Surprise! Live Abroad and See MORE of Family and Friends

You’ve got to be kidding! You’re paying how much for this?

My cousin Eryn was flabbergasted by the gorgeous penthouse I’d rented in St Julian’s, Malta, overlooking Spinola Bay. It was 2013, and housing was so cheap I’d be able to rent it for three months.

The idea was to invite guests to assuage the loneliness that came and went while I was slow-traveling the globe.

Eryn and her husband had come from London, and we spent the week exploring the island, stopping at abandoned beaches and ruins older than the pyramids. We took a ferry to the neighboring island of Gozo, and ate as much pizza and pasta as our stomachs could hold.

As they were leaving for the airport, however, I felt a pang of sadness: I would be spending Christmas in Malta alone.

They saw the look on my face. “Come to England!” they chimed. So, I did.

A Family-Oriented Resolution

The beauty of a jetsetting lifestyle: You can adjust your travel plans, intersecting with family when—and where—you can.

I booked my flight from Malta to London on a whim. I never would have been able to do so from the US, given the cost of flights there. But fares from Valletta to London Gatwick run as low as €16 ($17) one-way on easyJet… a price that allowed for a last-minute holiday trip.

In London, we cooked dinners, brewed mulled wine, and shopped at Oxford Street and Covent Garden. The holidays, I learned, are a special time in England. Streets and outdoor markets, like Covent Garden’s Apple Market, are draped in Christmas lights.

But the highlight of my trip to England was Devon, where my cousin’s husband’s family is from. I had a true British holiday: watching the Queen’s Address, indulging in a Christmas roast, and munching plenty of sweets—from decadent sticky toffee pudding to a sponge cake drenched in warm toffee syrup.

And I discovered Boxing Day: Great Britain’s answer to Black Friday.

I never would have discovered these traditions if I’d stayed alone in my penthouse.

I made a New Year’s resolution to call on friends when I’m lonely.

Bring the World to Your Family

Two years ago, I spent Thanksgiving with my cousins in Austin, Texas. Before that, I made a trek to Michigan to visit relatives I’d never met before, including my Sicilian grandmother’s older sister, who greeted me with a photo of my grandma as a baby.

It might be counterintuitive, but globetrotting has afforded me more quality time with friends and family than if I had a US-based job, with two weeks of annual vacation and a fixed home address.

My siblings have visited me during my stays in Costa Rica and Nicaragua. For my brother, each visit doubled as a surf trip and a tax write-off, since he’s a professional surf photographer. While my sister was in college, she visited me during her summer vacation, and even interned for me at my real estate office in Nicaragua.

Working remotely, living as an expat, or being a roving retiree can allow you to spend consecutive weeks near family, because of your location flexibility and the savings that come with living abroad.

Since I moved overseas twenty years ago, I spend at least two months with my parents each year. I spend four to six weeks at their Florida home, and one to two weeks traveling with them. I’ve inspired my parents to become jetsetters; after 50 years without a passport, my dad finally applied for his to visit me. Now, he goes to Mexico to swim with whale sharks, joins friends on sailing trips in the Virgin Islands, and road trips Europe with my mom each year. Meanwhile, my mom and I have been to at least 10 countries together, from Costa Rica to Italy to Austria.

I cherish sharing my overseas lifestyle with my parents as we make new, untraditional memories together. And involving them has made them more comfortable with me traveling the world—often alone.

It’s Easier Than Ever to Stay Connected

Matt Bowles, founder of Maverick Investor Group and Maverick Show Podcast, has been location-independent for ten years. He spends a month each year in the US, calculating his days to qualify for the Foreign Earned Income Exclusion (FEIE), a tax deduction for overseas U.S. citizens.

Matt travels for the other eleven months per year, and has 80 countries under his belt. He’s the “cool uncle,” bringing gifts like a soccer jersey from Ghana to his nieces and nephews.

“My number one priority is spending quality time with my family in the United States,” he says. “That’s the value of location independence: I get to choose. With a regular job, you can’t normally take a month off work to see family.”

Living overseas, he says, allows him to select the best times of year to travel home for a visit… while providing a destination for family members to visit him on holiday.

Natalia Turnbull, a member of my Facebook Group, Badass Digital Nomads, gave her 81-year-old mother an iPhone before leaving for global travel. “With video chats, my mom has had more contact with me since I left than when I lived in the same city for 52 years,” she says.

Ted Parsons, also in the group, chimed in. “I learned during COVID that you can retain friends even when you can’t see them,” he says. “It’s helped me realize that having friends doesn’t change with proximity. I wish all my friends were traveling with me, but that’s just reality.”

Longtime IL editors Suzan Haskins and Dan Prescher, too, have discovered that living overseas has improved their family life.

After becoming empty nesters in the early 2000s, the couple left their home and careers in Nebraska for San Miguel de Allende, Mexico. Their son Brandon, then a college student, spent a few months with them to study Spanish… and he became enamored with the expat lifestyle, too. He made the leap to Panama, where he met his now-wife.

“Our family is what it is today because of our expat experience,” explains Suzan. “If we hadn’t moved overseas—if our son hadn’t followed—we wouldn’t have our Panama family, our daughter-in-law, or our sweet Panamanian granddaughter.”

The whole family’s currently back in the States while Suzan cares for aging family members.

She and Dan live only a few blocks away from their son’s family, but she admits, “The years when we lived overseas and returned for a visit were better bonding time. We stayed with our kids and knew we had limited time together, so we made sure it was quality time.

“Today, we can go a week or more without seeing one another, and then it’s just dinner or a school or sports activity.”

The couple plans to move back to Mexico in the future, and they’ve already bought a condo in Cabo, thanks to Ronan McMahon’s RETA deals (see our inaugural International Real Estate Index in this issue).

As Suzan says, “We know wherever we go, our family will come visit us… especially if it’s on the beach in Mexico.”