
A simple Google search will show that there are hundreds of websites and other resources devoted to telling you how much money you need to retire in exotic places all over the world. There are many other sites that will tell you what the requirements are for visas, health insurance, licenses and other essentials necessary to retire overseas.
Since I have created an easily transportable, minimalist lifestyle for my retirement I often read these sites with intense interest. But, before you figure out how to retire abroad, maybe you should figure out if you should retire abroad.
See also:
- 4 Things I Wish I’d Known Before Retiring Abroad
- Life is Either a Daring Adventure or Nothing
- Where is Home?
- Taking a Leap of Faith
- The Things You Own End Up Owning You Essay
- Essentials Required for Retiring Overseas
- Why No-one Cares About Your Travels
- Non Financial Tricks For A Happy Retirement
- When Enough Is Enough
- The Good Enough Retirement
- Happy Retirement Wishes
Financial websites will help with planning and investment, but what these sites neglect to tell you are things that are more basic than savings, insurance, logistics, and paperwork.
These are essentials of a more personal nature but are required if you are going to have a successful life as a retired expat. Bear in mind, there are as many kinds of expats as there are people living abroad, but the most successful of them tend to have some common traits.
Desire to Live Overseas
You can’t be just “interested” in moving abroad if you want to thrive in your new life. Just because you traveled here and there on vacation while you were working and found it pleasant, doesn’t mean you should pack up and move your life overseas. To be highly successful you have to go beyond being interested and have a deeply passionate desire to live in new places and experience new things.
Without that desire small items, that may, in reality, be only a minor inconvenience, will seem like huge obstacles that sap your energy and drag you down. Without a passion for living a life “contrary to ordinary,” you are setting yourself up for failure.
Attitude About Living Abroad
When retiring abroad there is more to consider than what it costs and paperwork.
If you think the world is a place to be feared and people are generally filled with bad intent, you should probably reevaluate your plans to live overseas. In truth, the vast majority of people in the world are tolerant, welcoming and generous, but you wouldn’t know that from the stereotypes perpetuated in the news.
You can’t be happy if you are afraid of your surroundings or if the thought of what lies around the next corner fills you with dread. Instead of looking only at what is in the headlines, dig deeper and look at actual information. You may find the place you have been considering is safer than home.
Flexibility
You need to be flexible and know that just because things are different than what you are used to, it doesn’t make them wrong. When I lived in Thailand I paid my electric and phone bills, like everyone else, at 7/11.
In Mexico, appointments were generally more like suggestions that a meeting might take place. In Vietnam, the best coffee is served street side on tiny blue stools.
In Myanmar, you call the waiter by making “kissy” sounds. Driving may seem chaotic and in some places, the simple act of going to the toilet can seem “foreign”. These and thousands of other things are something you just need to learn to accept.

The Ability to Let Go of Your Stuff
Buddhists say that attachment is one of the greatest causes of human misery. Generally moving overseas means giving up, or at least being apart from, your things. If you need the reassurance of being surrounded by a house full of your own possessions, you are going to have to come to terms with that. If you were looking merely to replicate your old life in a new location, you might as well stay home.
The Ability to Let Go of Your Opinions
Attachment can even extend to our attitudes and mindset. Even in light of new evidence, humans have a tendency to remain attached to old opinions. A life of travel can (and should) challenge everything you believe in.
If your opinions cannot be supported by new information you may have to adjust. If they do withstand new information they will be strengthened. Failure to change opinions in light of new facts will only result in alienation and frustration in your new home.
The Ability to Operate Outside of Your Comfort Zones
The very act of living overseas can be challenging and sometimes it pushes us to our limits.
There is a saying that, “The magic in life takes place at the edges of our comfort zones.” The very act of living overseas can be challenging and sometimes it pushes us to our limits. And isn’t that actually the point? How can we ever know how far we can go if we don’t get near to, and occasionally cross, the boundaries of what we find comfortable?
Trying new things, going further, taking calculated risks and occasionally throwing caution to the wind is a great way to expand your horizons, or at the very least, a way to help you better appreciate what you have when you get back to your comfortable place.
Curiosity About the World
Being interested in learning about a new place and the culture of your new home is essential in thriving as an expat. You will encounter new traditions, new taboos and new ways of thinking. It is possible to relocate overseas and operate almost exclusively inside expatriate bubbles, but if you want to truly thrive in your new locale you need to find out how it works and what makes it tick.

Retiring Abroad is Not About Running Away
The most successful overseas retirees are those that are running toward something, not running away. If you want to move overseas because you are miserable at home, you are more than likely just going to bring your misery with you. A person that hates everything back home will likely hate everything overseas as well.
A new setting in and of itself does not magically transform a person. However, if you are willing and open to change, travel can be a great catalyst. If your expectations are realistic, your heart open and your curiosity unquenchable; you are probably a good candidate for living an extraordinary life overseas.
Hi Johathan
From the same guy who wrote back to you about the Cobra eating thing. Just wanted to say that I really enjoyed reading and absorbing this article. It makes 100% sense. Getting rid of my STUFF was the best thing that happened to me and it wasn’t what I was looking for at the time, but I’m glad it did as I realized there were much bigger and better things out there than ordinary. Long time travel is not for everyone, but for me, it’s all about learning and appreciating everything life has to offer.
gadabout grahame
Thanks Grahame,
A lot of people think they want it, but many don’t know the sacrifices necessary. First of all you have to know yourself. It is absolutely an amazing life and I can’t imagine trading it for anything else.
It’s always a mystery to me why some people drag a shipping container full of their stuff to some third world area where they haven’t even tested the waters yet. The monetary value of their stuff may not even equal the shipping costs.
Even at the age of 62, I’m still traveling with what I can put in one large backpack and another for my wife. When my wife and I do settle down (who knows when or where or for what length of time), we’ll probably add another backpack’s worth of stuff.
I began 10 years ago without a definite end date, and still do not have one. The main thing that we miss is not living with a German Shepherd dog again. At least that is one thing we’re saving for the future.
Tippaya and Mark
Tippaya and Mark,
I totally agree. I get frustrated if I need more than two small bags when I am traveling. I know some people want to live like they do at home when they are on the road, but I don’t really get the point of that.
Hello Mr. Look,
Not sure where or when I’ve met you but I do remember we had a good chat over the beer.
With a name card I have received grom you, finally got a chance to check your web site.
You are telling the story that reside within me and I thank you for that.
Well written Jonathan, strong sense of adventure required, and of course a good sense of humour never goes amiss when things don’t quite work out as planned !
Thanks Ben. I see so many articles written about the financial and technical immigration aspects of what it takes to retire overseas. I thought it was time to address the most important issues.
Nice article
How do you go about securing insurance coverage .
I have followed your adventures since your start.
Enjoy
Thanks Walter. I am lucky, I have insurance from my old job. What I have found is that most people moving here to Portugal get private local insurance for about 60 Euros a month. I am not sure what that covers, requirements, or how it would interfere with US coverage, but no one seems to worry and remarkably, not many seem to complain. One thing I would suggest is joining some of the expat forums on Facebook (Americans in Portugal, Expats in Portugal) and seeing what works for different people. I should write a piece on it, but the information changes often and varies according to circumstances.