Illustration by Justin Tran
Illustration by Justin Tran

Virtual First

Is it actually fun to work as a digital nomad?

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Published on September 21, 2021

Illustration by Justin Tran

Stories and advice from the far frontiers of remote work.

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Cubicle life just wasn’t for Kristin. As a former champion surfer, she first developed a taste for nomadic life 17 years ago while traveling to surf competitions and studying abroad. 

“I lived in Costa Rica for a semester and learned Spanish,” she recalls. “Then I did a semester in Australia, studying international business, and coincidentally learned how to do corporate relocation.”

When she returned to her home state of Florida, she got a job offer that landed her in an office park in Orlando five days a week. “I just couldn't do it,” she says. 

In 2005, she took a job at a real estate company in Costa Rica. “I was there for the boom and the crash. That started my love of living abroad.”

Six years later, she decided to start her own relocation company. “Through that, I started helping people move to countries that I wasn't even living in,” she recalls. “I thought, ‘If I can do my job from anywhere, why am I taking time off work to go travel when I could just work and travel at the same time?’”

Once her lease was up, she packed up her stuff, put it in storage, and hit the road. She’s been traveling full time ever since. A few years ago, she had the idea to start creating content to help more people learn how to become digital nomads. “I didn't really see this movement taking off for another 10 years,” says Kristin. “But I guess the world had different plans.”

As luck would have it, following her passion took her to the crossroads of two key cultural trends: the creator economy and digital nomadism. For the past 15 years, she’s been building a business as a location-independent entrepreneur. Now she not only advises people on how to relocate other countries, she offers practical tips to aspiring digital nomads through her website, podcast, and YouTube channel.

Though it wasn’t her original goal to become a content creator, she saw growing appetite for stories from the digital nomad community. So she bought a GoPro camera and began watching tutorials to learn how to make and edit her own videos. 

“Trying to do YouTube, podcasting, and writing at the same time, I think I learned faster because I was able to compare and contrast those experiences and learn content marketing from a broader perspective,” she recalls. “Why is this blog post performing better? Why is this video getting more views? I've used Dropbox throughout throughout that time for file sharing, commenting on the videos, and collaborating with my editor. That's been really helpful.”

“I started by just documenting my travels while working remotely,” she explains. “Then I started interviewing interesting people I met so I could tell their stories. That's how the podcast was born. It's been a crash course on going from zero to 100,000 subscribers. It's taken my brain a little time to catch up with the identity of being a content creator. But it's a lot of fun.”

Though Kristin was fortunate to have a head start as a digital nomad and content creator before both fields exploded in popularity last year, many others have just begun exploring these new frontiers. They’re not the typical freelance creatives or even the waves of workers escaping burnout as part of The Great Resignation. This is a new wave of nomads who are actually retaining their full-time jobs. Harvard Business Review recently reported on a new study that shows the number of digital nomads rising from 7.3 million in 2019 to 10.9 million in 2020.  

“I didn't really see this movement taking off for another 10 years, but I guess the world had different plans.”—Kristin

One of the authors of the study, Steve King, founding partner at Emergent Research, says the research revealed that in 2019 over 60% of digital nomads were self-employed independent workers, whereas only 35% had traditional full-time jobs. But in 2020, that ratio flipped. 

“The pandemic didn't actually accelerate the number of independent workers who became digital nomads by very much,” says King. “A lot of them had the flexibility to be digital nomads before and simply chosen not to do it. But meanwhile, we've unleashed all of these traditional job holders from their desks. A lot of them said, ‘Hey, I can travel now.’ We think the number of people who have the ability to be digital nomads will be much larger in 2022, than it was in 2019.”

Untethered from their offices, full-time employees now make up a majority of those taking their work to go. So how are new nomads navigating the obstacles of working without an office while traveling during a pandemic?

