kind of natural environment calls to you?

Similar to climate, but different: Mountains, coast, forests, lakes, and plains?

When we moved to Belize, we wanted to be closer to nature. For us, access to nature wasn’t a luxury but a necessary psychological anchor. Mountain people need mountains. Ocean people need the coast. Landlocking a coastal person creates a subtle, persistent homesickness that compounds over time. That’s one of the reasons my family and I drove to Belize: unprecedented access to water we couldn’t achieve even when living in communities along Lake Ontario.

Phase 3: Cultural Fit

These determine whether you’ll feel at home or perpetually like an outsider.

10. How important is a vibrant, creative, or cultural scene?

If art, music, or intellectual culture is central to your identity, moving somewhere without it creates a void that no beach or low cost of living fills. I’ll admit, Belize lacks this, and it's a challenge for my wife, who’s a fine artist. Cultural scenes also indicate the presence of like-minded people who are potential friends and community members.

11. What are your safety and comfort requirements?

Some countries have rough areas, but are perfectly safe in many areas; Mexico, I’m thinking of you here. Others are statistically safe but feel uncomfortable. Your tolerance for ambiguity is personal, and if you’re moving with family, their comfort matters as much as yours. It’s important to remember that some degree of crime exists in most places, so this question asks you to reflect on what your exposure tolerance is.

12. Do you prefer a more progressive or traditional environment?

Think: Social norms, religious adherence, and pace of change?

A politically progressive person in a deeply traditional society (or vice versa) will feel constant friction. This isn’t about right or wrong but personal fit. I have some alternative-culture friends who live in a predominantly Mennonite community in the jungle. While most politely keep to themselves, there is a subtle clash of cultures that exists there. They’ve made it work, but it’s important to remember that you want to live somewhere your values don’t put you in daily conflict with the culture around you.

13. What kind of community are you looking for?

Are you drawn to an expat hub, local neighborhood, or blended international scene?

Expat bubbles offer easy friendships but shallow integration. Local neighborhoods offer depth but require language, effort, and the willingness to feel like an outsider for an indefinite amount of time. Blended scenes split the difference. While there’s no right answer, there’s a right answer for you. Find it early, and factor it into your country selection.

14. What’s your preferred pace of life?

High-energy people get bored in sleepy towns. Slow-paced people burn out in frenetic cities. Your nervous system has a set point, and fighting it is exhausting. Match your pace to the place. For us here in Belize, we can get a bit stir-crazy at times, as the “go slow” attitude can feel uninspiring at times.

15. What kind of feeling are you looking for in your new home?

This is the intuitive check. While data and criteria matter, you can’t forget the gut check. When you walk down the street, what does “home” feel like? This question captures what spreadsheets can never calculate.

Phase 4: Communication & Connection (Questions 16-18)

16. What’s your primary language? Do you speak any others?

Your existing language skills open or close doors. Fluent in Spanish? Latin America becomes easier. Even a basic understanding of another language gets a foot in the door and establishes confidence when engaging in another culture’s mother tongue.

No second language? You’re more dependent on English-friendly destinations, which limits options.

17. Are you willing to learn a new language?

This is a follow-up question to the one above: Language learning is a multi-year commitment that affects daily life, social depth, and professional options. If you’re unwilling to learn, you need countries where you can function without the local language, and accept the integration ceiling that creates.

18. What’s the maximum time difference you can tolerate?

Moving abroad often means time-shifting your relationships. If your aging parents are in New York and you move to Thailand, “quick calls” become logistically complex. Some people can manage 12-hour offsets; others struggle with 6.

Moving to Belize didn’t really affect our time zones much; 1-2 hours, depending on daylight saving time. I also predominantly work with North American clients, and Belize in CST sits nicely between the East and West coasts. But years ago, one of my brothers lived in Hong Kong, and while we kept in regular touch, we had to get used to chatting in the early morning or late evening to accommodate the 12-to-13-hour time difference.

Phase 5: Practical Reality

The non-negotiable logistics that determine whether your life actually works.

19. What’s your target monthly budget in USD?

Budget determines your tier of experience. $2,000/month in Lisbon is a very different life than $5,000/month. Knowing your number filters the map quickly.

20. How important is access to high-quality healthcare?

If you have ongoing health needs, healthcare access isn’t optional. Some countries have excellent public systems, such as Singapore, Sweden, and Japan, while others rely on expensive private systems. If you have specific medications you need regular access to, knowing if they’re available in your host country is essential, as some aren’t available everywhere. This is a common concern for foreigners in Belize, and importing medications from your home country can be expensive and time-consuming.

