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Peggy Bree, a creative project manager, started by setting up shop remotely in Playa del Carmen, Mexico.HANDOUT

Peggy Bree has been on the move since she graduated from the Ontario College of Art and Design in 2016.

The remote creative project manager started by setting up shop in Playa del Carmen, Mexico, then Bermuda, followed by Thailand. Then, after a few months back home in Toronto, she joined an organized trip for digital nomads like her that included time spent in Peru and the Bahamas.

There’s much to love about the work-from-anywhere lifestyle, Ms. Bree says, such as the ability to spend her weekends in a desert oasis in Peru or an Elephant sanctuary in Thailand.

However, there are also a lot of challenges that aren’t as widely known. Often social media highlights the best parts of the experience without delving into the less publicized challenges.

“The most important thing is to have a full picture of the lifestyle, because I feel like all these entrepreneurs and all these people on social media will tell you just to go for it,” she says in an interview from Santa Marta, her favourite town in Colombia, where she’s lived and worked for the last six months.

Most digital nomads understand the practical problems they can run into, like finding a quiet place to work with strong Internet access and maintaining standard work hours from different time zones. However, Ms. Bree says there’s less awareness of the social sacrifices that often need to be made.

“Nobody really talks about the emotional aspects,” she says. “It looks fun and easy, but those emotional parts, sometimes they catch up with you, like ‘oh wow, I’m missing good quality friendships.’”

She says staying connected with friends at home is difficult because she can’t physically be there with them, while new friendships are hard to maintain because both parties are frequently on the move.

The challenges are so common that it inspired Hacker Paradise, an organization that curates group travel for digital nomads, to add personal connections to its pre-trip checklist.

“Set an alarm on your calendar so that every time you transition to a new destination, you make sure that you are communicating with people [at home] the hours in their time zone that you’re available for a chat,” advises Michaela Murray, Hacker Paradise’s head of marketing, who has lived as a digital nomad.

The career lifestyle has become much more common and accessible since Hacker Paradise began in 2014, particularly since the pandemic, Ms. Murray adds.

“We were making it work for ourselves, but now there’s a landscape and an industry that caters to this,” she says. “There are co-working spaces and co-living spaces popping up all over the place, you’ve got visas that are specific to digital nomads, and destinations are actively trying to draw the nomad crowd.”

While the lifestyle is easier than it was in the past, partly because of improved technology and a greater focus on work-life balance, Ms. Murray warns that it’s also no vacation. She and others in the digital nomad community instead advocate for an approach they refer to as “slow travel.”

“People come on these trips, and sometimes they burn the candle at both ends; they work as hard as they would at home, but during their free time, they push it just as hard,” she says. “We advocate for a slower style of travel, where you aren’t being a tourist, but you’re living more like a local.”

Adapting to the digital nomad lifestyle also requires a certain degree of resilience and flexibility.HANDOUT

Adapting to the digital nomad lifestyle also requires a certain degree of resilience and flexibility, according to Shawn Radcliffe, a Hepworth, Ont.-based writer and yoga teacher who has lived and worked remotely throughout North and Central America.

“There are times where you do have to adapt, where you’re stacking crates or whatever you find in your space to make a desk that works,” Mr. Radcliffe says. “If you’re too fixated on everything being perfect, then work-from-anywhere might not be as pleasant as you think it will be.”

Still, he believes digital nomadism can be the perfect solution to a more remote workforce that is no longer bound by travel restrictions and lockdown measures, especially those in creative fields.

“You live at home, and then once you start working at home, you find that you never leave home, so when you start working from other cities, it kind of shakes your brain up a little bit,” he says. “If you’re a writer or a creative person, I think that it’s beneficial for your work because you’re thinking in different ways as you’re seeing different things.”