How to Work Remotely for a Year and Travel the World

By Linda Knittel, Editor-in-Chief

As a writer, I can technically do my job from anywhere. And while I adore Portland, Oregon, where I have lived the last couple of decades, I do romanticize the idea of traipsing around the world—writing stories from exotic locales. That’s why I was so intrigued when my friend and colleague Nancy Levenson told me she was heading out with Remote Year, a program that brings together 75 like-minded yet different individuals from around the world to travel together to places like Croatia and Morocco and work remotely.

In addition to an instant community of friends that travel with you to a new city each month, participating in Remote Year means you don’t have to worry about travel arrangements, lodging or work spaces—it’s all organized for you. And while it’s not an inexpensive program—a $5,000 down payment and then $2,000 a month—that cost covers all travel between destinations, accommodations, workspaces and Wi-Fi, and community activities.

After returning from her year abroad, I spoke with Levenson about her time as a digital nomad.

Calmful Living: Why did you choose Remote Year rather than travel on your own or with a friend?

Nancy Levenson: As much as I’d like to say I love solo travel, I just don’t. I want to share the experience. And while I know a lot of people who love traveling as much as I do, I didn’t know anyone who was ready to travel for longer than a few weeks at a time. I also liked the idea that Remote Year was taking care of details such as where we’d live and how we’d get from place to place. It seemed like a good way to ease into long-term travel.

CL: Did you already have all your work lined up for the year?

NL: I have a pretty steady stream of work as a freelance writer, and I’ve been doing it remotely for a few years, so that didn’t change. I am deadline driven no matter where I am, and I didn’t have a problem hitting my deadlines when I was traveling. However, if I didn’t have a deadline looming over my head, it was definitely harder to focus on work when there were so many tempting things to do and see.

CL: In general, how were the work, living and travel accommodations provided?

NL: Accommodations were inconsistent. Sometimes I lived in a brand-new building within walking distance of tons of great shops and restaurants. Other times, my apartment was a bit dingy or overlooked the highway. When we were on our way to a new city, everyone held their breath in anticipation of what apartment they’d get. We traveled by plane pretty much everywhere; so that was fine. I endured one long, stinky bus ride between Prague and Belgrade.

CL: What was the hardest part about Remote Year?

NL: One of the themes of embarking on an experience like this is getting out of your comfort zone. I really appreciate getting out of mine. But I didn’t realize that I’d be out of it for months at a time. That’s truly uncomfortable! I definitely missed being in a familiar place sometimes, and I often longed to be with people who knew me well. Also, because Remote Year chooses the cities you’re going to and the places you’ll live, that’s out of your hands. The lack of control can be challenging for me.

CL: What was the biggest lesson you learned about yourself during Remote Year?

NL: I learned that I’m pretty darn adaptable and that I can roll with a lot of different situations. I think I have the right kind of personality for travel because I accept that things will go wrong, and when they do, I tend to stay calm and I can still enjoy myself. I also learned that I don’t need a lot of “stuff” and that I don’t love living in big cities.

CL: What observations did you make about people in general?

NL: I always try to look for what we have in common. People are people. At the most basic level, we all crave kindness, compassion and connection. Also, there are an endless number of ways to live, and humans are extremely resilient.

CL: What was the craziest thing you ate?

NL: I’m not sure this would be considered crazy, but it was definitely amazing. In Mexico City, I had a torta filled with fried chicken, chilaquiles, queso and crema. (Chilaquiles are tortilla strips drenched in sauce.) Wow, so decadent and so good! I needed a nap afterward.

CL: What advice would you give someone wanting to create a remote career and travel like you did?

NL: I’d recommend doing it in stages. I know there are people who quit their desk jobs, move to Thailand and start online businesses; but for most people, that’s just too much at once. Take one step at a time. For example, see if you can work at home a few days a week with your current job. Or look into side jobs you can do from anywhere, and start there. Also, start saving money and put it aside for the transition. This way, you’ll be more prepared to take a leap when it’s time.