21. How important is high-speed, reliable internet?

If you work remotely as I do, the internet is your lifeline. It’s beyond a utility or a country’s infrastructure. It determines how you show up and operate in the business world. Unreliable connections mean missed meetings or deadlines, losing potential clients, and untold stress. Some destinations look idyllic until you realize the wifi can’t handle a Zoom call, and it’s easier to make a trade-off in the planning phase than to pivot once abroad.

22. Are you looking for short-term, medium-term, or permanent residency?

Visa types match intentions. Tourist visas work for 30 to 90 days, while digital nomad visas may extend stays for 1-2 years. Residency-by-investment works for more permanent moves. Mismatching your intention to the visa creates instability.

23. Do you have any visa advantages?

Think: Existing citizenships, ancestry claims, or golden visa eligibility?

Your passport and heritage unlock hidden doors. Irish grandparents? You might qualify for EU citizenship. Most people don’t inventory their advantages until it’s too late.

24. Will you need to ship belongings?

Shipping internationally is expensive and complicated. If you’re attached to furniture or equipment, some destinations become logistically painful. Traveling light opens more options but may leave you repurchasing items you previously sold at fire-sale prices or put in storage before leaving. It’s a delicate balance to strike: we simultaneously wondered why we brought one item to Belize while cursing ourselves for leaving another behind.

While I love my dogs, this is a good place to ask whether your furry family members are coming along. They are more than possessions, but when it comes to international relocation, they are often treated as commodities that require import permits and lengthy bureaucratic processes.

25. Is there any place you definitely don’t want to live?

Everyone has dealbreakers. Naming them upfront prevents wasted time exploring options you’d never actually take. If you want to extricate yourself from the mass consumerism of US culture, moving to Canada probably isn’t the best bet.

Why This Framework Changes Everything

Most people skip half of this list; I honestly can’t say I systematically ran through it before I moved to Belize. They Google, search YouTube, and scroll TikTok or Instagram, pick from whatever listicle appears, and then join a bunch of Facebook groups to ask questions and receive snarky answers. Then they wonder why they’re unhappy six months in.

These 25 questions exist because international relocation is more than a location consideration; it’s an exercise in life design. The right country isn’t objectively “best” but subjectively best for you, given your constraints, your values, and your vision of success.

When you approach moving abroad this way, you stop chasing other people’s Instagram reel dreams and start building your own life. You choose your trade-offs instead of inheriting random struggles from others' decisions. That’s the difference between surviving somewhere new and actually thriving there.

If you answer these questions honestly, you won’t just find a place to live, but a place where your life actually works; a place to call home.

Now What?

So you’ve answered the 25 questions. You know you need walkability, can tolerate a 6-hour time difference, and won’t survive anywhere without mountains.

Great! But you now have a profile of your ideal life abroad sitting in your head, and no systematic way to match it to an actual place. Most people take their carefully considered answers and... Google “best countries for expats” again. They join Facebook groups, post their criteria, and receive a flood of contradictory advice from people who’ve never asked themselves these questions at all.

The answers are the hard part. Finding the match shouldn’t be.

That’s why I built MoveSmart. It systematically walks you through questions just like these, then maps your answers to destinations that actually fit your criteria; no hype, no affiliate links to random visa services, just the honest match between who you are and where that person can actually thrive.

If you’re not ready to dive in, you can also grab the Moving Abroad Punchlist for the logistics side, or read The Moving Abroad Reality Check for the unvarnished truth about what the first few years actually feel like.

And if you want to go deeper on the themes behind these questions—language learning, life reinvention, global perspectives, location-independent careers—I explore all of it on my podcast, Foreign Radio.

If you enjoy this, you might also like Foreign Radio Podcast, A Foreign Perspective, Foreigner501, Foreign Tales, the Lili Art Blog, or my award-winning book Home in Good Hands. If you’d like to support this Substack and help me keep creating stories and essays about life abroad, consider subscribing, sharing, or buying me a coffee. And to those who already have—thank you. Your support means the world.

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MoveSmart’s Country Finder provides valuable analysis, and beta testers get early access to AI-powered country matching, plus a free personalized report.

Here’s something that’ll make you want to throw your laptop across the room: I recently saw someone in a move-abroad Substack Note tell people to “pick the wrong country on purpose because it’ll teach you a lot and you can just move again.”

This has got to be some of the worst advice I’ve seen in the expat community in a long time.

