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A Guide to Living the Life of a Modern Day Nomad

It’s the stuff of dreams: Trading your traditional nine-to-five slog for the freewheeling lifestyle of a digital nomad. No more commute, no more cubicle, no more office drama—just you, your laptop, and a hammock swinging in a balmy tropical breeze.

See recent posts by Christina Pérez

“The digital nomad lifestyle offers a certain freedom that most people yearn for,” says Amy Schwartz of Unleash, a coworking travel company that caters to surfers. “You don’t have to wait for two weeks a year to see the world, or countdown the years until your retirement to really travel. And you can make your own hours—so you can fit in your work when it is convenient for you.”

Charlie Birch, who recently launched Rebel + Connect, a summit for remote workers, agrees: “People want to feel free—they want their work to enhance their lives. They don’t want to be a slave to the job. “Plus,” she adds, “travel is sexy. With the advancement in technology it is now possible to be a professional success and a lifestyle traveler. Who wouldn’t love this?”

It is precisely those reasons that the phrase “digital nomad” yields almost 4 million search results on Google and books like Tim Ferris’ Four Hour Work Week and Ralph Potts’ Vagabonding—both of which are years old—continue to sell in droves. The appeal of being your own boss and the architect of your own time whilst also seeing the world is undeniable.

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For me, it was all that—plus visions of checking my email between surf sets—that eventually inspired me to leave my own job as a magazine fashion editor to become a freelance lifestyle writer and launch my own travel site, Inside Elsewhere, three years ago. And though that decision eventually enabled me to travel from Peru to Mexico to Bali and beyond while also writing for publications I’d always dreamed of contributing to, the reality of the lifestyle has certainly been different from what I initially expected. From wifi woes that regularly derailed my productivity to watching cherished personal relationships dissolve from afar, there’s no doubt that pursuing my sun-dappled dream of nine-to-five freedom has taken its toll.

“People see gorgeous Instagram photos from far-flung places and are attracted to the digital nomad lifestyle without fully knowing much about it or the inherent daily ups and downs,” says A Modern Wayfarer’s Stefanie Acworth. “Digital nomads are constantly traveling, seeing the world, and meeting interesting people from all walks of life,” agrees Birch. “However, they can also spend 90% of their time in front of a screen. This can have negative impacts on both physical and emotional health. And, it can be a challenge to form strong meaningful professional relationships without location regularity.”

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Knowing all that now, would I change anything about the last three years? Maybe, but not really. Sure, I wish I’d been more realistic about the challenges, but ultimately, pursuing my wanderlust was one of the best personal decisions I’ve ever made—and not just because of the places I’ve been to, but because of the person I’ve found along the way: myself. As Emmanuel Guisset, founder the coliving-coworking company Outsite, puts it: “Whether you like it or not, living a nomadic existence forces you to learn about yourself, what drives you and what makes you tick.” I know I certainly have.

Below, a few veteran nomads reveal the things to keep in mind should you decide to take the plunge yourself.

Ease in

“First you need to find something a job that can allow you to have that lifestyle or create your own business,” says Guisset. “I would start by trying out it a couple of weeks and go live and work somewhere. Then slowly extend those trips and may be make them more permanent.”

Plan Ahead

“Before jumping into the lifestyle it’s wise to have a decent amount of funds saved,” recommends travel writer (and Jetsetter influencer) Michaela Trimble. “As a freelancer, my income rises and dips over the course of many months. I always try to have enough saved for the dips, and I try not to overindulge during the times of greater earning.” Todd Kingston Plummer, another travel writer, agrees: “Sort out your finances before you skip town, and be sure that your income streams are set up to direct deposit.” Otherwise, you may find yourself begging friends or family members to run to the bank to cash a check for you.

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Photos: Courtesy of Michaela Trimble

Be Realistic

“Be aware that working while on the road means you do actually have to get stuff done,” says Acworth. “Deadlines aren’t going to go away and if you want to get paid you need to be disciplined. Sometimes you might have to miss an adventure in favor of logging time on your computer.” Birch agrees: “Becoming a digital nomad is not a cure all. Don’t be fooled by the glamorous #LaptopLifestyle posts on Instagram. Digital nomads are real people with real world problems. Make sure you are making this shift to enhance your life not to escape it.”

Get Connected

If there’s one thing most digital nomads agree on, it’s that tech failures can be one of the biggest derailments to productivity on the road—even in this day of seemingly omnipresent Internet. “No internet. Slow internet. FaceTime/Skype disconnections. The frustration of trying to find good wifi never goes away,” muses Acworth. Becoming a member of a group like Outsite or Unleash, both of which cater to remote workers by providing high tech work spaces, can be a godsend. “Living out of a suitcase is hardly conducive to a productive working environment, especially if you’re having to find a different place to work every day,” says Guisset. “Having access to an actual work space helps with that.”

Stay Balanced

“Even though I don’t have set work hours, I find I’m most productive if I’m waking up at the same time every day,” says Trimble. “Cultivate harmony between the energies of work, play, and rest. Work has to get done, play is appealing, and rest can easily be forgotten until it’s too late,” adds Birch. Guisset agrees: “Finding a community who can inspire you and motivate you will also definitely lead to a better work-life balance. It’s easy to work all the time or relax all the time when you first start. It’s a change.”

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Courtesy of Christina Pérez

Stay Social

“Just because you don’t have a permanent address doesn’t mean you can’t have an active social life—or love life for that matter. “Using Tinder and Bumble abroad has been so much fun—it’s a great way to meet new people,” says Plummer. “It’s a great way to meet locals and have them show you something really authentic.”

Get In Touch

“Be intentional about creating and maintaining human relationships,” says Birch. “Don’t just float in and out of people’s lives or you will get lonely.” Plummer recommends taking advantage of social media, especially in bouts of loneliness: “When your friends are just an Instagram or an email away, the world feels a lot less big. True friends will still blow up your phone from the other side of the globe, and when you reunite it will feel like no time has passed.”

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