How to Retire Young and Live Your Dream Life Overseas

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Happy Middle-Aged Couple /

Editor's Note: This story originally appeared on Live and Invest Overseas.

Go to school … get a job … work hard for a few decades … retire … then die.

For as long as I can remember, that’s the schedule we’ve been expected to adhere to.

Some people make it look good. I have friends now retiring in their early 60s with money in the bank, good health, and lots of time to spend doing whatever they want. Many retire to warmer climates like Florida or Arizona.

The first person I ever knew to retire and move to a foreign country was my nutty old grandfather. He moved to Mexico back in the late 1970s, never to be heard from again.

But those are variations on the same theme.

There Has to Be a Better Way

Worried woman at home thinking about retirement
Prostock-studio /

You don’t really get the freedom to enjoy life until the end. To me, waiting to die in paradise seems like such a sad place to end up.

There’s got to be a better way.

A little over 20 years ago, I discovered and joined a group of contrarian thinkers who have, for lack of a more original metaphor, taken the road less traveled. We retired in the middle of life and moved to another country.

Moving to Thailand Allows You to Retire Young

Hot springs in Thailand
Niwat panket /

Most of the people I’ve known for years in Thailand came here in their 40s with a little bit of money and completely changed the trajectory of their lives. Some started businesses here.

Some made income-producing investments. And more than a few are classically retired, playing golf, fishing, and chilling out under a palm tree.

Firstly, the big advantage of course is enjoying the freedom of retirement when you are 20 to 30 years younger than the typical retiree.

However, the downside is that the attrition rate is high with this lifestyle. People run out of money. Family issues pull them back. Every year I see a few old friends pack it up for home.

Those of us who have survived a couple of global economic crises, two coups, and a pandemic are good at adapting to new realities.

The Resilience of Thailand

ESB Professional /

Right now, people with money are doubling down by investing in small businesses and real estate here because they’ve witnessed the resilience of Thailand over and over again.

Out of necessity, some of us discovered ways to generate income working online. And as luck would have it, the post-pandemic global economy is offering up significantly more opportunities to “earn from anywhere” with a good internet connection.

After the pandemic, some brick-and-mortar companies discovered they function more efficiently with workers at home. Many adapted for the lockdowns and either didn’t switch back or became hybrids with a large part of their workforce operating remotely.

News outlets are reporting a rash of people quitting their nine-to-fives and chasing their dreams with new startups or freelancing. Freelance hiring sites are everywhere on the web. Go to job sites like LinkedIn, Glassdoor, or Indeed and scroll through the possibilities.

Years from now, when we are looking at the long-term effects of the COVID-19 pandemic, we’ll no doubt mark this as the time people woke up to the possibility of remote working on a global scale.

Expansion of the ‘Gig Economy’

Remote worker using a laptop outside in the sunshine
Alex Brylov /

What’s more, developing countries are waking up to the digital nomad phenomenon and changing their laws to attract remote workers.

Thailand, Cambodia, Vietnam, and Malaysia have all drafted new immigration laws and investment incentives to lure “high-net-worth individuals.”

The good news is that you don’t have to be rich or “high net worth” to take advantage of the new rules and incentives. Most importantly, all of these countries need to recover from the economic destruction of the pandemic, too.

Foreigners who come to live and inject their overseas money into the local economies are increasingly welcome.

This expansion of the “gig economy” paves the way for more retirees to change their plans. Instead of waiting around for Social Security, you could get a head start.

Find a Gig You Can Do From Anywhere

Happy senior on a laptop
Jacob Lund /

Do some research and find a gig you can do from anywhere.

At first, you might be discouraged because you don’t make enough to live in North America. But in a place like Thailand, Cambodia, or the Philippines, the cost of living is less than half.

In Anytown, USA, $2,000 a month will not buy a high standard of living. In Thailand, life is pretty good on two grand.

The gig economy has also been a godsend to traditional retirees where I live in Thailand who needed to supplement Social Security or whatever pension plan they may have.

And, as most people who have been retired for a while will confirm, you need something to do besides fish and golf.

Your Dream Life Overseas Every Day

A senior video chats on a laptop computer on his living room sofa
Roman Samborskyi /

Staying plugged into the planet and keeping your brain active helps you feel useful and relevant. The good thing about these gigs is that you don’t have to leave the house and nobody cares how old you are.

My neighbor is a 61-year-old American who took a TEFL (Teaching English as a Foreign Language) course seven years ago. He’s stayed busy and now teaches business English for corporations like Honda Motors, Nikon, and Kawasaki online from his kitchen table.

My 72-year-old friend from Kent, England, has a very posh and distinctive voice, so he found a gig making voiceovers for advertising and recording audiobooks online. He also has a sausage company.

How People Make It Work

Man on the phone looks at his computer
Evgeny Atamanenko /

My 50-something Irish friend who lives in Bangkok was in quite a fix when the pandemic came. He is a musician and normally plays six nights per week in different clubs. During the lockdowns, he started his own online piano school, teaching people of all ages how to play keyboards.

In addition, he also built a recording studio in his apartment and made several “spa” albums of music specifically for massage, yoga, and meditation … all sold online.

I have a photographer friend who sells her photos on a dozen stock photography websites.

I know a guy who teaches cooking classes on his YouTube channel while his wife works online as an HR administrator for a multinational corporation.

The fact is, every day when you wake up, there are more jobs available to do from anywhere than there were the day before.

Shift Your Work Mindset

Older woman working
Vane Nunes /

Normally, guys my age are complaining about technology and longing for the good old days, but the online gig economy phenomenon is a liberating development for people of all ages.

Certainly, we can start thinking about “work” as a thing that you do, not a place that you go.

Twenty years ago, my group of “retire-in-the-middlers” must have looked daft to buck the long-standing tradition of, “school … work … retire … die.” You can’t mess with the natural order of things.

The flaw in most of our plans was revealed when being separated from the homeland meant separation from income. If you ran into money trouble, you had to go home.

Nowadays, new businesses, new careers, and new lives spring to life every day out here in the metaverse. We look like pioneers who landed here before the internet revolution.

Retiring Young Without Being Rich Is Possible

Early retirees
Monkey Business Images /

Retiring young is possible without being rich … but we haven’t really rearranged the order of things. You still need to go to school. And that last step is inevitable.

In short, we’ve deleted the ugly “retire” part, and changed the definition of “work” to something that doesn’t interfere with our ability to enjoy what’s left of our “life.”

There’s more than one way to live life; retiring young now, more than ever.

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