Moving abroad isn’t like rearranging furniture in your living room. It’s more like pouring a foundation for a new home and the next chapter of your life. Once the concrete sets, you’re building everything else on top of it: your golden years, or your kids’ schooling, your career, or community, and your daily rhythm.

Start with the wrong foundation, and everything you build on it is compromised.

As someone who moved to Belize with my wife, two kids under 18 months, and two dogs, I can tell you from personal experience that another international move wasn’t something we could just shrug off and do again.

We were tapped out, utterly exhausted from all the effort; it was quite the ordeal.

And like us, many people liquidate their lives when they move abroad. They sell cars, belongings, and homes. They ship valuable goods internationally. This isn’t something you flippantly undo.

I’ve witnessed the revolving door of foreigners in Belize firsthand. When people leave because they couldn’t make it work, it’s often devastating in many ways.

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Why Country Research is Broken

Here’s the reality: figuring out which country fits your life is genuinely hard, and picking the wrong one can be an expensive, time-consuming mistake.

You can spend months reading forums, Reddit threads, and diving into the vast world of “expat-stack” and still end up with conflicting information, opinionated advice, and analysis paralysis. The “Portugal is paradise” crowd battles the “Portugal is overrated” faction while you sit there wondering which one applies to your situation.

Or you can pay a relocation consultant $5,000+ for a “personalized assessment” that often amounts to a handful of calls, a workbook, and some PDFs, with no real analytical framework behind the recommendations.

The gap between these options is massive. Most people need something more systematic than diving into months of Facebook country groups, but less expensive than hiring a consultant who may or may not understand your specific constraints.

What We Built

That’s why I’m recruiting 10 beta testers from my Substack audience to try MoveSmart before the public launch!

MoveSmart is an AI-powered relocation assistant built around Hermes, a conversational AI that walks you through 26 structured questions covering everything that actually matters when choosing a country:

• Your lifestyle preferences and pace-of-life needs

• Climate tolerance and seasonal preferences

• Budget realities and cost-of-living constraints

• Family situation, kids’ schooling, pet considerations

• Healthcare needs and accessibility requirements

• Career setup and remote work logistics

• Timezone constraints and travel frequency

• Visa realities and residency pathways

• And intangibles, like what “feeling at home” means to you

Unlike generic “best countries for expats” listicles, Hermes listens, remembers your constraints, and generates a personalized shortlist of 3 countries tailored specifically to your life, not someone else’s opinions.

The experience is intentionally conversational and not a cold, static web form. Relocating is emotional, and we designed Hermes to acknowledge your responses, ask follow-up questions, and make you feel more like talking to a knowledgeable friend than filling out paperwork.

Who This Is Actually For

MoveSmart serves people across a spectrum, from daydreamers to those actively planning logistics. If any of these describe you, then you will benefit from the beta test:

• You’re exploring where to move, but are overwhelmed by options

• You have real constraints: kids, pets, health conditions, remote work requirements, or a home to sell

• You want clarity without the sales pressure of relocation consultants

• You need a thinking partner to do some of the heavy lifting and help narrow your focus.

MoveSmart isn’t for people hunting tax loopholes, visa hacks, or a guru to make decisions for them. It’s for people who want to make smart, informed choices themselves.

How the Country Finder Works

1. Start by clicking “Find me a country”: Hermes begins the intake and walks you through twenty-six structured questions, one at a time, with a progress bar to show exactly where you are in the process.

2. Get your matches: After the intake, Hermes generates your personalized shortlist of 3 countries with:

   1. A brief country summary of why each country fits your criteria

   2. Specific cities and regions to explore

   3. Potential dealbreakers to verify before you get too excited

3. Download your report: Walk away with a comprehensive PDF that includes your analysis of the criteria, regional recommendations, and next steps for deeper research.

The whole process only takes 15-20 minutes, even if you’re thoughtful with your answers.

What Beta Testers Get

As a beta tester, you’ll receive:

• Full access to the Country Finder experience

• A personalized country report, the same PDF that will eventually be a paid feature (you can see an example report in the Loom video).

• Special beta discount when we launch Phase 2 features

• The satisfaction of shaping the product; your feedback directly influences what gets built next

Beta Tester Requirements

In exchange, I ask that you:

• Complete the full experience within 72 hours of starting

• Fill out a short feedback questionnaire afterward (5-10 minutes)

• Be honest, critical feedback is more valuable than polite feedback

• Actually follow through (that’s why there’s an application process)

What’s Coming Next

Just like picking the right country before you move lays the path for the next phase of your life, Hermes and the Country Finder flow is the foundation for MoveSmart.

