Digital nomads told us what it’s like to work remotely from around the world — and how you can do it yourself after the pandemic
Tags: Lifestyle, Remote Working, Digital Nomads, Travel, Freelance

By Jessica Poitevien

In 2014, Andrea Valeria was working a full-time job in Hawaii when she negotiated to work from home permanently following a trial period. Her bosses accepted the proposal and she packed her bags for Argentina, the first of many destinations she’d visit as a digital nomad.

Now, the Panama native works from her home base in Mexico City, and runs It’s A Travel O.D., a site that offers resources to help aspiring digital nomads land their first online job.

Defined simply, a digital nomad is someone who earns their living mostly online and uses this location independence to travel as much as they please — usually often.

Valeria told Insider she used to move as frequently as once a month before she started traveling at a slower pace.

“I find that I can be more productive when I’m not constantly having to book flights and look for new apartments all the time,” she said.

When the pandemic hit, however, Valeria had to cancel all of her travel plans. Though she misses traveling, luckily she had established her home base and legal residency in Mexico just months ahead of the pandemic.

Valeria has worked in a number of countries, including Chile. Photo: Courtesy of Andrea Valeria

Before large portions of the workforce were forced to set up shop remotely thanks to the pandemic, digital nomads like Valeria had already mastered the art of working from home. And now, more people are joining the ranks of this once obscure lifestyle.

In 2019, 7.3 million Americans described themselves as digital nomads in a study by independent talent provider MBO Partners. That number represents an increase of 2.5 million people from the previous year.

And as tech giants like Twitter make a more permanent switch to remote work, other companies both big and small are expected to follow suit, paving the way for a post-pandemic increase in digital nomadism.

Digital nomads don’t have to be bloggers with a huge social media presence — they just need to work online

At first glance, the digital nomad world is dominated by IT, marketing, and communications professionals, and those who offer creative services like writing, editing, or graphic design. But a deeper dive reveals a community with work experiences as diverse as their nationalities: There are voice actors, accountants, lawyers, virtual assistants, event planners, life coaches, business development managers, HR recruiters, translators, consultants, and more.

“You don’t have to be a blogger or have any kind of following on social media. That’s a big misconception,” Valeria said. “You just have to make money online. Some people are freelancers and have multiple clients, some work full-time for one employer, and some people are business owners. Your work setup is up to you.”

Valeria works from her home base in Mexico between trips. Photo: Courtesy of Andrea Valeria

To build your own digital nomad lifestyle, you need to secure an online income. Then comes the more exciting part of the journey: choosing where to go.

Wanda Duncan, who has been a digital nomad for five years, describes herself as a “slow, solo traveler,” and says she usually stays in a country for one to three months, often the duration of her visa there. This year, however, Duncan’s travel plans looked a little different; she’s spent most of 2020 sheltering in place in Malaysia — a home base she wasn’t planning on but is making the best of.

According to Duncan, it’s a common misbelief that digital nomads are constantly working from the beach and jetting off to new destinations every week, living life like a tourist.

“While for some that’s surely possible, folks that want to long-term travel sustainably are usually paying monthly rent and washing dishes in another country,” she told Insider.

Wanda Duncan says the digital-nomad experience is different to that of a tourist. Photo: Courtesy of Wanda Duncan

When choosing how and where to spend their time, some digital nomads opt for consistent life on the road, while others have a home base they can return to.

Wherever digital nomads are, they need a steady internet connection

One thing everyone agreed on is the importance of a speedy internet connection.

Kim Leary, who has worked in 25 countries so far, advises scoping out how reliable the internet connection will be in the area you plan to work from, and recommends having a plan B — like a cell phone plan that allows you to use your device as a hotspot — if something goes wrong.

It’s also a good idea to research local cafes and coworking spaces with Wi-Fi. Most importantly, Leary always gives herself some extra time to settle into life in any new location. This way, she can solve any issues — internet or otherwise — before she has to start working.

Unfortunately for Leary, at the beginning of the pandemic she lost the travel industry job that helped her start her nomadic journey, but she’s not giving up on the lifestyle. Now, she’s back in her hometown of Seattle, looking for tech industry jobs in the hopes of finding a company with the flexibility that will allow her to continue digital nomading, even if it’s just part-time.

