Does Working Remotely Really Work?

Casey Hynes

When I tell people I lived abroad for nearly five years, one of the first questions they ask is, “What did you do while you were there?” People aren’t asking about my killer travel stories of cuddling a baby tiger or raving on a Chinese naval carrier, either. They want to know how I earned a living.

I moved to Seoul, South Korea in 2010 to teach English. When I relocated to Beijing for another teaching job a year later, I realized I missed my former profession, journalism. So I stayed in Beijing and pursued my lifelong dream of becoming a freelance writer, contributing to a variety of international publications and supplementing my income with editing and copywriting work. During that time, I traveled throughout Asia and lived in China and Chiang Mai (a city in Northern Thailand), all while working for a variety of clients, many of them U.S.-based.

And I’m not the only one. A growing number of people are opting for location-independent lifestyles as so-called “digital nomads,” those who work remotely while traveling. Exactly how many fall into this category is difficult to quantify, but with the Digital Nomads Around the World Facebook group at almost 37,000 members and the Webworktravel – Digital Nomad Network page at more than 21,000 members, there is clearly an interest in working while you see the world.

You can do a lot with a laptop and a good Wi-Fi connection, and among nomadic digital workers, professions vary. On any given day in a nomad hub like Chiang Mai, you might meet writers, programmers, designers, SEO experts, affiliate marketers, and dropshippers. You can co-work in the middle of rice fields in Bali, reply to emails on a pristine Thai beach, and network over coffee and arepas in Medellin.

But can globetrotting ever truly be compatible with financial stability and career success? I turned to some veteran digital nomads to find out.

Spend Low, Charge High

My friend Will Moyer, a web and app designer, was living in Beijing and teaching English when he decided to freelance full-time in 2011. Already working with design clients as a side hustle, he craved the autonomy and flexibility of self-employment.

“One of the biggest benefits is you can work with high-paying clients remotely while living in a country with a very low cost of living,” Moyer said.

Another benefit is having the time and flexibility to work on passion projects. When you don’t need to work 50 to 60 hours a week to make ends meet, you can put more energy into developing your own ideas.

In Moyer’s case, this led to his book, Writing for the Web  (edited by yours truly). He’s also the co-host of the podcast “Why Do You Care?!,” a show about movies, television, and other media.

But you have to work for that freedom and flexibility. Unless you’re already versed in contracts, negotiation, and basic money management, there’s a steep learning curve to self-employment. You’re also likely to be hustling for remote clients, some of whom may be wary about working with a contractor in a different time zone. And it’s practically guaranteed that you’ll go through a slow period or encounter unexpected expenses.

“Landing a big client or getting tons of interest from different clients starts to make you feel like ‘Yes, I’ve finally made it.’ But then a dry spell hits and you can’t find work for a couple months and you consider quitting and becoming a bartender,” said Will, who still ascribes to the digital nomad lifestyle, most recently in Colombia and then upstate New York. “I still haven’t really overcome the feast and famine environment of freelancing, but I also haven’t become a bartender—yet.”

Beyond beer and coconut money

When you’re living in places where the cost of living is low and travel is inexpensive, it’s easy to get caught up in the impulse to travel constantly.

When I met Elisa Doucette in 2012, she was the managing editor for The Tropical MBA, a community-based information hub for would-be entrepreneurs and digital nomads. During the next two years, Elisa built her own client base in addition to her Tropical MBA work while living in places like Bali and Chiang Mai. Then in November 2014, she let go of her anchor client and struck out on her own with her business Craft Your Content, an editing and content management agency.

“Leaving Tropical MBA definitely impacted me financially. I lost thousands of dollars in monthly recurring revenue from them, and so there was a brief period of time where I had a coronary,” she said with a laugh.

Elisa was fortunate in that she had already developed a client base during her time at The Tropical MBA, and her colleagues there supported her move by referring people to her. She managed to grow the business into an agency that now does a quarter of a million dollars in revenue annually.

She cautions against people quitting their jobs and moving to the other side of the world without a plan for what they’ll do to make money. Though she says there’s nothing wrong with just wanting to earn “beer and coconut” money, if you’re serious about building a business, you’ll need more hustle than that.

In my experience, going after beer and coconut money can be very fulfilling, just not financially speaking. Taking time to explore the local culture, bond with fellow travelers, and focus on experiences over earnings leads to incredible memories and relationships. However, I also learned that that’s not a sustainable lifestyle in the long term, at least not for me.

“If you’re going to work for yourself, take it seriously,” Elisa said. Instead of traveling year-round as she once did, Elisa now plans to split her time between a home base in New Hampshire and a winter getaway in Mexico. The consistency allows her to focus on growing her company in a way she couldn’t when travel was a higher priority.