Here’s the roadmap:

Phase 2 features (in development):

• Generate a relocation plan: Structured, phased checklists covering everything from selling your home to arrival logistics based on the comprehensive report.

• Reality-check a country: Already have a destination in mind? Hermes will pressure-test your choice and flag potential blind spots

Future additions:

• Side-by-side country comparisons

• Deep-dive modules for healthcare, schooling, and visa pathways

• Cost-of-living calculators for your target cities

• Community forums for connecting with others making similar moves

MoveSmart is designed to be the tool I wish existed when I was figuring out my own move to Belize. This beta is the first step in making it real!

Want to Help Shape the Future of Country Selection?

Watch a Loom walkthrough below and then visit movesmart.world

My goal isn’t just to surface bugs but to ensure we’re building something that actually solves the country research problem without the overwhelm or the consultant fees.

You got this!

Let’s figure out where “this” should happen.

MoveSmart Walkthrough

If you’re not ready for beta testing but want to stay updated, subscribe below. And if you’re already deep in move-abroad planning, check out The Moving Abroad Punchlist for systematic logistics without the chaos.

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Quick Note: I am not selling anything here; on the contrary, I’m giving something away for free.

Three years ago, as part of my move to Belize, I changed careers. On paper, I had plenty of experience, but in reality, I didn’t have a clean way to explain it in a new context. I knew I was capable, but every attempt to translate my background seemed to land in one of two places: too vague to be credible, or too elaborate to stand out.

If you’re planning to move abroad (or even seriously considering it) but aren’t ready to retire, there’s a practical problem that quickly shows up:

Your desire for portable income is blocked by a credibility gap.

This was a real shock to my system. As someone who’d been self-employed for a decade-and-a-half, I figured I could finagle my way through it. And while I did, it was frickin’ painful. What surprised me most was how disorienting it was. I felt unmoored. I lacked direction because I didn’t have a clear understanding of how my previous work experience could translate to a remote setting (for context, I ran my own residential renovation business in Canada). After years of working for myself, I’d forgotten that a career transition is less about a skills gap and more about clearly framing and translating your current skills into a new context.

That gap is what led me to build the Career Pivot Lab: An agentic career transition tool designed to help people pull real transferable skills out of their past work and turn them into practical career assets they can actually use:

• clear positioning based on high-level skills

• role-fit ideas based on those skills

• resume bullets that reflect this new context

• LinkedIn bio direction + proof points

It also supports job searches for your target role, applications, and interview prep.

The agent is a culmination of my personal experience with a career transition and the last 3 years of working closely with LLMs, developing and using prompts that produce more than just content. Honestly, I wish I had a tool like this when I first made the change. Even still, testing the agent with my own work experience has given me newfound confidence, revealing a previously unrecognized thread that runs through everything I do. It connected dots in a way I couldn’t because I was too embroiled in my lived experience.

I now see myself as:

“a systems-first operator who’s spent two careers doing the same thing in different mediums: turning messy inputs into clean plans, and clean plans into finished deliverables. I build repeatable workflows, manage stakeholders, and ship high-quality work, from proposal and production through QA and publishing.”

And it’s right: that’s not some syncophantic AI slop. It’s a real thread that characterizes how I work and show up every day.

I really believe in this tool and know it can help others just like me who are facing challenging career transitions, whether they chose them or not.

Right now, I’m running a small beta test of the agent, and I’d love a few more testers to join. My first thought was to reach out to this community, especially people planning a move and who will need work lined up (or a clearer strategy) on the other side.

A current beta tester summed up their agent experience like this:

“Hey Simo, LOVING the tool so far! I’m still working my way through it but I’ve been really impressed so far :)”

And don’t worry, this isn’t about collecting data from participants; I don’t have access to that side of things. This is about getting feedback on agent interaction and output quality; blunt feedback on what was genuinely useful vs. fluffy, what was confusing/too long, and what you’d change to make it better.

If you want to join the beta group, please comment BETA below or message me in the Subscriber chat I’ve set up, and I’ll DM you the link and instructions.

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And if you don’t need it personally, I totally get that, but feel free to forward this to someone who’s in a transition (especially if a move abroad is part of the plan).

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Best, Simo

Image by twg studyabroad from Pixabay

In 2022, my wife and I sold up our comfortable, predictable life in Canada and moved to Belize with two small kids and two dogs. We walked away from established careers, a home we’d poured ourselves into, family support, and every system we knew, in exchange for heat, humidity, uncertainty, and the possibility of a very different kind of life.

