8 Remote Workers On What It's Really Like to Work from Another Country

The pandemic gave millions of people who had never worked outside of an office building a taste of the digital nomad lifestyle. But what’s it like working remotely, by choice—it can’t be just posting sugar-coated Instagrams from far-flung destinations, right?

We put the call out through social media, and heard back from hundreds of remote workers—some who’ve only dipped a toe in the experience, and others who’ve been clocking in from a remote location for decades. Freedom, flexibility, and autonomy were their top lures; others were just happy to kill their commute. Many remote workers noted that they’re more productive now than they ever were in a traditional office setting; others missed QT with their cubemates.

As we sifted through everyone’s experiences, it quickly became evident that remote work is not without obstacles: Digital nomads bemoaned the lack of consistent Wi-Fi, juggling of time zones, anxieties about work performance, and myriad headaches of visas and taxes. But by and large, most were stoked to be working remotely, and hopeful for a future where jobs go to the best candidate—not just the best candidate in a particular place.

Here, eight digital nomads explain what it’s really like to work remotely, and share their best advice for others thinking about making the leap.

Rise to the challenge

Who: Erin Carey, 40, founder of the PR agency Roam Generation; plus her husband, Dave, and their three sons (ages 12, 10, and 7)

Work situation: The Careys work remotely from a 47-foot yacht—an idea inspired by Maidentrip, a documentary about the youngest woman ever to sail around the world. “We were not sailors, we had never owned a boat, and were not in the financial position to quit our government jobs and go out and buy a yacht,” Erin says. But two years and two months later, they figured it out—selling their home in Adelaide, Australia, flying to the Caribbean, and boarding a yacht they had bought sight unseen. The family of five cruised around for 18 months, then crossed the Atlantic to the Azores, where Erin launched her business. The family is still working and living afloat; the boat has a small workspace and Erin buys local SIM cards for hotspots.

Budget notes: Around $4,000 per month for the family, including fuel, food, marina bills, and land excursions.

The experience: “Living on a boat has allowed me to discover a new career that I love, meet inspiring people, make friends all over the world, and grow as a person,” she says. “I am more driven, persistent, and tenacious because this lifestyle demands it. It’s not easy living on a boat and traveling full time while running a PR agency, and being a Mum to three boys. Despite the boat’s constant breakages, homeschooling our kids, and living without a car, we would still choose this lifestyle time and time again.”

Her best advice: “Make a big, bold goal and then work backward. If you want to live in a bus and travel the U.S. or buy a boat and make that your floating office, make your decision non-negotiable and work toward it like failure is not an option,” Erin says. “Once you’ve made the decision to make something extraordinary happen, you’d be surprised how the universe conspires to make your dream a reality.”

When opportunity knocks, answer 

Who: Melany Rabideau, 28, the director of operational excellence for Adventist Healthcare; an assistant professor at the University of Global Health Equity in Rwanda; and a children’s book author

Work situation: Rabideau worked remotely from her home in Frederick, Maryland, for the first half of 2020. Though her job with Adventist was traditionally face forward, she was able to pivot online. “Migrating to a remote format because of COVID gave us a proof of concept that remote work can be just as—and even more effective—than in-person work,” says Rabideau, who earned her doctorate in organizational leadership in May 2020. This newfound ability to work remotely allowed her to accept a teaching position at the University of Global Health Equity in Kigali. Now Rabideau teaches leadership classes by day and leads project teams for Adventist at night—a schedule made possible by the time difference. “That sounds like a long day, but in comparison to the compounding costs of in-person work, the benefits of remote working are vast,” says Rabideau, who used to waste hours a day commuting to Washington, D.C. Now she has no commute, or even a car.

The experience: “Rwanda is a beautiful and safe place to live, work, and play,” says Rabideau, who has also worked remotely from Zanzibar, Namibia, and Ethiopia since August 2020. “A change of scenery is good for creativity,” she adds. “I find myself more engaged and thinking outside the box on projects because of my new perspective. Trivial things that may have frustrated me while I was working in the office don’t even fall on my radar now because my ‘office’—the whole wide world!—reminds you there is a bigger picture.”

Her best advice: “When things get tough remotely, we can go on mute, turn off our camera, and breathe,” she says. “This grace helps us sustain ourselves and improve work outputs.”

Carve out time for self-care

Who: Daniel Oppong, 33, founder of The Courage Collective, a diversity-, equity-, and inclusion-focused consulting company, and OhanaHealth, a platform designed to help early career candidates and high-growth health tech companies find each other

Work situation: Since spring of last year, Oppong has bounced to Nashville, Seattle, Washington, D.C., Dallas, and Miami, booking month-long stays through Landing, a collection of flexible-living apartments.

