It’s Never Been Easier To Freelance From Abroad

by Emily Wenstrom

Freelancing has always been associated with freedom: from desks, from bosses, from suits. But it’s not just offices from which freelancers and other remote workers are escaping anymore. Many are hightailing it to other continents. As the trend grows, new organizations are coming up with ways to make it more convenient and social.

The freelancing expatriate is nothing new. Instead of waiting to earn his or her two weeks of vacation to tour Italy, the traveling freelancer prefers to simply live there for a few months. As long as s/he can keep up with clients and deadlines, why not? Technology has only enhanced the freedoms that freelancing can offer, and these days any place with an Internet connection can be a workspace, whether it’s in New York or Thailand.

Take, for example, Shannon O’Donnell, a 2013 National Geographic Traveler of the Year. She’s been living almost completely in other countries, making only occasional pit-stops in her home state of Florida to visit with family, for seven years now, with no plans to stop any time soon.

“I still work a lot,” O’Donnell said. “But instead of going home and watching Netflix on the weekend, I meet up for drinks with other travelers, or I hike up a mountain.”

At the time of this interview, O’Donnell was housesitting in London for a month, and about to head off on a long weekend in Denmark. Professionally, O’Donnell is a freelance writer and marketing consultant. She also runs the travel blog A Little Adrift, as well as Grassroots Volunteering, which helps other travelers identify ways to give back and spent responsibly while they travel.

O’Donnell said traveling while working is rewarding, the logistics of the lifestyle can get complicated quickly. Freelancers who want to travel long-term should be wary of needs like visas and always research extensively before going somewhere new.

However, new organizations are cropping up that can simplify the planning stage so that remote workers can focus on their business and travel experiences.

For example, Hacker Paradise sets up a coworking space in a new location every few months, and invites remote workers to join them there for periods ranging from a couple weeks to a month or more. Within a community of like-minded freelancers, participants are free to pursue personally set career goals and enjoy exploring a new culture.

Another, Remote Year, takes a group of remote workers to twelve cities all over the world over a span of 12 months. Each traveler is responsible for their own work, but Remote Year coordinates shared workspaces, living spaces and some meals for each destination over the year. The first group started its journey last June and have already spent time in Prague, Czech Republic; Lubljana, Slovenia; Cavtat, Croatia; and Istanbul, Turkey.

These opportunities come with some real perks compared to traveling solo. To start, international travel can feel less intimidating when with a group. It can lead to lifelong friendships. And it’s always nice to know for sure where your next bed will be, and that you’re sure to have the Internet connection you need to deliver that next project.

But these perks will cost you. A slot in the Remote Year program costs $2,000 a month. Paradise Hacker varies widely depending on the duration of the trip and the destination. And even with these groups, freelancers are on their own to secure their paychecks.

Is the tradeoff worth it? It may come down to temperament.

While O’Donnell enjoys her independent life, she said, “I like the idea of a community. Not everyone is cut out for solo travel.”

Research and planning are absolutely critical for a solo traveler, and O’Donnell recommends using travel blogs to research new destinations before buying a ticket. Furthermore, solo travelers need to be even more internally motivated and disciplined than the average freelancer. Just imagine pushing off a project until deadline, only to have a monsoon wipe out all power in the region and cut off the wifi.

Traveling with an organized group like Remote Year can drastically cut down on these wild card moments, lending more structure and socialization to a freelancer’s travels. But doing so also leaves less room for improvisation and independence.

All in all, technology means there’s less reason than ever to stay tied to a cubicle, or even plugged into a wall, to earn a living. But taking your life and work overseas comes with a whole new set of challenges. For those who want to explore the world but aren’t ready to leave all connections and stability behind, organizations like Remote Year and Hacker Paradise can bridge the gap.

Emily Wenstrom writes about pop culture, creative writing and lifestyle topics; she also advises clients in content strategy.

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