Since then, we’ve built a home from scratch in a foreign country, established new income-generating systems, and figured out how to raise kids without grandparents around the corner or Amazon Prime filling in the gaps.

None of this was a “digital nomad experiment” or a three-month sabbatical. It was a full-scale life change with real risk attached. I’ve written about the actual costs of living abroad, the logistics of getting your stuff and your family across borders, and the emotional messiness that comes with leaving the script.

The following is the high-level roadmap I wish I’d had when we were making spreadsheets at midnight and wondering if I was completely out of my f’in’ mind.

It’s a practical, no-fluff list of steps that lay out what to do after you first say, “Okay, we’re moving abroad… but how do we actually do it?”

---

Read this Before Anything Else

A practical roadmap from “I need out” to landing softly in your new life.

I don’t want to scare you, but moving abroad is challenging. There are a lot of moving parts and balls to juggle. So, I created this guide in the hopes that it will make things easier for you.

1. Start With How You Want to Live (Not Where)

If you have no idea where you want to go, just that you want to leave, start here.

List out how you want to live day to day:

• Pace of life (slow/coastal vs. big-city energy)

• Climate (dry heat, tropical humidity, four seasons)

• Cost of living (lean and simple vs. more comfortable but pricier)

• Community (tight-knit village vs. anonymous city)

• Access needs (healthcare, airports, specific amenities or hobbies)

As I showed in my Belize Expat Living Expense Report, there isn’t one “expat budget.” You can live very cheaply or quite expensively in the same country, depending on how you set things up.

So design the lifestyle first, then match the country to it, not the other way around.

Create a shortlist of countries by plugging in my AI Country Match Prompt to your favourite model (ChatGPT, Claude, whichever).

Just copy and paste the prompt, fill in the preference fields (budget, language, climate, family situation, work style, etc; they’re all provided), and it will give you a shortlist of countries that match the life you’re trying to build.

It won’t magically pick your future home for you, but it will give you a realistic menu to research instead of staring at a world map and wondering where to go.

2. Get Real About Income and Work (Before You Pack Boxes)

Before you disappear down a rabbit hole of “Best Beach Towns for Expats” videos, you need to answer one unsexy question: how is money actually going to work?

A. Know what kind of income you’re relying on

Each path comes with different risks:

Remote Job

• Steady paycheque, but you’re tied to someone else’s business.

• Time zones matter: late-night calls and early-morning meetings can quietly wreck your quality of life.

• But, check whether your employer is even allowed to have you working from another country.

Freelance / Business Income

• Flexible and portable, but not always steady, especially at first. (I know this firsthand and still live it, nearly 4 years in).

• Expect a dip in productivity and revenue while you move, get settled, and rebuild your routines and processes.

Local Work

• Often pays far less than you’re used to, especially in lower-cost countries. For example, the average wage here in Belize is USD 2.50 per hour.

• May require language skills, local qualifications, or specific visas.

• Don’t assume you can just “pick something up when you get there.”

Savings and Runway

• How many months could you realistically cover your basic life abroad with no income coming in?

• Be honest about this number; it’s your real risk profile, not your “everything will work out” gut feeling.

Most people use a mix of these, but one typically does the bulk of the earning. Get clear on which one it is and plan to keep it alive and kicking.

B. Align your work plan with the visa reality

Visas and income are often joined at the hip (definitely the case in Belize):

• Some visas assume you’re bringing in foreign income and not working locally.

• Others require local employment, a minimum salary, or a specific type of investment.

• Most countries require proof of income or savings when renewing tourist visas or applying for some form of residency.

Make sure your income plan doesn’t quietly break the rules of the visa you’re banking on.

C. If you’re moving as a couple or family

This is where things get tricky:

• One person often becomes the “portable income engine” while the other ends up handling kids, school, and life admin, at least for a while.

• A partner might have to give up their career, credentials, or earning power in the short term, which isn’t a small sacrifice.

• Factor in childcare costs and availability; you can’t “just work online” with toddlers climbing all over you 12 hours a day—trust me on this.

Talk through this honestly with your spouse or partner now, not when resentment shows up six months into your move.

D. Build a boring financial buffer

Moving abroad is exciting, but your money situation shouldn’t be.

• Aim for a buffer of several months of lean living expenses in cash or easy access accounts—ideally six or more, but at least some cushion.

