The Telecommunity: Interview with Author & Digital Nomad Nora Dunn

Coming out the other side of this pandemic, companies are going to be looking at the expensive real estate they own, with regard to office space, and realize there’s another way of doing business. That way of doing business will create a new and more permanent wave of remote workers.
Nora Dunn, Author of How to Get Free Accommodation Around the World and Founder of “The Professional Hobo”

In 2006, Nora Dunn was a Certified Financial Planner (CFP) working in Toronto, helping people engineer their finances to attain the life that they wanted. But in doing so, she’d put her own lifelong dream on the backburner: a dream to travel the world not just as a vacation, but in a way that would allow her to truly crack the code of the places she visited.

To achieve that dream, she realized, required a total change of lifestyle. So she sold her financial planning practice and began what would become 12 years of constant travel, establishing herself as The Professional Hobo in the process.

“I realized, all right: I can’t live a life of regrets,” Dunn says. “So I sold everything I owned, with no idea of where I would go, what I would do, or how I would make money. By the way, I don’t recommend that!”

In making the decision to change her life, Dunn cast herself as one of the world’s first digital nomads, long before ‘digital nomad’ was a mainstream term. Across 60 countries and five continents, Dunn blazed a trail for those who would come after her. Along the way she’s apprenticed in shamanic ceremonies in South America, chronicled the Victorian Bush Fires in Australia, and traveled 25,000 kilometers by train from Lisbon to Saigon. One of the things that helped her lifestyle transition become a success was the balance between spontaneity and practicality.

“The financial planner in me never died,” Dunn says. “My financial house was in order before I left. I made sure I had savings. I’d taken care of my debts. I didn’t burn any bridges that I didn’t necessarily want to burn. All that gave me a sense of security while throwing myself into a life of total unknowns.”

That financial good sense is still apparent on Dunn’s blog, where she publishes regular financial case studies of other full-time travelers. A common theme amongst them is that the emphasis need not be on the quantity of one’s earnings, but rather the quality of one’s spending.

That theme carries over to Dunn’s book, How to Get Free Accommodation Around the World, which was borne out of Dunn’s experiences housesitting, volunteering, and ultimately saving over $100,000 on accommodation while traveling.

“I traveled full time in a financially sustainable way, even in the early years, when my business wasn’t making anything, because I didn’t spend more than I made,” Dunn says. “Part of the reason for that is I was volunteering in trade for free accommodation, which created really enriching experiences around the world that I would have never had if I was just staying in a hotel, a hostel, or even renting an apartment of my own. It’s one of the best things I ever did.”

The Third Wave of Remote Workers

Since starting her journey over a decade ago, Dunn has witnessed two distinct waves of remote workers:

  • The first wave, which includes Dunn, involves a more entrepreneurial spirit: remote workers who had to forge their own path and make it up as they went.
  • The second wave, which followed in the first’s footsteps, is made up of established remote workers who are supplemented by the gig economy, steady contract work, and more stable location-independent careers.

“There’s going to be a third wave,” Dunn says. “Because of the pandemic, companies around the world have been forced to find a way to have their employees work remotely. Coming out the other side of this pandemic, companies are going to be looking at the expensive real estate they own, with regard to office space, and realize there’s another way of doing business. That way of doing business will create a new and more permanent wave of remote workers.”

Another factor that may contribute to this third wave of remote workers is the digital and physical infrastructure carved out by the first two waves. Cities like Chiang Mai, which had previously been little more than stopovers for the most diligent of backpackers, have become major hubs for remote work, with the infrastructure to match. It’s now possible for a remote worker to show up in Chiang Mai and quickly find a month-to-month furnished condo, strong Wi-Fi, and a bevy of coworking spaces to accommodate them. Entire countries—Barbados, Georgia, and Estonia, to name a few—have begun to roll out long-term visas specifically to entice remote workers.

“If my prediction is correct, and there’s going to be a new wave of remote workers exercising their ability to take to the road for as long as they want, then there will be new industries and new things cropping up to enable that to happen,” Dunn says. “But a large percentage of people, I think, are still going to work from home. They may have the ability and desire to take longer trips, but they may not sell everything they own and live completely nomadically. Though they could if they wanted to.”

Advice for New Remote Workers

Dunn knows better than most that the transition to remote work can have a steep learning curve. As the effects of the most recent pandemic change the modern definitions of work, of travel, and of vacation, a whole new cohort of remote workers will need to make adjustments, and many will be looking to people like Dunn for guidance.

“The biggest piece of advice I can give to anyone who is location-independent and is a remote worker is to be clear about the lines of work and play,” Dunn says. “You can do that in a few different ways. Within the space that you’re living, if you’re going to be working from home, create a workspace. Create a workspace that you can walk away from when you’re not working because the lines blur really quickly. Work-life balance has consistently been one of the largest challenges I’ve had, and honestly continue to have.”

Setting boundaries for oneself is a constant struggle in the remote work lifestyle. The modern expectation of instant responses to work emails can’t easily align with a global workforce spread out across different time zones. And in lieu of a traditional office, remote workers have to be mindful of the environments that they choose to designate as workspaces.

“I used to work in a cubicle and for a long time I couldn’t imagine paying exorbitantly for that privilege through a coworking space,” Dunn says. “But they can impart the benefits of creating a specific workspace, satisfying ergonomic requirements, creating a community with other remote workers, and allowing one to leave work at work. Coworking spaces can be a great way to achieve a better work-life balance, it just comes at a cost.”

Finding Balance and Connection as a Remote Worker

Constant travel has its costs, too—and not just financial.

For Dunn, each new city and each new country has meant packing her life back down into a bag. Even with long stops along the way—anywhere from three months to two years at a time—that bag got emotionally heavier to pack and lift. That’s part of the reason why, in 2018, Dunn decided to make a semi-permanent home base back in Toronto.

“Living nomadically has a shelf life,” Dunn says. “There are exceptions, but somewhere around the ten-year mark, people burn out of the lifestyle. The ex-pat community and the digital nomad community are great, but they’re very transient. There’s something to be said for connection, and having long term connections with people.”

A home base hasn’t voided the concept of travel in Dunn’s mind, though it has redefined it. In 2019 she traveled to six countries, with a strong focus on destinations within the Americas. Those travels have been in balance with her time back in Toronto, where she’s reconnecting with her family and friends and setting down roots. Now 14 years into her journey, Dunn is still redefining what’s important and calibrating her life to match. Looking back, she has no regrets.

“If I’m proud of anything, I guess I’m proud of having listened to my intuition in 2006 that this was a good idea, and followed my dream, and had faith that everything would work out because it did,” Dunn says. “There was no rulebook, there was no online course. I had to just get out there and learn it all from the ground up, and make every mistake you could possibly make. But I’m still here to tell the story.”

Matt Zbrog
Matt Zbrog

Matt Zbrog is a writer and freelancer who has been living abroad since 2016. His nonfiction has been published by Euromaidan Press, Cirrus Gallery, and Our Thursday. Both his writing and his experience abroad are shaped by seeking out alternative lifestyles and counterculture movements, especially in developing nations. You can follow his travels through Eastern Europe and Central Asia on Instagram at @weirdviewmirror. He’s recently finished his second novel, and is in no hurry to publish it.

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