Digital nomad who built over 40 startups says it’s normal to ‘feel like a loser’ in your 20s — especially when isolated in a foreign country

Pieter Levels, a self-taught developer (not pictured), said he has lived in 40 countries and 150 cities.

With over 40 startups, self-taught software developer and “indie hacker” Pieter Levels has said he’s been able to bring in millions in revenue right from his laptop while traveling the world.

While that sounds glamorous, it wasn’t always that way. It started with him feeling like a loser in Asia.

“I was making $500 a month or something, and I was looking at the ceiling thinking like, ‘Now I’m 27, I’m a loser,'” he said. “And that’s the moment I started building startups.”

Levels is a digital nomad, a person who works remotely while traveling, and said he’s lived in 40 countries and 150 cities. While it sounds like a perpetual vacation, Levels said in a recent episode of the “Lex Fridman Podcast” that he often felt depressed while trying to establish himself and find success.

“It is romantic, memories of this kind of vagabond, individualistic solo life,” Levels said. “But the thing is, it didn’t make me happy.”

A 2018 study comparing the mental health of ex-pats and domestic US workers found that three times as many ex-pats reported feeling trapped or depressed as their US-based participants. Additionally, of the 455 surveyed expats, 25% expressed feeling anxious or nervous — over twice the rate of US-based workers who participated.

But while expats have the benefit of only having to settle into a single new environment, digital nomads who don’t settle in one spot are constantly having to re-adjust to different places.

“You’re traveling around, you’re hopping from city to city,” Levels said. “You don’t have a home anymore. You feel disrooted.”

Digital nomad and psychologist Carolin Müller previously told B-17 that it is “harder for digital nomads to stay mentally healthy” because of this constant feeling of not understanding and feeling understood.

“You’re never in a stable culture,” she said. “You’re always changing from one culture to another, you’re coming and going, and sometimes you have a culture shock.”

Other digital nomads have expressed similar stories of struggling with feelings of isolation and instability on social media. One person on Reddit described the experience as “profoundly lonely” and eventually had to return home. Another post said that they developed “strong feelings of anxiety and depression” because they missed their family and friends and isolated themselves too much.

Levels said that it can be “psychologically taxing” to travel solo without the comfort of a reliable schedule and rules.yes

“Anything is possible. You can go anywhere. And everybody’s like, ‘Oh, that must be super nice — freedom. You must be very happy,'” Levels said. “And it’s the opposite. I don’t think that makes you happy, I think constraints probably make you happy.”

He said that watching his friends in Holland continue to do well with a normal life made him feel like an “outcast,” especially since he was not as successful then. However, Levels assured people that “it’s normal, if you’re young, that you feel like a loser.”

“Because you have nothing,” he said. “Probably no money, you have no business, you have no job yet.”

So, his solution was to try to make money and build a business — or several. In 2014, Levels launched his “12 Startups in 12 Months” project, where he would create a startup every month and launch it with Stripe.

“Which is kind of an interesting way to deal with depression,” he said. “It’s not like, ‘Oh, let’s talk about it.’ It’s more like, ‘Let’s go do something.'”

While some proved unsuccessful, one of these startups was Nomad List, which Levels claims now generates $48,000 per month, according to Level’s X bio. Based on a spreadsheet he created with other digital nomads, Nomad List is a site for digital nomads that provides data about cities around the world, such as their cost of living, internet speed, and safety.

And while Levels was transparent about the downsides of being a digital nomad, there are also perks, such as the ability to see more of the world and live in locations with lower cost of living.

A decade after launching the site — and many others, including PhotoAI — Levels is continuing to live abroad. Despite the sometimes isolating feeling, he said that traveling from city to city is beautiful and fun, especially with the growing community of digital nomads.

“It’s romantic,” he said. “It’s colorful if I think about the memories.”