“I need to create a lifestyle that’s conducive to allowing me to [build the business],” she said. “It was a little bit sad, and it’s sometimes hard [to turn down travel], but I’m also willing to make the investment. Building the agency to be something I’m proud of, that’s more important to me. I’m at a point in my career where I want to start building the legacy, and building a legacy probably takes more than a four-hour work week.”

The life of an expat entrepreneur

Drew Meyers also began building his company while abroad. He first became a long-term traveler in 2010, visiting South Korea, Japan, Greece, Spain, Kenya, Ghana, and several other countries. He says remote work arrangements weren’t as popular then as they’ve become in recent years.

“It wasn’t exactly easy to find companies willing to pay remote workers to travel the globe in 2010,” he recalled. “Finding remote work is certainly easier now as there are more proven examples of remote teams, but still not as easy as finding a job while living in one spot.”

Meyers made it work by offering social media consulting to U.S.-based real estate companies while he traveled. Then he decided to build Horizon, a travel app that enables people to find places to stay and sublet around the world. He and Will began working together after meeting in Chiang Mai, and Will eventually became a co-founder of Horizon.

Drew said that cheaper costs of living in cities like Chiang Mai and other global hubs for online entrepreneurs are a considerable benefit when building a company. Paying employees and contractors costs less in second- and third-tier cities, allowing for a much longer runway during the company’s early stages. He was able to tap into a network of other entrepreneurs when he and Will brought Horizon to Startup Chile, an accelerator for startups from around the world.

But running a company from abroad also has its drawbacks. “From my experience, it’s very, very hard to raise money without being face to face with investors. There’s simply no way to get 100 percent of their attention over Skype or a phone call,” he said. “Most investors want to invest in people they can see in person. They are putting a lot of faith (and money) into the entrepreneurs they invest in—and most of them have realized what I realized, that building a company while constantly traveling is hard. To them, that means increased risk.”

Like Elisa, Drew eventually decided to seek out a more consistent home base to focus on the company, and he currently lives in his native Seattle.

“Traveling constantly means you spend mental bandwidth figuring out where you’re going to sleep, where to eat, what to do, where to find Wi-Fi, who to hang out with—all things you don’t think about if you ‘live’ somewhere,” Drew said. “Ultimately, I felt if I really wanted to build a lasting company, I should put roots somewhere, and focus on building a company and not on traveling.”

Learn the language, build a business

Not everyone who becomes an expat entrepreneur does so while migrating around the globe. Phil Crimmins arrived in Beijing on a teaching contract in 2011. Realizing he could earn more as a private tutor, he quit his job and went freelance. But his freelance tutoring career was short-lived.

A trained drummer, Phil quickly became plugged into the local music scene and began making more money as a musician than he did as a tutor. However, gigs tend to dry up during the winter in Beijing, and he found himself “totally bankrupt” without those bookings rolling in. So when he was offered a job at the Kempinski Hotel in Chengdu, he headed south, where he performed regularly and was given room and board as part of the gig. After getting to know the city, he decided to stay in Chengdu long-term.

Phil enrolled in a local university to learn Mandarin, knowing he’d have greater success in China if he improved his language skills. After a few years of intensive study, Phil was able to pass the rigorous HSK 6 language exam in roughly half the time expected, giving him a business idea.

“As I continued to get better at Chinese, I realized that the methods I was using were really effective,” he said. “And I realized this was something I could teach other people.”

Now he’s the co-founder of Mandarin Blueprint, offering in-person and Skype language learning services. He and his business partner are also developing online classes that students can access around the world. Though Phil co-hosts the podcast “The Third Eye” and still takes drumming gigs when they arise, Mandarin Blueprint is his main priority now.

“I’ve always thought about being an entrepreneur, since I was in my early 20s, but I was kind of afraid to do it,” Phil said. Now he’s more comfortable financially than at any other point in his life. In addition to starting the company, speaking Mandarin has led to a range of other opportunities, including hosting events and starring in instructional videos, simply because he’s able to network more easily with local business contacts.

Sticking out the tough times is essential for anyone who works for themselves, especially those willing to embrace the extra challenges of doing so abroad. And while having a plan in place before you hop on a plane can mitigate some issues ahead of time, you’ll always encounter problems—MIA clients, stolen laptops, missed opportunities, surprise medical bills. But building up an emergency fund and cultivating fortitude are better strategies than holding out for the perfect moment to take the plunge.

“Save up some money before you do it, but don’t wait for the time when you feel ready and safe. That’ll never happen,” Will advised.