How traveling for a year changed a remote workers life

4 min read
Josh Catone
  •  Jul 6, 2017
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A year ago Sean Tierney, Director of Sales at WordPress hosting company Pagely, was in a rut. His career was humming along nicely, and he had a good life in Phoenix, but something still felt off. He was stuck in a routine, grinding away at work, while most of his friends in the area were settling down and starting families. His creativity had hit a wall and though he loved his job, he was having trouble staying inspired.

Then a friend and neighbor stopped over one evening to tell Tierney about a program he’d just been accepted to called Remote Year. Along with 70 or so other people, his friend would travel the world for a year, working and living in a new city each month. They’d head across Europe, Africa, and Central America, from Belgrade, Lisbon, and Prague to Bogotá, Medellín, Cordoba, and half a dozen more.

“If you could become a digital nomad, why wouldn’t you?”

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As Tierney listened to his friend, he got excited: maybe this was the solution to his creative block.

Jumping in

The decision to become a digital nomad isn’t an easy one. Life on the road can be deeply rewarding, but it also has its share of big challenges, not least of which is the immensity of the travel logistics to make it all happen.

Related: 50 things only remote workers understand

Tierney had wanted to spend a year roadtripping and working across the US, but balked at the effort involved in planning it all out. “I just looked at the logistics of it and the overhead associated with having to plan all that while simultaneously being effective and working, and I couldn’t have done it,” he says of his road trip aspirations.

But Remote Year solved those big issues. The program would take care of all the planning and logistics of international travel, all Tierney had to do was show up. Suddenly, he didn’t have any excuses not to apply for the program. He was already working remotely for Pagely, and now the burden of planning had been lifted.

“If you can do it, why wouldn’t you?” reasoned Tierney.

The only thing left, once he was accepted and made the decision to go, was getting his boss on board. Because Pagely’s workforce is already 100% distributed, Tierney hoped it wouldn’t be an issue if his location became a bit more fluid over the next year. He sent his boss a message on Slack and by the next morning, he had an answer: “Sean, I don’t care which continent you deliver results from. Just keep kicking ass.” Game on.

Traveling the world for fun and profit

For Tierney, becoming a digital nomad provided the clearer headspace he hoped would reboot his professional career. When all was said and done, Tierney reports that he had one of his most productive years ever over the past 12 months traveling the globe. He was able to build a new knowledge base for his company, create a personalized automated sales follow-up system, more than double the size of his team, and help grow the company’s year-over-year revenue by 90%.

“It’s hard to be creative when you do the same thing every day.”

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Why was a year abroad so helpful for Tierney’s productivity? He attributes his added success to 3 factors that participating in Remote Year created.


The rut that Tierney felt he was in when living in Arizona was partially due to being stuck in the same routine. It’s hard to be creative when you’re always working from the same home office, always stopping in at the same coffee shop. Remote Year was an eject button for that rut, pulling Tierney out of his daily routine and thrusting him into a completely new set of sights, sounds, people, and challenges each month.

Related: Remote workers share how they manage their work-life balance

“There is absolutely an unquantifiable value to being in these places,” said Tierney at a talk he gave at the PressNomics conference earlier this year. “Surrounding yourself with novel situations, diverse cultures, people, situations that put you outside of your comfort zone.”

Tierney attributes these new experiences to opening up his mind and allowing him the creative space to think about the problems he was facing at work in new ways.


“I undervalued this,” Tierney says of the community relationships he forged during his year abroad. “Going into it I thought [Remote Year] was going to be a travel company—solving the logistical issues of this type of travel. What I didn’t assign value to was this notion that there would be 75 other people who you’d become really close with.”

That’s probably not an accident. Michelle Lakness, who does business development for Remote Year, tells me they specifically look for people who will be active in building the Remote Year community, both during the 12-month program and after with alumni and future participants.

Building these new connections with this group of like-minded people (who Tierney describes as “all super interesting”) is another reason he was able to bust out of his rut. Tierney now counts the people in his Remote Year cohort among his closest friends. A group of them already have plans to meetup in Lisbon in July now that the program is over.

“Networks nurture creativity.”

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Support networks can be hard to build for remote workers, and doubly so for digital nomads. But networks nurture creativity, so finding that support group is a vital part of Tierney’s newfound success. Jumping into the digital nomad lifestyle through a group travel program like Remote Year made it easier for Tierney to build and nurture those friendships and connections.


Becoming a digital nomad is scary. There’s a lot of self-doubt that creeps in when you prepare to make the jump. Can I really do my job anywhere? What if I get lonely or homesick? Will I be able to fit into all these new places?

“It’s a huge and scary decision to jump into this, even with Remote Year,” says Tierney. “Selling a bunch of stuff, storing my car, closing my lease… There was definitely a tipping point where I had to be like, ‘I’m all in, I’m doing this. I know this is scary, but I’m doing it.’”

But once he made that leap and realized he could do it, Tierney found a new level of confidence that has paid dividends in both his professional and personal lives. “Once you get over that tipping point there’s a momentum that builds and works in your favor. It’s just a matter of getting over that hump to actually commit to it,” he says.

Personal growth is the name of the game for Remote Year, says Lakness. “We do believe that through travel people can become more open-minded, tolerant, empathetic individuals,” she says, adding that some people participate for more mundane reasons, like becoming better writers by forcing themselves to start a daily travel blog. “I’d say growth in some facet is all that we hope for in the end.”

