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Chucking It All at 50 to Retire Around the World

3 years after shedding his possessions, he says he's living richly

By Jonathan Look

Three years ago, I was living the prototypical American Dream — a home in a gated community, new cars in the driveway and a country club membership. I was making good money as an air traffic controller, but spending it on stuff I didn’t need. Stuck in a consumerist rut, I’d become what Henry David Thoreau called, “the tools of my tools.”

My 50 birthday and an opportunity to take early retirement were rapidly approaching, so I decided to ask myself some questions:

  • If I was happiest traveling, writing, taking photographs, making friends and having adventures, why was I spending my life sequestered at work and in the comfortable but boring bubble I’d created for myself?
  • Why did I keep accumulating possessions that drained my finances, tied me down and consumed what little spare time I had?
  • Could I reprioritize my life in way that would let me take early retirement and do the things that made me happiest?

His Plan: The Vagabond Life

After some soul searching, I decided to sell almost all of my stuff (house included) and travel the world — one country at a time, one year at a time — working occasionally as a photographer, writer and teacher and doing volunteer work. I'd be a vagabond and I’d do it for 10 years.

(MORE: How to Retire All Over the World)

Spending a year in one place, I figured, would allow me to start learning the culture, see the seasons and make some real relationships. I could take advantage of long-term rentals, learn how to live like the locals and have some time for relaxation to boot.

Paring my possessions down to a minimum would provide flexibility of movement and help me find out what I really needed to enjoy life. I wanted to — indeed I longed to —push my boundaries and quit playing it safe.

What His Friends Thought

Most of my friends thought I was crazy to give up everything and travel the world. Some seemed to think I’d be betraying the consumerist ethic that says the goal of life is to accumulate more and more “stuff” until you die. Others thought I was going through a midlife crisis and would be back in a few months longing for the return of what I’d shed. A few believed I had the germ of a good idea and was on the right track, but that my plan was unworkable.

(MORE: Best Places to Retire Abroad in 2015)

It’s now been three years since I actually began doing it. While I haven’t strictly adhered to my original “base one place for one year” idea, I have lived in, and certainly traveled in, some amazing places.

How His Plan Has Worked Out

I started with five months on the beach in Xcalak, a tiny village on the Caribbean coast of Mexico, and then spent seven months high in the mountains of southern Mexico in the town of San Cristobal de las Casas.


Next, I followed a few months back in the United States with nine months in the shadow of Angkor Wat in the Cambodian town of Siem Reap. For the past 18 months or so, I’ve been based in Chiang Mai, Thailand. In the interim, I spent a month in Bali, a month in Myanmar (Burma) and a month in Laos. I’ve also traveled to Bhutan, Canada, Chile, China, Guatemala, Malaysia, Peru and Vietnam.

(MORE: Best and Worst Reasons to Retire Early)

Right now, I’m in the process of discarding what little dross I’ve accumulated in Thailand for a move further afield in Southeast Asia.

Not Rich, But Living Richly

After three years, I am not rich, but I am living more richly than ever before.

I can hardly believe the places I have seen and the adventures I’ve had since retirement.  I know that from the outside it must all seem expensive and extravagant, but it really isn’t. All it has required is a recalibration of the things that I value and see as important.

My base living expenses are less than 20 percent of what they were back in the states when I was looking for meaning in the things I bought and consumed.

Now, instead of finding ways to kill time, I spend my days running toward life and living life consciously and deliberately.

Over the last few years I have seen a lot of places and learned a lot about myself, but the biggest thing I have discovered is that retirement can be a time of reinvention and living your dreams.

Retirement should be simply a new phase of life or truly, Life Part 2.
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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