Unsettled Is Making It Possible For Families To Be Digital Nomads, Too

Just because you have kids shouldn’t mean you don’t get to participate in the office-free, world-traveling life.

Unsettled Is Making It Possible For Families To Be Digital Nomads, Too
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Unbound by location, remote work allows people to escape the rat race of crowded, expensive urban centers. The real appeal of living a life in select countries around the world is a shot at that ever-elusive work/life balance, as found in communities where lifestyles are slower, cheaper, friendlier, and overall healthier for family well-being. But just like avid travelers who later have children do not forget the glory days of life on remote beaches, those same remote workers can be shocked by the hurdles of taking young ones around the world with them. For a new startup called Unsettled, this disconnect has not gone unnoticed.


Unsettled is part of a new batch of companies that have started to cater to the international-traveling “digital nomad”–workers who aren’t tied to an office and want to travel the world while they complete projects from their laptops–by setting up international co-working retreats or allowing workers to easily lease apartments in cities around the world as they travel. But the digital nomads envisioned in these companies’ business models are often young, single, or otherwise unencumbered. Unsettled is doing something different: They’re now opening the doors to digital nomads who are parents, and their families.

The offerings are different. For a 25-year-old freelance designer, balancing surfing and work may be the primary objective; for a parent with two kids in tow, the motivation may be providing an educational experience for the kids, where international families come together to share the experience of working and living abroad together, while preserving a sense of exploration and adventure.

Cofounders Jonathan Kalan and Michael Youngblood, who are incubating Unsettled as part of TED’s inaugural residency program in New York City, first started debating the idea while on a sailing trip with a group of friends. The company not only caters to a standard global millennial profile you would imagine–a freelance creative who wants to explore new destinations in community with others–but Unsettled is actually extending the idea to parents and families, perhaps the last mile in the global nomadic co-working craze.

While on a week-long sailing trip with other entrepreneurs from around the world, Kalan and Youngblood realized there was nothing stopping them from staying on the road longer. They had their laptops and good company, and that was all they needed. While together the travelers were able to connect over deep conversations on work, career, relationships, values, goals, and life ambitions in ways that might not be possible while at home.

“What is it that meets our philosophy of life, a movement we could believe in, and an experience we could help curate?” Kalan says they asked themselves.

This forms the backbone of the company and is essentially what Unsettled is offering with the first of what they’re calling “work retreats”: 30 days in either Indonesia, Japan, New Zealand, or Cuba with like-minded folks who can get their work done and enjoy a sense of belonging while on the road. Unsettled takes care of all the logistics and the people taking part co-create the overall direction of the retreat (think activities and day trips).


Kalan and Youngblood embody the ethos that shapes their company–Youngblood was managing editor for MIT’s Innovations Journal in Cambridge, where he has spent extensive time thinking about the new economy, work/life balance, global social impact, and creative lifestyles. And Kalan, a self-declared “explorer,” spent his childhood traveling around the world with his parents, before becoming an international journalist himself and dabbling in startups in Silicon Valley.

And while there are numerous players in the digital nomad space–WeLive, Roam, Remote Year–Unsettled is more intentional about curating the experience. When getting 30 to 40 people to spend a month together in a foreign place, there has to be thought put in to the character, personality, skill-sets, and overall traits that make up the people of the group. And so Youngblood asks himself, “How can I create this extraordinary month for others without them noticing?”

One answer to that question is that there is essentially self-selection happening; the people who are drawn to Unsettled tend to share qualities in common: they’re curious, adventurous, going through a transition, and wanting to break out of a monotonous 9 to 5 routine. But Youngblood also makes sure to Skype one-on-one with every applicant at least once, and he looks for people who want to contribute to other people’s lives. “I want every person to be present–I tell people to wait until they literally feel a burning desire for this kind of experience.”

So where do parents and families fit in? Given the well-established fact that millennials are craving new models of work and family–and many are now parents themselves–what would international co-working look like for them? Or as Kalan puts it, “How do we create structures for life that support mobility?”

Unsettled’s idea to extend international co-working to families essentially came from demand. Youngblood says that about every 48 hours he receives an email from someone with kids who wants to join their retreats. Even amongst the other TED residents, there are parents who want to join and extend feedback to the startup on how to make the retreats family-friendly.


On a recent call with several parents looking to sign up for the first-ever Unsettled family work retreat, there was talk of baby carriers, cribs, babysitters, teachers, homeschooling, and other logistics, but what stood out was the desire for community, connection, and belonging. While working remotely is lonely and isolating enough, those new to parenthood also have to handle the transition to parenthood, and the stress and challenges that presents.

“I’m looking for a safe space, where I can travel, come and go, and come back to the same group of people,” says Alvaro, a tech entrepreneur and father of two originally from Spain but living in Switzerland.

“Parents of different aged kids have different needs, so it may make sense to organize trips according to children’s ages,” says Sarah, a leadership development entrepreneur and mom of three in New York City.

“The gear required to keep babies safe and sleeping can be overwhelming. I now understand why people go to all-inclusive resorts. There’s so much plastic crap to haul, it’s nice when someone helps you,” says Amie, a Los Angeles-based writer and mom of one. “We travel a lot and work from all over the world. Traveling with a kid is a whole new beast for us. Sharing that with other nomadic families, coming together as a community, it’s critical for us and our kid.”

And the fact that these questions are being put on the table by the potential participants themselves is all by design. Unsettled wants parents to take ownership of the community experience, while the company stays in the background taking care of logistics. Youngblood thinks that people often get as much joy from planning as they do from the actual experience. “I remember being seven years old and planning a trip with my dad, looking over the atlases and backroads.” For him that stands out as the most exciting part of that particular journey.

Beyond the logistics of cribs and babysitters, the question of educational opportunities stands out as an unexplored space for international co-working startup. If both parents can work from the road, it’s one of the only things standing in the way of entire families living the global nomadic lifestyle. So what would education look like on the road? Unschooling, homeschooling, shared lessons by participating parents, “field trips” to farms and factories, or online curricula?


Though they’re not yet parents themselves, Kalan and Youngblood hear “over and over again from parents that they want to continue their lifestyles” of spending time abroad and networking.

But it’s a problem they’re intent on solving, to make sure parenthood doesn’t mean an end to the travel, network, and experiences. “How do we build these experiences around families? We want to create shared experiences for the parents and also how they’re raising their children,” says Youngblood. “What we’re really doing is making community mobile,” says Kalan. “We don’t want to just get a bunch of people drinking beer around the pool,” adds Youngblood.

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All Photos (unless otherwise noted): Carol Peixoto via Unsettled

About the author

Jenara is an overseas reporter for Fast Company and a freelance writer/producer in Asia, regularly on CNNGo, and a graduate of Harvard and UC Berkeley.