• Assume you’ll have surprise costs: visa runs, deposits, car repairs, “we didn’t think of this” paperwork fees.

• Keep in mind that your income may (will) stutter during the move and for (potentially) an undefined amount of time after you move abroad.

The more boring and predictable your work and income are, the more flexibility you’ll actually have once you land.

3. If You Already Have a Country in Mind

If you’ve already got a strong “pull” towards a specific country, your next step is research; real research, not just watching montage reels of palm trees on TikTok or Instagram.

A. Facebook groups (yes, really, and I know, cringe)

Facebook is still where a huge chunk of the world organises life, especially Xennials, Gen Xers, and Boomers.

• Search for “Expats in [Country/City]” and join a few groups.

• Use the search function before posting (e.g., “shipping costs,” “schools,” “electricity bills,” “visas”) to avoid crumudgeony replies.

• Once you’ve read existing threads, ask specific follow-up questions.

Just be prepared for:

• Trolls: There will be shit-posters. Don’t let them get to you. Ignore them and focus on the genuine replies, which also exist.

• Newly arrived experts—Armchair expats, as I like to call them—with strong opinions and very little long-term experience.

You’re not looking for one perfect answer; you’re looking for patterns that show up across many responses.

I’d suggest copying and pasting anything useful into a Word/Google document or spreadsheet, then running it through an LLM to distill the info into usable and organized chunks. More on that in a later post.

B. YouTube research (handle with care)

YouTube can be helpful, but it’s also full of:

• Sensationalized content (“$500 a month LUXURY LIFE ABROAD!”)

• Clickbait titles that never answer the actual question

Focus on videos that cover:

• Cost of living (broken down by housing, utilities, food, transport, schooling). If you are interested in Mexico, check out Marc Andre from More Life Diaries

• Best places to live “like a local” vs. classic expat pockets

• Visa options and requirements (tourist extensions, investment visas, digital nomad schemes, etc.)

• Length of stay allowed, required proof of funds, and any conditions (e.g., monthly income, savings, or local investment)

• For families: schools (public, private, international), daycare options, and realistic kid activities

Filter hard. If every video looks like an advertorial for the creator’s relocation service, treat it as marketing, not neutral information.

C. Check lifestyle fit and your non-negotiables

Ask yourself:

• Do my hobbies and passions exist there in a real, everyday way?

• What will I do on a random Tuesday afternoon when I’m not on the beach or doing tourist things?

• If I have kids, will they have age-appropriate activities and peers?

You’re not trying to prove the move is perfect. You’re looking for obvious misalignments before you uproot your life.

D. Talk to real people and plan a “soft landing”

Reach out to people online and see who’s open to meeting when you visit. A coffee with someone who has lived there for 5+ years is worth more than ten “Pros and Cons of Moving to X” videos.

On my podcast episode with Queen D Michele, she talked about “soft landings”; doing enough research and relationship-building ahead of time that you’re not hitting the ground completely alone.

That might look like:

• One or two local contacts you can message with questions

• A recommended neighbourhood or two to focus on

• A sense of where expats like you actually live, work, and shop

4. Do an Exploratory Visit (And Don’t Treat It Like a Vacation)

If you can swing it, an exploratory trip is huge.

Length:

In my conversation with Brian Clark, he suggested three months as a good minimum. That’s long enough to learn what life feels like beyond the tourist bubble.

Reality check:

For many people (including us), three months wasn’t realistic; newborn, 16-month-old, two dogs, location-based jobs.

So, do what you can: four weeks beats two, two beats one.

However long you’re there, don’t:

• Spend all your time at resorts

• Eat only in tourist restaurants

• Stay only in short-term rentals designed for week-long stays

Instead:

• Shop at regular supermarkets and cook your own meals.

• Walk or drive the neighbourhoods you might live in.

• Test the internet where you’d realistically be working.

• Pay attention to noise, traffic, and how you feel moving around day to day.

Think of it as a test run for your actual life, not a break from it.

Test your “location independence” before you move

If possible, run a small work experiment during this trip:

• Work remotely to see how your job or business actually performs.

• Try living on your projected budget for the duration of your trip.

• Notice what works (or doesn’t): sleep, focus, internet, communication with clients or your boss.

If the system collapses on a short trial, a permanent move won’t magically fix it.

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5. Once You’ve Chosen Your Country

Now we get into logistics.

Decide: seasonal resident or all-in move?

