What It’s Like to Wander the World as a Digital Nomad

See recent posts by Kelsey Blodget

In the first article of this series, we asked experts what it's really like to quit your job and move to a vacation destination. The rest of the series focuses on the experiences of people who've actually done it. This installment tells the story of Charlie Ives and Brittany Bennett, who travel the world as digital nomads. 


If you’ve never heard the term “digital nomad,” you’re not the only one — Brittany Bennett and Charlie Ives often have a hard time explaining their lifestyle to people back home. “In the states it’s a relatively a new concept.
It’s not so widely used,” she tells me over Skype from Chiang Mai, Thailand

But digital nomads are just what they sound like: People who travel while making their living off of the Internet.  


“There’s a ton of people in Southeast Asia all working from their laptops,” Charlie explains. He and Brittany decided to pursue a “location independent” lifestyle two years ago, despite concerns from friends and family back home. Brittany had a stable job as an executive assistant for a consulting firm, and Charlie was trading currency and commodities for himself. Brittany says her father in particular was very concerned about her giving up a job with good benefits.

“I don’t think he could point out Thailand on a map. He thinks we’re living over here in a mud hut. It took him a long time to come to terms with what we were doing,” she says. 

Initially, she and Charlie hoped to make money off of Charlie’s currency trading activities, which is how their travel blog, The Trading Travelers, got its name. After selling almost everything they owned, they moved to Khon Kaen, Thailand, where Charlie had invested in a restaurant with a friend. 


Things didn’t get off to a great start. Brittany had a hard time fitting in: Most of the expats in the area were male, and it was difficult for her to get around since she neither spoke nor read Thai, and does not drive. “I was very dependent on Charlie for everything,” she says. Charlie says that in Khon Kaen, “if you’re a blond-headed female, you stick out like a sore thumb.” 

On top of that, the currency trading wasn’t providing a sustainable income. The trading game was changing fast, and Charlie’s strategy of trading wasn’t working well anymore. The two had to adapt. Though Charlie wasn’t ready to give up on trading just yet, he and Brittany started to experiment with affiliate marketing based on a friend’s suggestion. In a nutshell, their work involves setting up websites to review niche products, and linking those products to Amazon; Brittany and Charlie get a commission from those links.

Getting those websites off the ground was slow going. “There was a lot of doubt over the course of a year and a half. No one really understood what we were doing,” Charlie says. But even though people from back home didn’t understand, Charlie and Brittany soon found a community that did. After a few months in Khon Kaen, they moved to Chiang Mai, which Charlie describes as “the mecca of digital nomads.” 

Check out Oyster’s honest reviews and photos of hotels in Chiang Mai, Thailand >>


Throughout this period, Charlie and Brittany logged a lot of miles across Thailand and other parts of Southeast Asia, many of them on a motorbike. They took their bike on a ferry across the Mekong River into Laos (not without difficulty), swam at the Kuang Si Waterfalls near Luang Prabang, went on a jet ski and eagle watching tour in Langkawi, Malaysia, and visited the temples in Angkor, Cambodia, among other adventures. 

But when they were back in Chiang Mai, for the most part, they were hard at work. “People think we’re just goofing off riding elephants, but most days we’re in a coffee shop working sunup to sundown,” Brittany says. 


Making money was still a problem; eventually Charlie had to give up trading altogether and focus entirely on affiliate marketing. “It was a rough start. It took us the better part of nine months to see any income,” he says. 

Finally, though, their work started to pay off in a big way. Brittany has now surpassed the income she had as an executive assistant. “Every day we’re kind of blown away by how successful we’ve been. At this time last year we were ready to throw in the towel,” she says.  

They spent this last summer traveling around Europe, visiting seven countries in two and a half months. They house sat in France and Germany to help pay for their travel expenses, and found that they prefer “slow travel,” which allows them to balance their adventures with working. At the time of our conversation, they were spending two weeks in Chiang Mai before heading to New Zealand for a few months, where they will both house sit and rough it for a few weeks in a camper van. 


Brittany admits that constantly moving around can be tiring, though, and that she and Charlie are considering settling down. “We’ll always travel, but we’ll also find
somewhere that we want to base ourselves long-term and maybe take one or two
big trips a year and not be on the road all the time.” They plan to stay away from a computer for at least two or three months a year. 

But they’re not planning to move back to the U.S. anytime soon — in part because staying out of the country for 330 days a year allows them to qualify for the foreign-earned income tax exclusion. “You stand to save money by living a dream
lifestyle,” Charlie says. 

His advice for would-be digital nomads is not to not spend too much time planning, which can lead to analysis paralysis. “Do something, screw it up. You’re going to learn
way more by doing it rather than reading.”

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