Your brain on digital nomadism

It turns out, travel changes you.Twitter Logo The things Tierney thought he experienced—expanded creativity, confidence, boosted productivity—are backed up by scientific research. Tierney describes the day-to-day of digital nomadism as a string of little challenges that force your brain to constantly adapt.

“There’s cognitive load you just don’t have in regular domestic life,” he says. From figuring out how and where to do your laundry to deciphering a new kind of toilet to communicating in a foreign tongue, digital nomads come up against dozens of mini-challenges each day.

“Travel changes you.”

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“But those are kind of a good thing,” says Tierney. “It knocks you off kilter in a good way. Those constant novel challenges incessantly blow your mind in a way that awakens you.”

That mental strain is actually really good for brain health, according to neuroscientists. Exposing yourself to new, difficult, or complex challenges literally causes your brain to expand and create denser connections, increasing your mental capacity. Travel, it turns out, is one of the very best ways to put your brain in that situation, according to University of Pittsburgh adjunct professor of neurological surgery Paul Nussbaum.

“Travel by definition is dropping your brain into a place that’s novel and complex,” he told the Chicago Tribune. “You’re stunned a little bit, and your brain reacts by being engaged, and you begin to process on a deep level.”

Remember the things Tierney felt changing as he traveled? Research is also finding those to be demonstrable benefits of travel. Boosted creativity? Check. A study by Columbia Business School professor Adam Galinsky of fashion designers found that those who traveled abroad produced work that reviewers rated as more creative. Greater confidence? Check. Research published in the Journal of Personality and Social Psychology found that students who spent time traveling tended to be be more extroverted after returning home and showed increased emotional stability and willingness to try new things. The positive effects of building community? Check. Research in the journal Psychological Science found that sharing experiences with others makes them feel more intense (the so-called “sharing effect,” which has been demonstrated in other studies). It follows that by sharing his travel experiences with a few dozen other people, the positive effects that accrued to Tierney may have been that much stronger.

How to become a digital nomad

So a life on the road has some clear benefits, and the type of urban nomadism, living and working wherever you please that famed media theorist Marshall McLuhan dreamed about in the 1960s and 70s is now finally technologically possible. But the digital nomad lifestyle is clearly not for everyone. Lakness says successful Remote Year participants tend to be “highly-motivated, passionate, and ambitious individuals” who “come on this experience with an open mind and recognize that traveling and disrupting your life in such a way isn’t easy.”

“Sell your stuff. Pack a bag. Book a flight.”

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But how do you know if this is something you should do and how do you actually make it happen?

The obvious first question to ask yourself is, can you do this? Do you have a job that will allow you to stay financially solvent and work from the road (or if not, can you get one)? More importantly, with that job can you afford to make it as a digital nomad? In many cases, the nomadic lifestyle costs less than a typical “stationary” life in America, but it’s not always as cheap as people think. Remote Year, for example, costs $27,000 for the 12-month program, which includes travel, accommodations, and coworking spots (but not food or other personal costs, which they say typically costs another $1,000-$2,000 per month). Use a service like NomadList or Teleport to get a sense of how much your planned travel will cost.

John O’Nolan, the founder of open-source publishing platform Ghost and a longtime digital nomad, says that he’s run into a lot of folks, often Americans fleeing unemployment or lousy job markets at home, who assume life on the road will be the cure for their financial ills. Those people often end up struggling, he says, barely getting by when their dreams of making money as travel bloggers inevitably don’t pan out.

Also ask yourself if you have personal relationships or obligations that would make extended world travel difficult. Do you need to care for a sick parent? Do you have a spouse or significant other who is unwilling to come along? Tierney related the story of a Remote Year participant who decided to keep an existing relationship going long distance while on the program. It didn’t end well.

“Becoming a digital nomad comes down to just making the leap.”

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Once you have those things sorted, the rest is just logistics and overcoming the fear.

The fear is something that everyone deals with at first, but once you dive in, you sink or swim. You hate it and you move back home, or you love it and realize it wasn’t such a big deal after all.

“The uncertainty is unsettling to everyone. Honestly most people try to make a much bigger deal out of it than it really is,” says O’Nolan. “Sell your stuff. Pack a bag. Book a flight. As with all of life’s most impactful decisions, there’s nothing complicated about it, but it somehow never feels like the right time. Spoiler: whether it’s going nomad, breaking up with a partner, quitting smoking, or committing to learning a new skill—there’s never a right time. You either do it or you don’t do it.”

Logistically, there can be hassles, from arranging accommodations and visas to determining taxation and finding healthcare. Tierney recommends a program like Remote Year for those apprehensive about figuring out the ins and outs of travel on their own. He describes the program as an aircraft carrier: “It’s a traveling home base where you have a social network and very predictable support structure. It’s an easy way to wade into this style of travel,” he says.

Remote Year is the best known option, but a growing number of programs, like Hacker Paradise, We Roam, and WiFi Tribe, offer a similar concept. (O’Nolan is less impressed with this sort of program: “it still sounds a lot more like a gap year than a work year, based on the people I’ve met doing it,” he says.)

In the end, becoming a digital nomad comes down to just making the leap.Twitter Logo

Or, as Tierney puts it: “Everyone who hears about it is like, ‘Oh, I wish I could do that.’ Well, you can do that. The question is, will you?”

Did you enjoy this post? Keep reading about remote work—6 things remote companies must do to build great culture.

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