Your finances will largely decide whether you:

1. Keep a home base in your original country and live part-time abroad

2. Rent out your home and treat your host country as “home for now”

3. Sell everything and fully relocate

Whichever path you choose, every next decision flows from it.

6. If You’re Selling Up

If you’re going all-in and selling your current home:

Assess the house honestly:

• Does it need repairs, upgrades, or cosmetic work to sell well?

• Do you need a realtor to help you price and position it?

Factor in time:

• Renovations and touch-ups can take weeks or months

• The sale process has its own timeline (listing, showings, negotiations, closing)

You don’t want your shipping container ready before your house is.

7. Stuff, Shipping, and “Do We Really Need This?”

Once you know whether you’re keeping a base, decide what stays and what goes.

A. Figure out what you can buy locally

During your research and exploratory trip, pay attention to:

• Furniture and appliance prices

• Tool and hardware availability

• Electronics and replacement parts

Some things are cheaper locally; others are wildly more expensive or hard to find.

B. Shortlist what you might bring

• Big sentimental items

• Quality tools or gear that’s expensive to replace

• Things that are part of your livelihood

C. Get shipping and logistics quotes

Shortlist logistics companies and ask for detailed quotes for:

• Size/weight of shipment

• Door-to-door vs. port-to-port

• Insurance and handling

Expect a huge range. We were quoted anywhere from USD 1,500 to nearly USD 60,000 for “white glove” services when we sent a sea can from Hamilton, Canada, to Belize.

D. Compare replacement cost vs. shipping cost

If shipping your couch costs more than buying a new one where you’re going, the couch can probably stay.

E. Plan customs on both ends

Outbound: logistics to get your stuff out of your home country

Inbound: a customs broker in your new country to receive and clear your shipment

Duties and taxes on imported goods are often the biggest line item—plan for that, not just the shipping itself.

Have your logistics plan lined up to sync with your house sale or rental start date so you’re not living in an empty shell for months—or scrambling at the last minute.

For those interested in the logistics of my move to Belize, I wrote about it here.

8. Renting Out Your Home Instead

If you’re not ready to sell:

Decide what furniture and belongings tenants can use.

Everything else:

• Gets stored locally

• Or gets shipped abroad on a smaller scale

Create a simple manifest:

• What you own

• Its approximate value/replacement cost

• Where it is (box number, crate, container or if it’s in storage and not coming with you)

This makes insurance claims, customs paperwork, and future moves much less painful.

9. Money, Insurance, and a Realistic Cushion

Before you hit “go,” you need some rough numbers.

Expat insurance:

If you won’t have coverage through work or a local system, look into expat insurance. I’ve had AXA Global before, and it seemed pretty good, but there are lots of options these days.

As a ballpark, many plans land around:

• USD 1,000–1,500 per adult per year

• USD 500–1,000 per child per year

Actual numbers vary by age, health, and coverage level, but build something in.

Budget for your new life:

Start with your best estimate of monthly costs (housing, utilities, food, transport, schooling, insurance, visas, fun).

Be willing to adjust your lifestyle—most people need less than they think if they’re ready to let go of certain comforts.

Once you have your “number,” add a 20% contingency for:

• Visa runs

• Surprise fees

• Car repairs

• The “oh shit, we didn’t think of that” category, which is more common than you may think.

If the numbers don’t work, adjust the plan on paper first, not mid-move.

10. Set a Departure Date and Choose Your Route

If you’re selling your home, your departure date will usually be tied to:

• The closing date

• Or the start of a tenant’s lease

If you’re not selling, you have more flexibility—book your departure when the numbers and timing make sense.

Decide how you’ll actually leave:

• Flying: simplest, especially if you’re not transporting much.

• Driving: more complex, but it can make sense if you’re bringing a vehicle and gear.

• Combination: e.g., drive partway, ship partway, fly the rest. This is what I did when moving to Belize.

If you’re driving through other countries:

Research:

• Temporary vehicle import rules

• Required insurance (for example, Mexico requires temporary insurance and a temporary import permit, both with upfront fees)

• Any limits on what you can bring through in a private vehicle

Depending on how much you’re carrying, you may need a customs broker just to transit your stuff through a third country. (I’ll cover more of this in a separate piece about our On the Road in Mexico experience.)

11. Housing in Your New Country

Next, you need somewhere to land.

Short-term rental first:

Many people start with a 1–6-month rental in the area they think they want to live in.

This gives you breathing room to house-hunt without rushing.

Buying property:

This process is a whole separate beast—laws, title issues, financing, local quirks.

