Don’t Retire Abroad Until You Fix This
Fix This First
The one thing to sort out before you retire abroad, so your dream move doesn't turn into an expensive round trip.
There's a version of your retirement out there that most people never get to live. Not because it's impossible. Not because it's too expensive. Because they pack the wrong version of themselves into the suitcase.
I've watched it happen. People finally make the leap, move abroad, check every box on the spreadsheet, and a few months later something feels off. Plenty of Americans who retire overseas end up moving back within a few years, and it is rarely because the country let them down.
Retiring abroad is one of the best decisions you can make. I retired at 50 to test cities and islands across Southeast Asia, and I'd do it again tomorrow. But it works best if you fix one thing before you go. This guide walks through what that is, the traps that catch new retirees, and a simple four-part checklist you can start today.
01Moving abroad doesn't reset your life
Most people think retiring abroad is about picking the right country. Cost of living, visa options, health care. All of that matters, and I cover it in plenty of other episodes. But none of it is the real issue. ▶ 2:11
The real issue: moving abroad doesn't reset your life. It exposes it. Your habits come with you. Your routines come with you. Your mindset definitely comes with you, and it never pays for its own plane ticket. If something isn't working now, it won't magically start working because the view changed. ▶ 2:32
Here's the good news. Retirement abroad is one of the rare moments in life when you get to reinvent yourself. You're not tied to your old routine, your old identity, or even your old cost structure. You can design something new. You just have to do it on purpose, or you end up rebuilding your old life in a warmer place.
02Trap 1: no daily structure
Back home, your life came with structure built in. Work gave your day a backbone. Friends and family added the rest: Friday drinks with the crew, Sunday dinner, Tuesday night tennis or bowling. Retire and move abroad, and all of that disappears overnight. ▶ 3:24
Now you have real freedom, the kind people dream about for decades. If you haven't thought about how to use it, it turns into empty space. You wake up without a plan, drift through the day, and start wondering what you're doing. That isn't a location problem. It's a structure problem, and structure is fixable.
For me, this is still evolving. I started out focused almost entirely on diving. Now I've added this channel, pickleball and getting back into the gym, and each one adds a little more shape to my week. ▶ 4:50
03Trap 2: thinking travel equals fulfillment
At the start, everything is new: the food, the streets, the weekend trips. And that part is 100% real. Retiring abroad opens up a level of adventure most people never touch. You can wake up in a place others save for years to visit for a week, and often do it for less than staying where you are. ▶ 5:11
But adventure alone isn't enough, because eventually the new becomes normal. When that happens you're back to your day-to-day life, and it needs something deeper than sightseeing to give it direction.
04Trap 3: the social side nobody plans for
When you leave the US, you're not just leaving a place. You're leaving relationships that took a lifetime to build: friends who know you, shared history, connections that grew over years. There's an expectation that you'll replace all that fast. That's not how it works. ▶ 6:42
The balance that works:
- Get comfortable being alone. Not isolated, not cut off, just at ease with your own company. If you can handle that, you won't feel desperate.
- Stay open. Start conversations, try new places, say yes when an invitation shows up. Friendships here grow the same way they did back home: slowly, then all at once.
Many of the friendships I've made abroad started with locals and fellow expats who were kind enough to include the new guy. Showing up with curiosity and good manners goes a long way.
05Trap 4: escaping instead of building
A lot of people move abroad to get away from something: stress, burnout, frustration. That makes sense. But if you never define what you're moving toward, you land in the same emotional place with a nicer backdrop. ▶ 8:01
Be intentional instead. Decide how your days look, what matters, and what doesn't. That's not escape. That's design.
06Trap 5: losing your identity
For most of your life, your identity was tied to your career and what people expected from you. Then one day that's gone, and if you don't replace it with something intentional, you start to feel old. ▶ 8:49
This is also where the biggest opportunity lives. You get to decide who you are next. You're not starting over, you're building forward. Focus on your health, make something creative, learn the language, or finally chase the things you put off for years. Retiring abroad isn't just cheaper. It gives you room to become a better version of yourself, if you choose it.
07The four things to fix before you go
So what needs fixing before you book anything? Four things. ▶ 9:54
| Fix this | Ask yourself |
|---|---|
| 1. Your ideal day | Not a vacation day. A normal Tuesday. What does it look like when nobody tells you what to do? |
| 2. Your routine | How will you structure mornings, stay active and stay consistent? Freedom without structure sounds great until you live it. |
| 3. Your social plan | Where will you meet people? Which places put you around others naturally? |
| 4. Your purpose | What are you building, learning or improving? It doesn't have to be big. It does have to matter to you. |
Ready To Leap?
Tick each one you can answer clearly today. Your answers save in this browser, so come back as your plan grows.
08Try the one-week test before you book
Before you buy a single ticket, take one week and live your abroad life right where you are. No work. Plenty of free time. Intentional structure. See what holds up and what breaks, then fix those things at home and take the solutions with you. ▶ 11:53
Then, once the one-week test goes well, do the real version: a one or two month trial stay overseas. My Before You Leave checklist covers the practical side (phone number, banking, documents), and the Retirement Blueprint lays out the full step-by-step plan for the Philippines.
To paraphrase every superhero movie ever made: sometimes you have to take the leap and learn to fly on the way down. A little thought ahead of time never hurts, though. Capes are optional.
Frequently asked questions
Why do some retirees move back home after retiring abroad?
Usually not because of the country. The most common reasons are a lack of daily structure, loneliness after leaving long-time friends, and no clear sense of purpose once the novelty wears off. Planning your routine, social life and goals before you move solves most of it.
What should I do before retiring abroad?
Define your ideal normal day, build a weekly routine, plan where you will meet people and decide what you want to build or learn. Then test it with a one-week "retired at home" trial and a one or two month stay in your target country.
How do retirees make friends overseas?
Slowly, the same way as back home. Get comfortable with your own company, then stay open: join a sport or club, take a class, volunteer, and say yes to invitations from locals and other expats.
Is retiring abroad worth it?
For many people, yes. It can mean more adventure, more free time and a better lifestyle for less money. It works best when you move toward a life you have designed, not just away from one you are tired of.
How can I test retirement abroad before moving?
Spend one week living your planned retired routine at home, with no work and intentional structure, and note what breaks. Then do a one or two month trial stay overseas before selling anything or signing a long lease.
Keep planning
Want more on the mindset side? Watch Regrets You Can Avoid When Retiring Overseas and 10 Reasons You Should NOT Retire Abroad (Unless You're Ready).
Your Ideal Day?
What does your ideal normal day look like without work, and what's the biggest thing holding you back from living it? Tell me in the comments here or on YouTube. I read every one.
Subscribe on YouTubeI'm sharing my own experience, not financial, legal, tax or immigration advice. Costs, visa rules and services change, so confirm current details before you make big decisions.
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