How 3 ‘Digital Nomads’ Balance Their Dreams with Long-Term Travel

For some, travel is a pastime; for others, it’s a permanent state of being.

Airbnb booking data highlighted 84 people who’ve been to 20 or more countries just in the year, and others who’ve traveled to dozens, even hundreds of cities using Airbnb.

Some were enjoying extended honeymoons or gap years, while others were retirees savoring  long-awaited world tours. Many others were ‘digital nomads’: People who work as they travel, drawing inspiration from new places and experiences that shape their creative passions.

These types of extended trips are becoming more popular among Airbnb travelers: The number of travelers who racked up 20 or more new passport stamps staying in Airbnb listings over the past 12 months is up 27 percent from a year ago.

We spoke with three long-term travelers on what led them to hit the road permanently – and how they make their dreams flourish without a permanent address.

Rachman Blake | Writer & Comedian | Currently in Mumbai, India

It all started with a breakup. That’s one of the reasons I dove into stand-up comedy. Comedy became therapy for me. So along with some other performers, I started a live show about dating: the good, the bad, and the funny of romance in this day and age.

We traveled around for about a year, and decided that in order for this to work, we’d have to take the show everywhere. We used Facebook ads to gauge interest in our show and found out that there were plenty of people in each major city to pull it off.

We did Romania, and then a new country every week: that’s one of the cool things about Europe. After doing three months of successful shows, we decided to do a worldwide tour.

We always try to book a place to live that’s close to the venue. And the only way to do that consistently is through Airbnb. All you want to do is concentrate on the show, and not worry too much about finding accommodations.

One of the coolest things is being challenged on a daily basis, learning what dating is like in that culture, and putting together a show that works in a culture with a different set of values. We also work with local comedians, collaborating with local acts that can talk about dating in a way that we can’t.

I’ve talked to Airbnb hosts about the local culture, and that perspective helps us to make the show more universal. It’s made us all better performers in the end. We’re more versatile and well-rounded.

We’ve been to over 20 cities, and it will be close to 60 cities over the next year. You definitely see cultural differences in dating – the horror stories really differ – but in all the countries we’ve been to, we’ve all been in agreement that dating sucks.

Ellany Lea | Psychotherapist & Coach | Currently in Madrid, Spain

My parents are Taiwanese, but I was born and raised in Canada. I was a slow-to-start traveler, I wasn’t raised on a cruise ship; my parents weren’t diplomats. I was the eldest in the family, which means it’s my job to take care of all my siblings and my parents. Family is a big thing: You put everyone’s needs before your own. Eventually, my dad retired, and I brought my parents to Vancouver. Then it was like, okay, you’re retired, the brothers are grown up – time to take off traveling.

My original degree was in electrical engineering, but I wanted to go overseas. Just to do real work that matters to people. So I went to Rwanda, and that in a way became an addiction: You meet strangers who take you in, and you bond with. In that work, a lot of the new placements stayed with me, so my apartment became like an Airbnb before Airbnb. Later, when I lost my apartment in Toronto, I found a temporary place on Airbnb. It turned out my host had friends who worked in international aid and we had the greatest conversations. From then on, I’ve only used Airbnb when I travel.

That led me to a job with Doctors without Borders in New York. I was their international online strategist. That led me to leadership training: I got trained and certified as a coach, and then as a psychotherapist.

I started with Nicaragua in 2010, and took my calls there. I wasn’t sure it would work, so I tested it with a client and realized that I could do calls from anywhere. The next year, I went to three countries: France, Italy and Greece. The year after I did 5 or 6 countries. Then the year after that I did 16.

It’s zen’ed me out. And yet, I’m a very structured person. I fly on Mondays, always picking flights that would land mid-day so I’d have the evening to go to the grocery store and get settled in. Then I have Tuesday to walk around, and spend Wednesday and Thursday doing coaching calls. Then Friday, Saturday and Sunday are free to go camping in the desert, diving under the sea, or some other adventure. It might sound surprising, but I thrive on structure.

But if I had done my practice at home, I’d have no reason to be so zen about things. In the sense that stuff happens all the time, from delayed flights to the smallest things like haggling with taxis, and now I’ve been here before and know I can handle it.

By the time you reach country 80-something, you start to realize the world is very small and that we’re all very similar. Once I passed country number 50, I figured why not do them all? I ground myself somewhere for a couple of months, do some heavy lifting with work, then I take off and go country hopping. I’m going to Tunisia and Malta next week: that’ll be 105 and 106. I think I could complete them all in the next two years,  and then I’m pretty sure I’ll keep traveling. I’m so used to this mobile life now, I can’t imagine staying in one place for too long.

Damon & Melissa Maria | Software Developer & Midwife | Currently in Prague, Czechia

Melissa: I was in the middle of renovating the house in New Zealand, and deciding whether to sell it. Damon suggested that we travel together. We started on the the other side of the world: In Hawaii to visit friends, in Buffalo, NY, up to Canada and eventually drove down through Mexico and Central America. I was working with some Mayan midwives as a facilitator for some of their students. Then they needed someone in Bali for a couple of months.

At that point, I was 13 weeks pregnant, so we knew we had to head back to New Zealand for awhile. When our son, Marlowe, was 5 months, we hit the road again. When we first decided to do it, we sold literally everything we owned in New Zealand that didn’t fit in a small backpack. So we definitely were thinking it was going to be long term.

Damon: I work as a software developer. About a year before we left, three of us started up a company. I do the development side, and manage people at the moment back in New Zealand.

Melissa: When we set out, my goal originally was to connect with midwives everywhere we went, to learn about the breadth of midwifery, with aims to get into midwifery on a global level through advocacy, policy or education. Now in October, I’ll be doing some work at a refugee camp through a midwifery organization. And if that goes well, that’s something we’ll continue to do in areas like Iraq, Kurdistan and Greece. It’s a way to stay connected and involved in midwifery worldwide outside of the clinical setting.

But now that we have a child, we travel smarter; and the more we do it, the more we realize what’s going to work and not going to work.

We try to stay at least two weeks in Airbnbs wherever we go. Now, our idea is not to see everything in Prague – that would have to be the main focus. What we’d rather do is get to know our neighborhood very well. Our memories might be of a neighborhood coffee shop. That’s the great thing about Airbnb is that we’re hanging out with locals.

Damon: We try to see ourselves as living in the world. Traveling constantly forces us to go beyond the comfort zone, into the unfamiliar. We also travel with so little, proving that’s all we need.