I’ll do a dedicated post on this rather than cram it into a single bullet point here.

Either way, make sure you’ve:

• Confirmed how you’ll get from the airport/border to your rental or new home

• Sent your arrival details to any landlord, agent, or friend who’s helping you

12. Welcome Abroad. Now What?

If you’ve made it through this punchlist, congratulations. You’ve already done more real planning than most people who casually say, “We should just move somewhere cheap.”

In future posts, I’ll go deeper into specific pieces: buying property, building a home abroad, school choices, earning online from a foreign country, and all the weird emotional stuff that doesn’t fit neatly into bullet points.

But for now, you’ve got a starting framework. Tweak it to your reality, run the numbers, ask hard questions, and then, if it still calls to you, start taking the first small steps toward your own “welcome abroad” moment.

Thanks for sticking with me through this punchlist. If there’s something I missed, or you’ve learned a hard lesson from your own move, add it in the comments so others can learn from it too.

And if you’re still in planning mode, I’d love to hear where you’re at in the process and what’s tripping you up right now.

Welcome abroad!

P.S. If you want something more practical than a wall of text, I’ve turned this punchlist into an interactive checklist you can copy into your own Google Drive. It includes every section, broken down into concrete action items with checkboxes to track your progress from “vague idea” to departure day. You can grab the editable version here.

If you enjoy this, you might also like Foreign Radio Podcast, A Foreign Perspective, Foreigner501, Foreign Tales, the Lili Art Blog, or my award-winning book Home in Good Hands. If you’d like to support this Substack and help me keep creating stories and essays about life abroad, consider subscribing, sharing, or buying me a coffee. And to those who already have—thank you. Your support means the world.

Photo by Greg Rosenke on Unsplash

The Question Everyone Whispers Eventually

At some point, quietly and usually late at night, most people entertaining the idea of moving abroad run into the same dead stop:

“If we left… where would we even go?”

I’m not talking the fantasy version, or the influencer montage version, or the SEO heavy “Top 10 Expat Paradises of 2025” articles written by someone who has never left their apartment.

I’m talking about a real answer; one that reflects:

• your work

• your comfort with risk

• your money

• your pace of life

• your kids (or lack thereof)

• your climate preferences

• your timeline

• your values

But the problem is there’s no tool built to handle all of that nuance.

So I built one.

It’s a simple fill-in-the-blanks AI prompt that generates a personalized shortlist of countries for your life.

This isn’t a quiz. This isn’t a BuzzFeed “Which Mediterranean Island Matches Your Aura?” test.
It’s an actual decision-making companion.

And the best way to use it?

Try it.
Seriously. Drop your answers in and see what emerges.

If You’re Already AI-Savvy, Skip the Foreplay

👉 Jump straight to the full prompt here.
(Scroll link to the prompt section below)

If you’re new to all this, keep reading — it’s straightforward and surprisingly fun.

Why This Prompt Exists (a bit of context)

A while back, when my wife and I were going through a particularly hard chapter, we began questioning whether Belize was still the right fit for our family. We weren’t looking for a vacation spot; we were trying to imagine an entirely new life.

I am an early adopter of LLMs. I use AI—heavily—to research, compare, analyze, and clarify almost everything I do.

And one thing has become apparent to me:

The answer you get from AI is only as good as the questions you ask and the information you provide.

So I refined the questions.
Then refined the structure.
Then, built a form anyone can use, regardless of how much you know about AI, visas, or geopolitics.

Then I tested it and refined it further.

The result is the prompt below.

And the answer it produces reflects your life in a very real way.

How to Use This to Find Your New Country

This is a fill-in-the-blanks prompt you can copy into ChatGPT (or any similar tool) to help you generate a shortlist of countries that fit the way you actually want to live.

Using the prompt is simple:

1. Copy everything under “MOVING ABROAD COUNTRY FINDER — CUSTOM PROMPT” to ***END OF PROMPT***

2. Paste it into ChatGPT (or other LLM, like Claude).

Remember, when on a desktop device, use <shift> <enter> when adding space so you don’t send the prompt prematurely.

3. Fill in all questions (1-16) with your own details; find this under “Here is my information” early in the prompt.

4. Choose how many countries you want in your shortlist (or let it default to three).

5. Use the results as a starting point for deeper research and, ideally, future scouting trips.

That’s it! No special tech skills required.

Remember: as with any LLM, the more info you can provide, the richer the result will be.

***COPY EVERYTHING BELOW THIS POINT, THEN FILL IN THE QUESTIONS***

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