Two Kinds of Expats: The Re-settler and the Nomad

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Some people move to a new country and set up an entirely new life: They’re in love with the culture, the people, and the new locales. These people are true re-settlers—They start up businesses, get their papers, and open local bank accounts in a whole other country.

But increasingly, there’s another kind of expat: the perpetual nomad. This is a person who works remotely and travels unrestricted. They may get paid online using services like PayPal or Venmo, and have several forms of side hustle, or use an all-online, international bank.

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Heather of Sea Bird Sailing Excursions is a re-settler: She discovered Costa Rica in 1999 and immediately knew she wanted to move here. Inspired in part by a Prince song (“Be glad that you are free. Free to change your mind. Free to go most anywhere, anytime“), Heather finally made the move in 2006 with just $13,000.

“I had never been scuba diving before but have always been an ocean girl…surfing, body boarding, body surfing,” Heather remembers. “I figured I could buy some PADI courses and become a professional diver.” After discovering that she would be making $400/month working for another tour company (what her rent was at the time), Heather decided to work for herself and start her own sailing tour business.

But the road to entrepreneurship was not without hiccups. To help protect herself and her investment, Heather obtained her Costa Rican residency quickly. Many expats find themselves doing ‘border runs’—That is, crossing the border every three months to renew the ‘tourist’ status.

“I realized that since I was going to be responsible for someone else’s 45′ yacht…I should start the residency process. I contacted Marcela Gurdian with Immigration Experts and we met one day for a coffee and she explained to me what needed to be done and how she could help.” Heather soon found that the immigration process was not always seamless. “It really helps to smile, say por favor and gracias…and be respectful even when totally frustrated! Anyway, I have permanent residency now and can easily renew the cedula with Banco de Costa Rica.”

“I feel much more secure being legal, having the CAJA insurance, even though I never use it…it’s there in case of emergency.”

Some pros to living in Costa Rica?

“Overall, living in Costa Rica and running a sailing tour business has been an awesome experience. I love this job and this country. People on vacation are always happy and the scenery while out on the water (and under water!) is such a joy to be around every day. I’m healthier here too since I eat more fruits and veggies and life is less stressful.”

What’s next? The business, which is highly rated on Trip Advisor, is now for sale! Could expat life in paradise be for you? Credit: Jennifer Dienst

Jennifer Dienst, who was born and raised in Florida, is the other kind of expat: the nomad. She is currently in Medellín and earns a living writing.

“I went freelance kind of by default,” Jennifer says. “I got laid off from my staff editor job and after a couple of years in PR and mulling law school, I was offered a few freelance writing/editing gigs that paid enough to support myself so I decided to make a go of it.”

After being laid off, Jennifer strongly considered a new career before going freelance. “Everyone kept telling me that the industry was dead and that I should find a new career. I’m glad I stuck it out, because they couldn’t have been more wrong. Yes, the industry has changed a lot and you need to be able to write for more than just print to be successful, but making a living as a freelance writer is definitely doable.”

Jennifer has been working freelance since 2012, but only went truly nomadic last year.

How many countries has she been to? About 25!

“I adored Myanmar; it was surreally beautiful and probably the best example of ‘exotic’ that I can think of. Spain, for its art and insane food scene. I’m in Colombia right now and I’m loving it. The landscape is stunning, I can’t get enough of it.”

Photo Credit: Jennifer Dienst

Jennifer, like Heather, recommends joining Facebook groups to find other expats. She also recommends finding a co-working space, because it’s easier to strike up a conversation than in a coffee house.

“Everyone wants to be a travel writer, so the market is super saturated,” Jennifer warns. “I write for consumer travel magazines sometimes, but my bread and butter is writing for travel trade publications, specifically about meeting and event planning. It’s a small niche but it pays well, the work is consistent, you get to go on press trips to cool places, but you’re not competing with 5,000 other freelancers to get the work.”

You can follow Jennifer’s journeys on www.! She is also a former participant in Remote Year, a program where remote workers travel with one another to all kinds of amazing corners of the globe (with wifi, of course).

What kind of expat are you? Would you want to re-settle, or endlessly roam, and where would you go?


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