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Skillshare // The Trials, Triumphs of Being a Digital Nomad

Skillshare // The Trials, Triumphs of Being a Digital Nomad

'The Trials And Triumphs Of Being A Digital Nomad' was originally printed by Skillshare on May 16, 2018. Written By Rachel Gorman

A generation ago, traditional nine-to-fivers may have dreamt about ditching the grind to live on a beach somewhere, but unless they were independently wealthy (or very comfortable with risk) the financial realities of that idea were probably insurmountable. As technology has advanced and telecommunications has made remote-based work more common however, the dream of leaving the office behind and traveling the world indefinitely no longer seems as far-fetched. In fact, many workers have already made it a reality.

Since 2014, the international community of “Digital Nomads” (or, as some people prefer, “location independent”) people who carve out a way to earn a living while they traverse the globe has seen an undeniable uptick in its numbers - and in its hold on the popular American imagination. A cursory Google search reveals that there are thousands of personal blogs dedicated to becoming a Digital Nomad, and more than 1 million public Instagram posts that feature the hashtag #digitalnomad in their descriptions (to say nothing of the hundreds of thousands of others posted under #digitalnomadlife#digitalnomads, and similarly-themed variants). Dozens of media outlets, including The New York Times, Forbes Magazine, and BBC News among others, have filed stories on Digital Nomads in recent months, and National Geographic has an ongoing blog dedicated explicitly to sharing tips, tricks, and photos from people who advocate the lifestyle. Skillshare too, has thrown its hat into the ring, interviewing illustrator, graphic design expert and Top Teacher Cat Coquillette on her Digital Nomad lifestyle in January of this year.

Hundreds of Miles and a Click Away from the Working World

For anyone who has felt stuck in an office environment or experienced the pang of wanderlust, the appeal of “having it all,” or at least, location independence and financial stability, seems obvious. Though there are exceptions, Digital Nomads are primarily young, entrepreneurial, creative, from developed nations, and tech-savvy. Many, like consultant Tim Hammond, post photographs on Instagram that showcase glamorous, adventurous and exotic experiences - images far from the everyday toils of those constrained to an office life or mortgage.

Hammond, a Digital Nomad from a small town in Northern Michigan, describes his initial attraction to the lifestyle as a “desire to feel as though I was fully living my own life, rather than cramming myself into a mold structured by someone else.” He moved to Washington, DC and became an analyst for a defense contractor, but found that he didn’t want to “assimilate [into] a culture where people hold their breath for the weekend” and started a business that would allow him to work remotely full-time. After awhile, he says, he felt like he was “wasting money paying expensive rent when I could use that money to fund experiences” and although it was initially “quite challenging to let go of a traditional livelihood,” these days he’s motivated by the prospect of new adventures. “Now, when there’s an idea or dream of going somewhere, it’s an actual possibility” he says, adding that, as an uncle of eight, “the ability to see my family more is another huge perk.”

 Being a digital nomad doesn't mean working every day from a beach chair, but if you want, you can. 

Being a digital nomad doesn't mean working every day from a beach chair, but if you want, you can. 

Proponents of the Digital Nomad lifestyle talk openly about how meaningful and satisfying their experiences are, and how financially sustainable they are too, particularly for those who stay responsible by traveling in regions with lower costs. Some argue that it’s simply a matter of time before the lifestyle becomes the norm. According to an independent survey commissioned by the Freelancers Union, more than 53 million Americans, or roughly 34% of the nation’s workforce, already identify as working freelance. With remote work, cheap flights, and global high-speed internet so prevalent, some argue that it won’t be long before a large subset of the global workforce becomes nomadic. After all, when you can work from anywhere, why wouldn’t you?

Matt Gillespie, a full-time web designer and Digital Nomad with his wife and toddler, hints at exactly that question with his blog unsettledown.com. After leaving an unsustainable lifestyle in California, Gillespie and his family have traveled Europe and along the way “saved more and paid off more of our student loans in the last year than we ever have” he reports. There’s been spiritual and social benefits, too. “You can create a life for yourself unlike anyone has before. The opportunity to travel and sustain your career and family growth...never has ‘working to live’ had so much potential” Gillespie says.“I wouldn’t change a single step along this path my family and I have set ourselves upon.”

 Matt holding 20-month-old Kailen during a transition day from Lucca, Italy to Riomaggiore. 

Matt holding 20-month-old Kailen during a transition day from Lucca, Italy to Riomaggiore. 

The Lonely Road

Yet for some, living the dream of working while traveling can feel like a real nightmare. For all of his zeal, Gillespie is also open about how difficult traveling can be. “I was extremely stressed at first, to be frank. There isn't so much of a cultural shock to process as a home-life shock, if that makes sense” he says, adding that “traveling full time is definitely less sustainable in terms of the wear and tear it takes on you...it's hard moving everything you use daily once a month or once a week and live out of suitcases or backpacks.” Particularly if you are traveling, as he is, with a small child in tow.

“Watching my daughter fearlessly face new challenges and language barriers...is so rewarding. She honestly has handled the rigors of constant motion better than my wife and I have” Gillespie says, but even with their added benefits, he adds that the churn of “new places and sleeping spaces, new languages and cultures, and constantly crossing into new time zones test our ability to keep her daily life consistent” and create unique challenges for his family.

