An Expert Guide to Traveling the World as a Digital Nomad

Once a crazy pipe dream for wanderlusters, the idea that you can earn a living while traveling has now become a full-blown, attainable reality. In an increasingly connected world, more and more individuals—especially those in the creative and tech sectors, like freelance writers, web developers, and digital marketers—are taking advantage of the opportunities for remote work. Some members of the burgeoning community even predict that we could reach an incredible 1 billion of these “digital nomads” by 2035.

The interest is so strong that an entire industry has sprung up in response: Programs like Remote Year and Hacker Paradise, much like traditional tour operators, facilitate the travel logistics for groups of digital nomads who travel together to different countries, but these trips last anywhere from three months to a year or more. Coworking brands like WeWork and Copass give professionals access to office-like work spaces around the world. Even hotels are accommodating this new type of traveler. Selina, an international digital nomad hotel brand, offers accommodations, a coworking space, and other amenities like yoga and surfing classes. The brand, which currently has locations across Central and South America, is opening its first U.S. outpost in Miami in September and plans to expand across the country by the end of 2019.

But while these new brands make it easier than ever to work and travel, that doesn’t mean it’s now a total piece of cake. Working on the road comes with all sorts of challenges like coordinating meetings in different time zones, maintaining a healthy lifestyle when you’re constantly on the move, coping with travel burnout, and dealing with guilt and FOMO—“fear of missing out”—when you’re stuck on your laptop instead of exploring your new surroundings.

As an NYC-based freelance travel writer, these are obstacles I know all too well. That’s why I checked in with a range of professional remote workers—from full-time digital nomads to people who simply travel often for their jobs—to find out how they actually pull it off. The result? An expert guide to working and traveling at the same time, sourced from people who’ve mastered the art.

First, create a daily routine—even if it’s for a brief period of time

Greg Caplan, the founder of Remote Year, says that whenever he arrives in a new place, he always does the same thing: Head to the closest convenience store and buy a carton of eggs and two bottles of red wine. “It’s a small thing,” he explains, “but it’s nice to know that wherever I am in the world, I’ll have a glass of red wine before bed and some eggs in the morning.” Not surprisingly, Caplan’s company was founded on the idea of maintaining routine: “We want to help our participants keep a consistent lifestyle wherever possible so that they can enjoy variety elsewhere—in the local activities and events,” he explains. Creating a daily routine can make it easier to finish your work and then allow you to explore your new surroundings without guilt or stress.

That’s certainly been the case for 29-year-old Duncan Falk, a full-time digital nomad who traveled with Remote Year last year and has been working from Selina’s space in Medellin, Colombia, for the past six months. Falk lives in an apartment in Medellin and commutes to Selina, takes a lunch break, and at the end of the day, tries to have as normal a night as possible—maybe adding on a happy hour or a walk in a new neighborhood. “It feels more like home this way,” he explains. “When you’re at home, you can’t play every day or just work for two hours and expect to afford your life. Same goes for when you’re on the road: You do your daily routine, but then after work, you get to explore a new place.”

Creating a routine can also help you avoid burnout. I always try to maintain some semblance of my morning wellness and beauty routines while traveling. As a morning runner, I try to hit the pavement first thing when I wake up, no matter where I am. There are physical benefits, yes—staying healthy allows me to endure long journeys or travel mishaps—but it’s also mental. My well-being is less likely to be thrown out of whack if I stick to my routines, like my very specific morning skincare ritual. It may sound trivial, but doing the same thing every morning no matter where I am helps me feel more grounded and stable, which in turn makes for more sustainable long-term travel.

Courtesy of Remote Year

Coworking spaces don’t just provide reliable internet—they’re also great places to make other types of connections.

Make new friends—work buddies are digital nomad gold

That’s a tip Michelle Lawson, cofounder of The Remote Experience and a digital nomad herself, understands all too well. “Misery loves company, and I’ve found that working with someone who is also missing out on the same travel activities you want to do really helps manage FOMO,” the 27-year-old explains. Once, when Lawson was leading a group through Asia, several participants were working East Coast hours. “They’d all huddle together in the villas at 3 a.m., taking meetings and working together,” she remembers. “No one wants to be on call in the middle of the night, but they all motivated each other, which really helped.”

Traveling with buddies can even help you create and maintain a routine. “Our participants often go to the gym together in one big group, and then walk to the coworking space after their workout,” says Dale Johnson, 28, chief marketing officer of Hacker Paradise and a veteran digital nomad himself. “The camaraderie of it is so real—it’s a lot easier for many people to get motivated in a group than on their own.”

Embrace the digital experience with all the useful technological tools out there

“If you’re traveling on a regular basis, it’s key to have all your files accessible in the cloud, so you’re essentially [working at] a virtual desk,” advises Michael Hoevel, a U.K.-based 38-year-old managing director of a communications agency; he travels for work four to five months out of the year. Once you’re organized, check out some other tools digital nomads love:

• The Google Fi phone plan replaces a standard cell phone carrier. It picks up cell signals from partner carriers around the world, so your phone will work in over 170 countries. Your clients won’t even know you’re abroad. It only qualifies with a few phones (mostly the Google Phone), but you can also activate a sim card for an iPhone.
• Mobile wireless hot spots let you access the internet from your phone without Wi-Fi—and without using data. “I [can] answer emails in the back of Lyfts, right until my flight is about to take off, and while grabbing a coffee—without having to ask about Wi-Fi codes or rely on crowded networks,” says Christine Amorose Merrill, an ad sales manager who travels frequently and runs the travel blog C’est Christine. “Knowing that I can get on the internet anywhere—not just when I find a place with Wi-Fi—makes it a lot less stressful to work on the road.”  
• World Time Buddy is a web and mobile app that shows four or five time zones at a time, so you don’t have to calculate differences yourself.
• Zoom, a video conferencing platform, is great for video calls. “Video creates a much stronger connection with your clients. You get more intimacy than [you do] sitting in a conference room, because you see their full face and their full experience,” says Caplan.

Join the growing digital community of fellow nomads

“It’s cool to have an online community of people around the world,” says Falk. “I’ll go on [these sites] every so often, and everyone’s always talking about useful stuff, like, ‘Oh, what kind of suitcase should I bring for this trip?’ or ‘I’m in Guatemala, anyone else here right now?’” Here are a few resources that will put you in touch with this online world:

• WorkFrom.co is a crowdsourced resource that lists all of the good places (coffee shops, hotels, etc.) that you can work from wherever you are. It’s updated in real time, too, so it won’t steer you wrong.
• NomadList ranks the best cities for digital nomads based on metrics like Wi-Fi speed and currency exchange rates.
• With digital nomad community forums, like the Slack channel on the WorkFrom.co website and the digital community on NomadList, you can talk to fellow nomads whenever you want, wherever you want.

When travel FOMO looms and you can’t seem to get “remote-ivated” to work, try this mind trick

It’s a tactic Falk absolutely swears by: “Instead of thinking of work as something I have to do, I think of it as something that has created this opportunity for me to travel,” he explains. “I remind myself that my work allows me to be in this new destination in the first place—and that small mental shift makes it easier to concentrate on getting the work done so I can explore after.” Which, of course, is the whole point.

>>Next: These Countries Just Made It Easier for Americans to Move and Work Abroad