If you open an email from Kaleen Weiland, Ph.D., you are likely to be greeted with “kalimera” rather than “aloha.” That’s because the Hawaii-based mom, wife and director at Blazar Technology Solutions is a digital nomad currently working in Greece, where “kalimera” is how you say good morning.
Weiland’s family found themselves at a crossroads when her 4-year-old daughter Ashlan was just a few weeks shy of the kindergarten cutoff at the school she attended. “This prompted us to consider a different and perhaps more enriching path for her and us. With living expenses soaring post-COVID, coupled with these questions of school, we began exploring the possibility of enrolling her in a school abroad,” Weiland says.
At the time, her husband, Mike, had just successfully closed Series A funding for his company Govly and was navigating pressure to meet serious milestones. Weiland was also breaking records at her company.
“This pivotal moment required us to carefully consider how we could strike an optimal balance between our ambitious career objectives and our aspiration for a more enriched and adventurous family life,” she says. “Despite the inherent challenges and our initial hesitations, our collective yearning for a life that blended professional achievement with personal exploration and growth propelled us forward.”
Here’s how it went.
Digital nomad companies help you see the world
With two successful careers and a near school-aged daughter, you don’t just pack up and hit the road. There are many logistics to consider. That’s when Weiland found Boundless Life, a company that helps digital nomads organize their journeys. Within 24 hours of chatting with the company, Weiland put a deposit down on a three-month journey living and working abroad in Syros, Greece. It’s a location she hadn’t even heard of before. Now, she struggles with the thought of leaving Syros.
Boundless Life is one of multiple companies that organize logistics for digital nomads by planning full programs, often with hosts in various locations travelers might not have considered living and working. Instead of trying to integrate abruptly into a new culture and sometimes a new language, companies like Boundless Life have a ready-made network to help digital nomads feel at home while abroad.
“The local team here in Syros has been incredibly supportive, helping us with everything from dentist appointments to birthday celebrations to finding the best spots for after-work drinks. Their spirit of support and love shines, showing how much they care about the well-being and success of each family,” Weiland says. “They’re deeply familiar with the location and culture, guiding us to connect with the broader community in a genuine and impactful way.”
Weiland shares how, one morning, the Syros event manager with Boundless Life led several families on a hike, sharing the history and unique geography of this special island in the Aegean. “It was the perfect way to start my day before dialing back into work,” she recalls.
Schooling and Boundless Life
But what about Ashlan’s schooling? Her school in Hawaii granted her a three-month “leave” to see the world, and she’ll head back with friendships and memories from Greece. One benefit of working with a company like Boundless Life, Weiland shares, is that she was better able to balance work and parenting abroad, and Ashlan’s Boundless Life school is within walking distance of where the family is staying.
“If a work call unexpectedly extends, I can quickly reach out to our Boundless Life community via WhatsApp to ask for someone to pick up Ashlan. The response is instant, with multiple offers to take the kids for a playdate, allowing Mike and me to finish up. While we have wonderful friends back home, the ease of finding support here is significantly greater,” she says.
Their colleagues weren’t immediately on board, though, and she says they were met with some resistance based on the lack of precedence. “Most people operate from a place of fear when faced with the unknown. And this lifestyle is unknown to most especially productive, high-performing professionals. We had to take extra steps to make our team comfortable,” Weiland says, noting that she’d even put together slide decks explaining the program and the standards they’d hold themselves to. The three months served as a trial period for them, as they’ll likely try digital nomading for a year next.
“Once we were able to prove the concept was effective, we could tell our teams that this is now our lifestyle, and we plan to do a yearlong program,” Weiland says. “Our goal was to create a tangible example showing that living and working abroad could foster a healthier, more productive workforce due to increased happiness, reduced stress and a supportive community, and I truly believe we accomplished this goal and more.”
Edges of Earth and Remote Year—for solo nomads
While solo traveling and working allows much more flexibility and fewer logistics than a family, using a travel company ensures all the odds and ends are taken care of.
Andi Cross is a digital nomad, growth strategist and expedition lead for Edges of Earth, a New York-based company mixing storytelling, travel and diving. “This lifestyle suits those who relish navigating through unpredictable challenges, finding joy in the spontaneity and learning from the inevitable deviations from Plan A,” she says. “However, for those less inclined toward this level of uncertainty and complexity, enlisting professional support becomes extremely helpful. It ensures that important aspects of life and work are managed effectively, allowing for a richer, more fulfilling travel experience.”
Companies also provide solo travelers with a sense of community. For example, digital nomad company Remote Year offers over 20 locations, each with a member-exclusive marketplace that allows members to book amenities or services, sign up for events and adventures and attend meetups or educational opportunities with other nomads. More than 5,000 digital nomads have worked with them, from shorter one-month trips starting at $2,000 to yearlong journeys at $33,000, which includes 12 countries in 12 months.
Hacker Paradise and “hand picked” destinations
Nomads can also rest assured that they will have access to quiet workspaces and reliable 24/7 Wi-Fi, which can be a concern when your job relies on a strong connection to your employer’s virtual meetings and projects.
Finally, nomads might not want to guess which location is perfect for them. For example, companies like Hacker Paradise “hand pick” destinations like Spain, Italy, India, Indonesia, Japan, Belize, Mexico, Sweden, France, Peru and Antarctica.
Boundless Life co-founder Elodie Ferchaud says that while people might expect to see consultants, entrepreneurs and tech professionals as digital nomads, the diversity in their program goes much beyond that, which is a unique opportunity for otherwise solo workers to expand their personal and professional horizons. “We also proudly host artists, health care workers and more. Imagine engaging in inspiring conversations with a fellow digital nomad… in Tuscany,” she says.
So, if that office view is getting bleak and the Slack messages are getting mundane, it might be time to look into a digital nomad company to help you get out of your rut.
This article originally appeared in the May issue of SUCCESS+ digital magazine. Photo by Rawpixel.com/Shutterstock.com