Budget notes: Pricing varies by city, but his range is $1,800 to $3,200 a month. “I want to feel what it’s really like to live in the ‘city proper,’” he says. “So I usually pay a premium to be near downtown or in one of the trendy neighborhoods.”

The experience: Oppong was already working remotely in Nashville for a Seattle-based tech company when he decided to start city hopping. He considers himself an “experience seeker,” and though COVID-19 slowed his roll, Landing made it possible for him to work from different cities throughout the pandemic. “The experience was limited, but I still enjoyed the novelty of being in a new place,” he says.

His best advice: “Create space in your day for non-work activities. This can be as simple as getting a workout in or going for a walk. In the world of remote work, it’s so easy to be sedentary. Your screen time is like 14 hours, 37 minutes, while your total steps are 17. Don’t do that to yourself.”

Keep your business above board

Who: Lauren Lancy, 41, fashion designer and product development consultant behind The Kindcraft, a digital magazine and shop featuring global designers and makers; plus her husband, Justin, a writer and technology consultant

Work situation: Lauren first started working remotely in 2010, freelancing for a trend forecasting group in London. From 2012 to 2018, she and Justin lived in Laos and Thailand. In 2014, they launched The Kindcraft. In 2018, they moved to Los Angeles, where they continue to work remotely for clients based around the world.

Budget notes: In Laos and Thailand, they stayed in short-term rentals or serviced apartments because they wanted “something that felt more like a real home base,” Lauren says. Signing a lease in Laos meant ponying up a year’s cash upfront, but there were other unexpected costs. “Getting and maintaining business visas was an ongoing expense,” she says. “Because our visa required us to leave the country and re-enter every 90 days, our travel costs ended up being substantial.” Even with that, their monthly budget was about a third of what they spent in the U.S.

The experience: “Getting paid and paying our vendors in multiple currencies was complicated, as was managing meetings and calls across multiple continents and time zones,” Lauren says. But it was through remote work that she developed such a robust network of international colleagues. After many designers and craftspeople were devastated by the halt of global tourism amid the pandemic, Lauren found herself in the gratifying position of being able to send them new business just when they needed it most.

Her best advice: Go through proper channels to secure your business visa. “Many remote workers we knew in Southeast Asia were flying under the radar on tourist visas,” Lauren says. “It was a risk, and occasionally we’d see people detained in immigration crack-downs.”

Be game for anything

Who: Dina Hill, 58, event planner

Work situation: Hill joined the Remote Year program in May 2017 and traveled to 12 cities in 10 countries while working remotely as a director of sales and events for a restaurant in New York. She was one of 50 people in her program, and at 54, the oldest—everyone else was in their 20s or 30s. When Hill tried to re-enter the traditional workforce a year later, she ran into some resistance during interviews. “Everyone thought I had been on a yearlong vacation,” she says. “Work then meant being in one location and overseen by management.” Hill eventually landed a job at a celebrity chef’s restaurant in Harlem but when COVID-19 hit, the restaurant closed and Hill was furloughed. She founded her own events company and moved to Columbus, Ohio, during the pandemic, but has since resumed her remote job with the restaurant.

Budget notes: The Remote Year program cost Hill about $2,000 per month, which included travel between countries, a workspace, an Airbnb-type home, three curated activities, and local city guides.

The experience: The program whisked Hill off to Croatia, Hungary, Portugal, Vietnam, Malaysia, Thailand, Argentina, Peru, Colombia, and Mexico, pairing her with a different roommate each month. “Having not lived with anyone since I divorced over 10 years ago, I learned about millennials,” says Hill, noting how much of Remote Year’s programming skewed younger. “I am an active person and was always able to participate, but there were many ‘bathing suit’ moments,” she says. “Being a woman in my 50s, I didn’t always feel comfortable.” That said, she opened up a lot during the trip. “I danced every night for the first 45 days,” she says. “It was like breaking free—I did not know how much I needed it.” 

Her best advice: “Be open.” That was the mantra that guided Hill throughout her remote work adventuring. She went on dates in foreign countries with the help of Google Translate, rode a donkey through terrifyingly steep coffee plantations in Colombia, and floated on a bamboo raft past elephants and snakes in Thailand. “Pushing my boundaries almost everyday was like living life on a high,” she says. “If I were to do it again, nothing would stop me from doing everything.”