Full-time freedom beats part-time freelance

Working remotely from northern Africa, Kate is a writer, researcher, and video editor who recently shifted from freelancing for several employers to working full-time for one. “I liked the freedom of freelance, but the pay wasn’t as great, nor stable,” she says. “It felt like a Frankenstein career: $20 for an article here, $70 here, $10 here. A salaried position with a fully remote company is fantastic.”

“I’ve always been very wanderlusty, even when I lived in the [U.S.] working full-time in healthcare,” says Kate. “I decided to save up to travel for a year or two, but then COVID hit, and I met somebody overseas, and I just decided to go for it. I figured if I didn’t make any money, I could always go back to the states and start over. But I did end up making money, so I’ll be doing this indefinitely.”

Kate says she thinks the modern digital nomad lifestyle is an offshoot of vagabondism. “I’ve always been super inspired by people who have been able to travel and blog. Explore full time! Paid to see the world! Unfortunately, I feel like ‘traveling the world’ became more about Instagram influencers and get-rich-quick-on-an-island schemes. [Digital nomadism] is sort of a more adult, realistic version of that.”

Though she loves the freedom, it comes with many caveats. “You are ultimately free to go wherever you want, but everywhere has its own constraints. For example, my husband is from Africa. Our visa is limited based on where he can go, which limits our options to around 60 countries unless we want to fill out the lengthy and expensive visa, which he might get denied.”

Budget is another limitation. When Kate and her husband are weighing where to live, they also have to factor in Covid restrictions and proximity to home in case of emergency. 

“It gets overwhelming pretty fast,” she says. “We do what I call ‘slowmad,’ which is just traveling slowly. A new country every 6-12 months, and week trips in between as work and finances allow. I had this unrealistic idea of freedom when I decided to start this lifestyle. I thought I could work from anywhere, and then I went literally anywhere, and realized I needed to be anywhere with Internet.”

Kate says life as a digital nomad has given her a lot of insight into modern work culture and just how dehumanizing it can be. “Being in control of my time made me realize that punching in and out of a normal workplace was hard on my mental health in ways I didn’t realize before. Having a flexible work schedule has been great because it really allows me to focus on my family and my work without having to split myself apart into these neat little boxes where I feel like I’m failing all the time.”

“We do what I call ‘slowmad,’ which is just traveling slowly. A new country every 6-12 months, and week trips in between as work and finances allow.”—Kate

Kate says life as a digital nomad has given her a lot of insight into modern work culture and just how dehumanizing it can be. “Being in control of my time made me realize that punching in and out of a normal workplace was hard on my mental health in ways I didn’t realize before. Having a flexible work schedule has been great because it really allows me to focus on my family and my work without having to split myself apart into these neat little boxes where I feel like I’m failing all the time.”

When you’re working on the other side of the planet from your coworkers, though, scheduling calls and Zoom meetings can be tough. “I'm in North Africa, my family is back in Alaska,” says Kate. “My work is over 5 different time zones. A nap is like Russian roulette.”

To stay connected to her team, Kate video chats with them at least once a day. Though that can limit her freedom of movement, she considers it a good trade off. 

“The collaboration gets tricky with time zones and coordinating efforts,” she says. “We’ve had to get creative about using different tools and SaaS that let us work synchronously and asynchronously. Thankfully, my work has been doing the remote thing long before me, so they had a great infrastructure in place.”

Lean into local, forgo your comfort zone

LB is a product manager based in Spain who works remotely with a team of software developers. The nomadic lifestyle provided a way for LB’s family to spend extended time with other family members and friends around the world. “We quickly realized how enriching of an experience it was to be a nomad, for us but especially for our child,” LB says. 

It’s given LB a chance to meet new people and experience new parts of the world on a deeper level. “I've traveled extensively throughout my life, but there is something different about establishing your daily routines in new area,” they explain. “Finding a place to grab coffee, becoming familiar with local markets, learning how to navigate public transport—even dealing with local bureaucracies can be a bit of an adventure.”

