Working remotely from a tropical beach is tougher than it looks

Imagine this: You finish your work for the day, press "Send" to email files to your boss, then lean back in your chair, toss your feet up, and gaze out at the turquoise water and white sand beach.

And no, it's not a screen saver.

Untethered to a desk, a commute, or a mortgage, digital nomads use technology to work remotely, earning a living while they travel the world.

But while the thought of working from a tropical locale can be an intoxicating fantasy during these dreary days of winter, it's not without its challenges. Indeed, much of the culture is built around perpetuating a dream, so cubicle workers can live vicariously through the brave few who are able to make a go of the nomadic lifestyle — often with no mention of the drawbacks of such radical freedom.

It wasn't that long ago that the concept of a person just plugging in to the digital world from wherever they happened to be was a futuristic scene out of a cyberpunk William Gibson novel.

But the technologies we've come to take for granted in our daily lives — high-speed wireless internet and user-friendly production tools and platforms — have enabled entire economies built around digital culture, social media and online influence, and have made that science fiction reality.

Hubs for nomads

In turn, destinations around the world, from Chiang Mai, Thailand, to Medellin, Colombia, have become hubs for digital nomads, attracting "location-independent" freelancing travellers with an attractive combination of temperate climates, breathtaking scenery, reliable Wi-Fi, co-working spaces and a low cost of living.

According to a Gallup survey, over half the U.S. population already works remotely, at least some of the time, and this number is increasing.

"We can attribute the uptick in remote work to a confluence of factors; the most obvious, of course, is the staggering growth of internet and mobile communication," says Brooke Erin Duffy, an assistant professor in the department of communication at Cornell University, who notes that organizations are facing mounting pressure to provide more flexible work schedules to accommodate their employees.

Indeed, says Pat Lau, a Toronto-based visual effects artist, while 90 per cent of his clients are local, he's never met most of them in person.

"I try not to form the habit of going to a studio unless it's necessary," he says. "If they ask me to come in, usually I decline, or ask if I can do the work remotely."

Essentially, says Lau, it doesn't matter where he is when he's working. And while that currently means he can avoid a gruelling commute, his goal is to relocate to a more exotic setting.

Others have already made that leap.

"I was on a path to live a traditional lifestyle," says Kate Smith, who has been travelling the world and working remotely since 2015. She lives in Bali and runs an immersive training program that shows people "how to get started with working online," as well as a blog called The Remote Nomad that promises to help readers "create a life with more freedom and fulfilment."

Scrolling through popular social media platforms, it would seem that, like Smith, many of the most prominent digital nomads support themselves by documenting their travels, sharing their experiences and teaching others how to do the same.

Indeed, while there are no doubt many less visible digital nomads quietly working in graphic design or online marketing, the top related search results on YouTube feature lessons and tips on how to be a digital nomad, and how to make money while travelling and working remotely.

'Think in a different way'

So what does it take to make the dream a reality?

"People think they need to be a developer or overly tech savvy, but that's not true," says Smith. "It really comes down to learning how to think in a different way … it takes a lot of hard work, but it's possible."

But Duffy cautions, "The idea of overnight success is often a mythical one that conceals everything that goes on behind the scenes or, in this case, behind the screens."

She says, as with any type of social media career, the meritocratic notion that "with talent, anyone can do it," is a central part of its cultural resonance.

Ironically, given the time commitment required to build and maintain a loyal online following, many of the most visible digital nomads don't necessarily enjoy the very freedom they promote so enthusiastically.

Dan Johnston, a self-proclaimed digital nomad, runs a YouTube channel called Dreams Around the World filled with videos such as "How to work for yourself and travel full time."

He says he's encountered workaholics who sell freedom because that's what they think people want, but they're not living that. "They're really selling how to make money online, and look at all this freedom, but they're ultimately working 60 hours a week."

Of all of the visitors to Smith's blog, or Johnston's YouTube channel, only a fraction will  follow the lessons they proffer, to actually become a digital nomad.

And for those who are able to make a go of it financially, a new set of challenges present themselves.

Less glamorous side

The less glamorous elements of the nomadic lifestyle "are strategically concealed," says Duffy.

"We've seen a wider idealization of independent work in recent years, and the celebration of the digital nomad is a key place to witness how certain features of this workstyle get underplayed," Duffy explains. She cites the intermittent nature of employment, the lack of stability or benefits and, notably, the social repercussions.

As Smith admits, being a nomad can be really lonely.

"It's difficult to find other people that have the flexibility to live this lifestyle. It's hard to have people come and go in your life. It's the most difficult part."

Johnston points out that many of the services offered in hubs that target digital nomads are designed to address the inevitable loneliness of the lifestyle, by fostering a sense of community with "things like workstations, or co-living, or co-working."

So maybe there's a tradeoff between those brave enough to leave it all behind and those who stay closer to home, perhaps chained to a desk and committed to a mortgage, but with the benefit of friends and community.

After all, we all need to dream, and if we can't be gazing off at a sparkling turquoise ocean, at least we can scroll through an Instagram version.