Kim Leary took a break from work to visit Ecuador’s Cajas National Park. Photo: Courtesy of Kim Leary

Certain destinations have become hot spots for remote workers

For plenty of coworking spaces, cafes, and affordable housing, digital nomads often flock to Medellin, Lisbon, Bali, Chiang Mai, and more recently Tbilisi, Georgia.

In an effort to draw more digital nomads and the economic boosts they often bring, some countries have created new visas specifically geared towards remote workers.

While Estonia launched its e-residency program in 2014, places like Georgia, Barbados, and Bermuda announced similar initiatives this year. They join a growing list of nations — like Mexico, Germany, and Spain — with self-employment visas that could apply to digital nomads.

Insider reporter Rachel Hosie visited Barbados to try its work-remote lifestyle. Photo: Rachel Hosie/Insider

Life as a digital nomad can look glamorous, but it comes with its own set of challenges

Unreliable internet, frustrating visa processes, and balancing work and play are all par for the course in this lifestyle, but another common challenge of digital nomadism is fighting loneliness on the road.

“There’s this balance between wanting to explore and see things just because we can, and also creating this sense of community,” Leary, who maintained a home base in South America throughout most of her digital-nomad journey, said. She suggests staying in one place for at least a month and using coworking spaces to add structure to the workday and meet other people.

Leary made friends with a llama in Peru. Photo: Courtesy of Kim Leary

Both Duncan and Valeria point to social media as a great resource with plenty of support groups for expats and digital nomads. Other options include joining a gym, attending local events, and using websites like Couchsurfing to connect with travelers around the world, though these may not be viable or safe options during the pandemic.

Noticing a lack of community specifically for Black women in the digital-nomad space, Duncan decided to create her own, running a Facebook group, podcast, and an annual conference all for Black women travelers.

“All of my work is geared towards empowering other Black women who are interested in leaving [the US], but lack confidence, skills, or a support system,” Duncan said.

There are also companies like Remote Year, Hacker Paradise, and WiFi Tribe that curate trips for remote workers looking for more structured digital nomading and a sense of community. Companies like these often take care of accommodations, coworking spaces, and transportation between destinations, though it’s worth noting that some of these have paused or adjusted their services for the time being.

Despite limitations on travel during the pandemic, aspiring digital nomads can still prepare for the lifestyle in future

While traveling in the pandemic isn’t a good idea, digital nomads say now is a good time to develop remote-working skills that could one day translate to future travel opportunities.

Leary believes anyone aspiring to be a digital nomad can prepare themselves for the lifestyle, whether they are working from home or not. Leary, who worked at Boeing for 10 years prior to becoming a digital nomad, suggests building up professional experiences that will stand out on virtual job applications.

“There’s a certain amount of professionality and foundation that you need for a lot of jobs, especially in a virtual work environment where you have to be accountable to both yourself and your client. I feel like a lot of that is developed ‘in the office,’” Leary said. “Having that foundation is key. It makes you a lot more desirable for these employers that do allow virtual work environments.”

It’s worth noting that many people, including frontline workers, are not able to do their jobs from home, but that doesn’t mean there aren’t remote-work opportunities in healthcare or other fields that seem to require in-person interactions. Many medical professionals have opted for virtual visits; there are nurse hotlines, travel nurses, health insurance case managers, and more. With a little creativity, there are ways to find remote work in many industries.

Valeria used to travel as often as once a month. Now, she’s slowed down a bit. Photo: Courtesy of Andrea Valeria

As for those going back to a reopened office, Duncan says now is the time to negotiate.

“When approaching the conversation, highlight how much of an asset you are to the company, and how productive you’ve been able to remain if you’ve been remote already,” she said. “If you haven’t been remote, suggest a trial remote period of three months.”

And while the logistics of securing work and appropriate visas are important, Duncan also urges digital nomads to take care of their emotional, physical, and mental needs as well.

“Some people think they leave their problems behind,” she said. “It’s true where you go, there you are. In fact, in some ways your situation — insecurities, depression, self-doubt, etc. — can be exacerbated.”

“Learn boundaries not to pour yourself into your laptop all day, every day,” she added. “And remember to nurture a hobby or two for funsies.”

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