Spending months in the heart of big cities can also provide a glimpse beyond tourist traps. “The same can be said for sleepy beach towns off season that are virtually empty,” says LB. "I feel like we’ve seen dimensions of the country that even many locals don't get to see.”

Like many digital nomads, LB initially found it tricky to navigate time zones and stay aware of office politics from the other side of the world. “It's a bit stressful and mentally taxing to reestablish your life and routines in a new area,” says LB. “I have teams all over the world: US, Mexico, and India. I have also worked with teams in Russia , Peru, and Argentina. Being in the middle of the time zones has its challenges but also the benefit of overlapping North America and Asia, thus opening opportunities to facilitate communication that would otherwise be disjointed.” 

LB advises new nomads to explore several places, find one with a vibe you connect with, then spend an extended amount of time there. Try to speak the language and learn the nuances of the local culture. Connecting with expats can be comfortable, but it won’t help you fit in. “Local political tensions, economic conditions, crime, etc. can really influence the mindset of people,” says LB. “Try to understand these issues and make sure you are making a positive impact on the community.”

Don’t forget your paperclip

Ben is a UK citizen who recently began working as a digital nomad and documenting his new life with video tours of his travels in Estonia and Latvia. He says the first thing to emphasize about being a digital nomad is that it isn't a holiday. 

“You might be in the nicest location, sun shining outside, waves lapping on the shore—but you've still gotta have that two-hour meeting,” says Ben. “It takes a bit of getting used to, like you're wasting ‘holiday time’ by being sat inside on the laptop.”

Explore several places, find one with a vibe you connect with, then spend an extended amount of time there, says LB.

One of the biggest challenges has been dealing with Covid certificates and shifting guidance—a struggle that is all more real for Americans now that the EU has removed the US from its safe list. Though Ben’s been fully vaccinated and has the necessary QR codes as proof, most European countries don't recognize his NHS Covid pass since the UK left the European Union.

“I can get into the countries without issue, but getting into gyms, cinemas, restaurants, etc. is not possible,” says Ben. “That's something I've not seen mentioned before but is obviously quite debilitating.”

Ben’s original idea was to start in Tallinn, Estonia’s capital, then head south and move counter-clockwise around the Black Sea. “My third stop would've been Belarus, which is now off the cards due to the political situation in the country,” he explains. “All land borders are closed and there's no flights in until at least November.”

Due to the UK/EU COVID Pass issue, he thinks he’ll need to bounce out of Europe for a bit. That brings him to an important point all aspiring nomads should keep in mind. “Always keep an eye out for what's happening in the world,” he says. “Plan a few countries ahead. Every day, I check the standard news sites, but also sites like Reddit and Slack. These have subs for countries and continents, and often give a better feel for what's happening on the ground.”

He also recommends downloading Google Translate and whichever bus, tram, or transport app is needed for each new location—”plus, whatever app the little electric scooters use.” And bring a paperclip so you can change SIM cards with each country. Ben has lost count of “the amount of times I've had to beg, borrow or steal pins, paperclips, and name badges from cashiers.”

Ask for permission or forgiveness?

Though you might be tempted to, say, take off for South America without telling your team, most experienced nomads recommend communicating your plans and negotiating the terms with your employer before you take the leap.

“Always keep an eye out for what's happening in the world,” says Ben. “Plan a few countries ahead.”

“I actually have an article and video on how to convince your boss to let you work remotely,” says Kristin. “Some companies are letting people spend one or two months a year living in other countries, then come back. Some people don't want to be fully nomadic. They just want the flexibility to travel more. So it's about getting clear on what you're asking for first.”

Kristin also suggests thinking about it from your employer’s perspective. “Look at the company culture and assess ‘How difficult will this be? Are there examples of other people in the company doing something similar?’ Build your case. Think about who to approach. Who are the decision makers? What are the issues that could concern them? Find those answers out for yourself before you go to them.”

Kristin says if there’s resistance to right now and your company’s not quite ready to let you try life as a nomad, you might have more options soon. “There's a tidal wave pushing in this direction.”