Don’t get too attached

Who: Jamie Orsler, 32, a shipbroker for a London-based international shipping firm; plus his wife, Bonnie, and their three children (ages 4, 2, and 1)

Work situation: The Orslers arrived in the Cayman Islands in late 2020 via its Global Citizens Concierge Program, or GCCP, which grants two-year remote work visas to qualified applicants. They started out in a vacation rental, but have since moved to a complex with many families and communal amenities.

Budget notes: To qualify for the GCCP, applicants must make a minimum income of $150,000 USD annually if applying with an accompanying spouse or partner.

The experience: “It would be an absolute dream even without the backdrop that we are managing to escape a cold, masked, socially distanced society for a sunny climate without COVID,” says Jamie, noting how the Cayman Islands have been spared the worst of the pandemic thanks to strict entry and quarantine protocols. The kids are loving the change in environment, too: They’ve been snorkeling, swimming with stingrays, and making local friends. “The most challenging part is my hours,” says Jamie, who wakes up at 2 a.m. to work for his London office and goes to bed around 4 p.m. On weekends, he switches back to Cayman time so he can have some semblance of a social life. “Ultimately that means I’m jet lagged twice a week, every week, so Mondays can be a slog.” Adjusting to the limbo of semi-permanency is also a bit odd. “Two years is neither a lifetime nor a holiday, so we’ve had to adapt to that,” Jaime says. “We won’t be shipping our belongings over from the U.K., but we have kitted our house out with essentials for life—in our case, Barbies, black-out blinds, and other baby-related paraphernalia.”

His best advice: “Don’t fall in love with your new home too much,” warns Jamie, especially if “you need to be back in the office once the world opens up post-COVID.”

Make your workplace feel homey

Who: Geetika Agrawal, 42, founder of Vacation With An Artist, a creative travel experiences startup

Work situation: Agrawal left New York in 2015 to build her company while traveling with the Remote Year program. She worked from 12 countries in 12 months, and has continued to work remotely after returning to North America—in Mexico City, Los Angeles, Austin, and a “ dreamy” boat in Key West. Today she is back in New York but does not keep an office and continues to work with artists around the world. 

Budget notes: Agrawal slept in Airbnbs, hostels, and on friends’ couches, and worked from cafés and co-working spaces: all told, “a lot cheaper [than] living in New York.”

The experience: “I found myself more open to taking risks and pursuing unconventional ideas [in my work],” says Agrawal, who loved the freedom of working anywhere, meeting new people, and dumping what she calls “the mental burden of stuff.”

Her best advice: Stay in each place for at least a month and do little things to make it cozier. “I used to get flowers and groceries on my first day to make it feel like home,” says Agrawal, who also carried staple spices and a pot so she could cook her own meals. “If you’re going to be on the road for long, you want to create habits that will sustain you.”

Find yourself a community

Who: Rachel Coleman, 28, independent education consultant and co-founder of College Essay Editor, and her life and business partner Stazi Gueordjev

Work situation: Coleman left the U.S. Senate in spring of 2015 to work for herself. She has been location-independent for more than six years, working remotely from Bulgaria, Georgia, Uzbekistan, Cyprus, and Italy.

Budget notes: To keep their spending under $10,000 a year in the beginning, Coleman and Gueordjev house sat via Trusted House Sitters. Today they rent long-term Airbnbs and work from cafes with an annual budget of $20,000 to $25,000.

The experience: “What I love most is the freedom and autonomy I have to direct my life and my business,” Coleman says. “This demands more responsibility and self-determination, but I’m rewarded by the satisfaction of taking ownership of my work and destiny.” More importantly, remote work has given Coleman an opportunity to immerse herself in new places and ideas, confirming for her “just how similar humans are across cultures, social classes, or even religious communities.” One challenge worth highlighting, she says, is the absence of a work community and office friendships that can make a person feel isolated. “I am fortunate that I have a partner who works from home with me, so I am never on my own, but it was an adjustment to realize that if I wanted a sustained community outside of my family and my partner, I needed to create it myself,” she says. Like any self-starter, she devised a strategy and implemented it—participating in book clubs with friends from high school and college, joining local expat and remote work communities, and attending festivals, lectures, and English-language pub quizzes wherever they’re based at the moment.

Her best advice: “Saving, limiting excessive spending, and working towards paying off any debt will give you more freedom and room for error,” Coleman says. “It’s also important to remember that working remotely is not a vacation. There will still be stressful work days and frustrating setbacks, whether you’re on a beach in Italy or in an office building in New York. So go into this new career path eyes wide open, acknowledging that you’re not eliminating your work, merely changing its venue.”

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