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4 Things I Wish I'd Known Before Retiring Abroad

He began retiring all over the world at 50, in 2012

By Jonathan Look

Living your retirement abroad can be an immensely rewarding experience. I know; I’ve been doing it since I left my U.S. home, at 50, three years ago to begin my early retirement traveling around the world. But there are four things to keep in mind before you make the leap (I wish I’d known them before I started out):
No. 1: Retiring Overseas Isn't a Vacation
After you’ve packed up your life, said goodbye to your friends and moved to your new exotic overseas home, there will soon come that moment when you realize: This is not a vacation, this is my life.

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There are bills to be paid and chores to be dealt with. Finding the best markets and restaurants, making new friends and learning the ropes in your new location is fun, but eventually you’re going to need to find something more.
Many people plan for their financial needs in retirement, but they neglect the psychological and emotional aspects. That’s a big mistake. You don’t want to spend the best years of your life just frittering your time away. Although it may seem so at first, living abroad is not in itself an actual activity.
So before you start out, come up with a project (or many) and prepare to do things you’ll find rewarding. If you haven’t discovered your passions, this is the perfect time to find them. If you already know your passions, this is a perfect time to delve into them further.
No. 2: Comfort and Happiness Aren’t the Same
One of the things I used to hear over and over from people like me nearing retirement age was that they just wanted to be comfortable in retirement. Mostly they were referring to their finances, but often they were also talking about creating a sort of secure cocoon somewhere where they could hide from their worries, too. Problem is, as I’ve since learned, comfort and happiness aren’t the same thing.

(MORE: Chucking It All to Retire Around the World)
As people get older, they tend to start playing it safe while sacrificing their happiness. To me, there would be nothing sadder than to move somewhere and be seduced into a life with plenty of comfort, but little happiness. Wouldn’t it be better to use retirement abroad as an opportunity to push our comfort zones and find out new things about the world and ourselves?
No. 3: No Place Is Perfect
As I’ve been traveling the world in retirement, I’ve discovered that it’s truly an amazing place, but if you go looking for perfection you’re going to be disappointed.
Every place has periods of bad weather, dodgy parts of town and potholes. Bureaucracies and inefficiencies exist everywhere (albeit, more in some places than others). If you let them, they can be doubly frustrating when you don’t know the culture.

(MORE: Obstacles to Retiring Abroad)
How you deal with the negative aspects of any place comes down to a choice: They can be a trying ordeal or a challenging adventure.
In my experience, people who thrive abroad are the ones who are mentally prepared for dealing with things that are less than perfect.
Paradise is an attitude as much as it is a place.
No. 4: The World Isn’t That Scary After All
Before I headed out on my new adventure, I was a little fearful of what I might find in some exotic locations. But I can now report that in spite of the way things are presented in the 24-hour news cycle, the world isn’t that dangerous or scary.
So before you write off a place based on the latest event or news headline, do your homework. It’s entirely possible that hyped-up events in the news might keep you from going to a place that is safer than where you are now.
Fear is a phenomenon that is largely media-driven and marketing-created. I can’t begin to tell you how many people I’ve met overseas who, after watching their own country’s news channels, say they’d be afraid to go to into a movie theater or a school in the United States. We know doing those things are safe, but media exploitation can make some foreigners think otherwise.
Here’s the most important thing I’ve learned retiring abroad: There are far more places to live overseas filled with wonderful people who will generously accept you into their community than there are places where people wish you harm.
English is spoken widely and no matter how far afield you travel, chances are there will be someone with at least a basic knowledge of it. Knowing how to say “hello,” “please” and “thank you” in the local lingo will get you started. Having a great attitude and a genuine smile while you’re learning the native language will get you even further.
Jonathan Look, a photographer and writer, lives by the philosophy: “Why sip life from a straw when you can drink it from a fire hose?” You can sign up for his newsletter here, visit his website at or visit him on Facebook.

Jonathan Look At age 50, Jonathan Look Jr., sold everything he owned, took early retirement and began exploring the world. He believed the best of life comes from being true to yourself and pushing against the edges of your comfort zone. Unfortunately, Jonathan passed away in March of 2021. He shared his unique philosophy and stories of his adventures on his website, Read More
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