Digital Nomads Share Biggest Regrets And What They Wish They Knew Before Moving Abroad
Digital Nomads Share Biggest Regrets And What They Wish They Knew Before Moving Abroad
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Digital Nomads Share Biggest Regrets And What They Wish They Knew Before Moving Abroad

Contributor,Kaitlyn McInnis,Kristin Palitza 🕒︎ 2025-10-20

Copyright forbes

Digital Nomads Share Biggest Regrets And What They Wish They Knew Before Moving Abroad

(Photo by Kristin Palitza/picture alliance via Getty Images) dpa/picture alliance via Getty Images The digital nomad lifestyle seems incredibly alluring on social media: all working from the beach with a cocktail in hand, jetting from city to city and making the most of remote work or business ownership. And while being a digital nomad certainly has its perks, there are certain downsides to the lifestyle that should be taken into consideration before making the jump into full-time travel with a business laptop in tow. Here’s what current and former digital nomads and business owners had to say about what they wish they knew about the lifestyle before finding themselves on the other side of the world, trying to keep up with work. It leaves a permanent longing for more “My family and I have lived as digital nomads twice now. My honest regret is that no one tells you the “after” part: once you’ve lived with that level of freedom, it’s incredibly hard to go back to normal life,” said Erin Carey, founder and director of Roam Generation. “We even sold our boat and bought a house, thinking we were done. We tried to settle, tried to tell ourselves we were content, tried to be grateful for the life we had, but in the end, we bought the same boat back the minute we saw it was for sale. That’s the paradox I wish I’d known. Nomad life doesn’t last forever, but the longing it leaves is permanent.” It can cause a slowdown in business and creativity “My biggest regret as a digital nomad wasn't the loneliness or Wi-Fi woes—it was the unexpected erosion of my creative process. I'm the founder of a global tech company, and I initially thrived on the novelty of coding from a Lisbon café or taking a strategy call from a Toronto park. The 'inspiration' was intoxicating,” said Alex Kratko, founder & CEO of Snov.io, a NYC-headquartered SaaS platform. “But I learned that true, deep work (the kind that builds a company) requires a different kind of soil. Constant movement fractured my focus. I was collecting experiences, but I wasn't building anything new; I was just executing from a series of temporary desks,” explained Kratko. “My most significant breakthroughs didn't happen watching a sunset in Bali, but during a quiet, uninterrupted month in a rented apartment in Kyiv, where the only view was my own thinking.” It can be mentally draining “It was mentally draining to constantly have to juggle visa runs, renewals, and changing entry rules,” explained Jeremy Greenburg, Chief Information Officer at SlickTrip. “I definitely underestimated just how much time I would spend solely on maintaining legal status in a country I was staying in.” It’s hard to stay productive “I also had some issues with maintaining an efficient and consistent work-life structure. I sometimes struggled to find reliable Wi-Fi and a quiet workspace on some days,” added Greenburg. “I'll also admit that it was sometimes hard to stay productive across time zones, because there were so many new experiences I wanted to try and places I wanted to check out each day. Staying on top of all of my daily work tasks really required discipline and planning.” It can be financially unstable “I also have to drill in the importance of having a financial safety net. As a digital nomad, you can experience travel disruptions (missed trains, etc.) that lead to you having to spend more than you budgeted for,” pointed out Greenburg. “And what if you unfortunately get sick or hurt and have to go to a local hospital? Or, what if there are unexpected layoffs at your company and you are suddenly without a steady source of income? That is why it's paramount to have six months of savings and travel insurance with remote-work coverage.” It’s hard to make long-term plans “The uncertainty of visas, time zones, and logistics made it hard for anyone — personally or professionally — to make long-term plans,” explained Arsen Misakyan, CEO and founder of LAXcar. “As appealing as it is to live the dream of a ‘digital nomad’, the reality is that without discipline, you’ll end up at something that resembles ‘traveling burnout’ on an adventure high.” It can be really lonely “I find that being a digital nomad is so incredibly romanticized that people often forget the things you are giving up,” said Dóra Jónsdóttir, digital marketing director at a tour company in Iceland. “No one tells you how incredibly lonely it can be. After a while you start to miss belonging to a community, the relaxed feeling of catching up with old friends that simply know you inside out, and simply the comfort of familiarity be it a place, language, or the culture.” To sustain the lifestyle, Jónsdóttir said that you really need to redefine what ‘home’ means to you. “I've been lucky enough to have my partner in crime along with me for the last 5 years of work and travel life, along with our two pups. That's been my community and my 'home' no matter where we are.” It’s hard to build a routine “I found that the constant movement disrupted deep work and meaningful relationships. Eventually, I realized that freedom without structure can feel like chaos in disguise,” explained Vedran Markovic, founder & CEO, MIAV Media. “What I miss most now are the serendipitous routines, knowing the café owner’s name, having a gym nearby, being part of a community.” “If I were to do it again, I’d slow travel: stay at least twelve months in each place, set clear work hours, and plan visa logistics far in advance,” added Markovic. “The digital nomad lifestyle can absolutely work but only if you design stability into the freedom.” Editorial StandardsReprints & Permissions

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