Digital Nomads also talk about difficulties maintaining passports and work visas, finding adequate global health insurance (to say nothing of health care), and forcing oneself to get comfortable with shifting local laws and customs. They worry about food and water safetythe uncertainty of finding peace and quietpersonal and professional safety, challenges with weak wifi signals, time zone differences, and for some, feelings of being isolated and lonely as they try to maintain long-distance relationships while living life on the road (Gillespie notes that one of the hardest parts of his traveling experience has been when his daughter has had to “say goodbye to her little friends, cousins, aunts, uncles, and grandparents” as they have moved from place to place).

There are more existential challenges that Digital Nomads must consider, as well. On a popular Reddit message board that asks “What are the Worst Things about Being a Digital Nomad?” many posters commonly and frankly discuss how, despite the egalitarian promises of commuting from anywhere, their lifestyle is considerably easier for people who are independently affluent, or who have a significant savings cushion to rely on as they travel. Unexpected costs come up, some say, and freelance work can prove to be less than consistent. Workers with regularly-paying remote jobs report feeling unmoored from colleagues back home, and many discuss being constantly stressed about money, or at least acutely aware that they have less job security, no benefits, and no social safety net.

Nicole Faith is a location independent entrepreneur who worked remotely at Squarespace before leaving to found 10 Carat Creations, a Concept Concierge service that helps freelancers craft their own location independent businesses. She says that “as a self-motivated individual, this style of working really suited me” but even after she became a freelancer, her transition to becoming fully location independent was far from quick. “I had saved a lot of money that allowed me to be entrepreneurial and work thousands of unpaid hours on my business.” she says. “Escaping the 9-5 is possible, but you still need to work. Work is work, whether you’re in an office, at home in your pajamas or on the beach.”

“If anyone tells you they just up and left and now run a super successful business, they are lying, getting financial support, or living on poverty level in other countries” she adds.

Hammond, too, is honest about being dogged by the financial concerns that can come with being a long-term Digital Nomad. “The biggest drawback for me personally is the anxiety that comes with not having a “normal” job and the stabilizing benefits that come along with that. You have to let go of certain comforts.” he says.

In location independent communities, there are common concerns about a lack of clear delineation between work life and leisure time. Some, like Nathan Yates, Digital Nomad and remote CEO of WYCO, welcome “work-life integration” as a hopeful, or at least realistic, development for present and future workers. His upcoming presentation at this year’s DNX Festival, an annual Digital Nomad “Mega-Event,” promises to discuss how the very idea of work-life balance is a relic of the industrial economy and a non-starter for today’s global commuter. But other Digital Nomads that contend with blurred personal and professional boundaries report feeling exhausted and overwhelmed with navigating work stress and unfamiliar cultural environments. When she first began her business, Faith reports that she had a difficult time managing her schedule. She notes that having unlimited options is a benefit to location independence, but says that for her, choice can “also be a drawback sometimes. I can go to the beach.. or I can write a blog. I can go out for breakfast.. or I can go through my emails. It’s a constant negotiation in my head to find the right balance.” She says when she first began, she felt so much guilt and pressure to work that she “overworked myself when I should have enjoyed my location.” These days she knows that when it’s time to get real work done, she has to shy away from traveling. “The people who harp on the [traveling aspects of the] lifestyle likely aren’t selling anything of value. The business comes before the dream, always.”

Of course for people who live in regions that regularly play host to those working remotely, the uptick in roving professionals has its own set of benefits and challenges. There is the influx of money that long-term travelers bring to an economy, a sense of global interconnectedness, and a breakdown in calcified cultural barriers. On the other hand, when privileged Digital Nomads aren’t conscious of their effect on a region and don’t seek out local vendors, cuisine, or experiences (particularly when traveling in the developing world), they run the risk of compounding inequity and culturally or economically displacing the very communities they profess to cherish.

Prepare Before You Pack

Even with its challenges in full view, the rise of international travel and easy telecommuting means that the lure of becoming a Digital Nomad isn’t going anywhere. For those considering a leap into the lifestyle, proponents say it is critical to keep in mind the potential drawbacks as well as promised pleasures, and to make contingency plans for worst-case scenarios before heading out on to the open road. “Reconsider this lifestyle change five more times after you think you've made up your mind...if you think you're 100% on board with selling everything and living on the road, think again,” Gillespie says. “Play devil's advocate. Go through the best and worst-case [sic] scenarios and weigh each out. Make pro and con lists. Make a budget, and then add 30% more expenses to your total and budget again.”

Along with saving extra money, Digital Nomads say, honestly assess your priorities, propensity for loneliness, freelance expertise, and your tendency toward overwork. Faith says she sees “see people with a strong sense of self who are independent and curious being great digital nomads” but “without the internal motivation to build a business and not just a fancy lifestyle, your time on the beach will be short-lived.” She says the best thing to do is to “spend time with yourself, exploring your interests, strengths and weaknesses. It’s not very glamorous but it is enlightening.” If you understand your motivations for living on the road, you’ll have a more positive experience when you actually set out.

Think it through, prepare well, and if you’re still feeling excited about traveling, then becoming a Digital Nomad might just be the best decision you’ve ever made. After all, as Faith says, “We’re at a point in history where working from anywhere is completely possible, so the only thing stopping you is you.”

 Matt and Kailen, August 2017, determined to leave their mark on Lake Garda, Italy. 

Matt and Kailen, August 2017, determined to leave their mark on Lake Garda, Italy. 

6 Steps for Budgeting Life as a Digital Nomad

6 Steps for Budgeting Life as a Digital Nomad