Meet The Single Mothers Raising Their Children While Traveling

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By the age of 22, Cailee Nicole was living in Kansas City, Missouri, with a thriving career as a startup advisor. She owned her own house and had her own car — yet she still felt like something was off. “There was no reason for me to be feeling that I was anchored down at 22,” Cailee explained in a phone call. “I should be a little more free. I shouldn’t feel like I had passed my opportune years.”

She woke up one morning in October 2014 and decided that she wanted out of the Midwest. By the end of November, Cailee had sold her house and her car, and bought a one-way plane ticket out of the country. In January, she hopped on a 35-hour flight to Thailand — her first time ever leaving the United States — with no plans to come back. Given that her job was remote, she knew she’d still be able to support herself while traveling. “My plan, since I had sold everything, was to leave the country and travel indefinitely. I was going to travel the entire world.”

Cailee’s story is similar to that of many other twenty-first century nomads, who are privileged enough to leave corporate jobs and unfulfilling 9-to-5s to travel the world, building a startup along the way or relying on savings and freelance work to fund the journey. The location-independent lifestyle, almost by definition, requires a certain level of flexibility and a willingness to leave family and friends behind, so the stereotypical digital nomad is young, single, and often male.

The term “digital nomad” has been bouncing around the Internet for several years now. In essence, it refers to people with location-independent, technology-based jobs who make the conscious decision to take advantage of that freedom to travel the world, rather than stay in one spot — think coders or social media marketing managers.

But being a digital nomad is more than being a tourist who checks their work e-mail while visiting Venice for a couple of weeks. It requires a lifestyle shift, packing up all one’s belongings, saying good-bye to paying rent in one city, and hitting the road indefinitely, laptop and iPhone in hand. They are generally individuals who often “reject the idea of settling down,” as one self-proclaimed digital nomad Jay Meistrich explains in an essay published on Medium, “How I built a startup while traveling to 20 countries.” But what might be lost in stability is made up for in adventure and even productivity. Not only is Meistrich exploring cities from Bali to Budapest, he even argues that, as a digital nomad, he’s getting more work done and saving more money by traveling the world than he was staying put in San Francisco. “I can’t afford not to travel,” he writes.

The start of Cailee’s journey resembles those of her nomadic peers in many ways — from the desire to see the world to the ability to support herself remotely — but there is one notable difference. Instead of embarking on this adventure alone, she brought along a travel companion: her 2-year-old daughter Ellie.

Cailee, who has been a single mom as long as she’s been a mother, and Ellie spent six months in Southeast Asia, primarily in Thailand. Cailee documented the trip online, in a series of vlogs and Facebook posts. She’d received a lot of flak from family when she announced the decision to leave with her daughter in a YouTube video, but they ultimately changed their minds when they saw how much both Cailee and Ellie had grown.

Cailee returned to the United States in June 2015, in part to go on a cross-country road trip with a man she met online who is now her husband, but she continues to see the positive effect of that time abroad on her daughter. “When we started traveling and meeting new people, it helped Ellie blossom and open up,” gushed Cailee over the phone. “Traveling removed any fear that she may have had of the unknown. That was her first time in the ocean, her first time running through sand, her first time seeing something incredible like huge elephants.”

Lainie Liberti is another single mom who left her home and business in southern California with her son Miro, then eight, to travel in 2008. “Before we left, I knew instinctively that fifth grade would have nothing on a year of traveling,” she said during an interview over Skype from Playa Del Carmen, Mexico. The duo had originally planned to backpack around South America for a year, but after eight months on the road, they hit a turning point and, as she explained, “We just looked at each other and said, ‘Let’s not go home. Let’s figure out how to make this work.’”

Mother and son have since spent the last eight years as full-time travelers, proving by example that this lifestyle can be sustainable in a long-term sense.

The first step to achieving that sustainability was getting their finances in order, a struggle about which Lainie has been very open on her blog. “When we first started out, I had savings,” she explained. “Then that went away. Then I had to do consulting work and design work and maybe a few logos.” She found that freelance work unfulfilling, so she and Miro eventually started running retreats and summits for other traveling families through their company Project World School.

Given the lack of a safety net when traveling overseas, the stakes are high and there’s no room for failure — but as a single mom, ensuring financial stability abroad is not necessarily more challenging than it is in the United States. Crystal Blue has been traveling with her daughter River since February 2013 and writing about the experience on her blog The Enlightened Globetrekker. “My challenges were more so in the United States before we left, as I was pressured financially and time-wise,” she explained in an e-mail.

Like Lainie, Crystal also started her own business, an inspirational travel adventure company called Enlightened Globetrekker Adventures, and she finds that the freedom this lifestyle allows outweighs the frustration of not having a more concrete home base, especially when it comes to raising her daughter. “I didn’t believe in the values she was adopting from the culture [in the United States] and was constantly at odds with that internally and externally.”

This desire to raise kids as global citizens with a more holistic and compassionate value system is another huge appeal of the full-time nomadic lifestyle for some moms. Lainie, for one, has become an outspoken advocate for unschooling, a philosophy that dispenses with textbooks and curriculum in favor of student-directed experiences.

In the simplest sense, unschooling means, “There’s nothing he has to learn. Miro is all self-directed and self-guided,” she explained. If he wants to spend the day in bed and play video games, that’s his choice. But because he’s been empowered to make his own choices since he’s been ten years old, he makes some really damn good choices for himself.”

Lainie coined the phrase “world schooling” to include the benefits of traveling while employing this educational framework, and the experiences the duo have had in pursuit of learning beyond the classroom are definitely unique, from working on a farm to learn more about permaculture, ethnobotany, and organic farming, to wandering around Mayan and Incan ruins to discover ancient civilizations.

With Project World School, Lainie has, “developed a system that creates these beautiful learning communities that helps teens step out of their comfort zones, build partnerships with other people, and learn to look at the world through new lenses and try on different worldviews.” And though these in-person meet-ups are valuable to Miro’s education and ability to interact and communicate with others, the bulk of the community-building and networking takes place online.

None of the single moms I talked with necessarily identify as digital nomads, but they all conceded that the Internet is what makes this lifestyle possible. “We could not world school as effectively as we do without the Internet, without technology,” said Lainie. “It’s vital.”

The Internet is also how more single moms are finding out about this way of living, and the single moms who are already out there are providing inspiration for others who might be hesitant or afraid of the instability. “Everybody really is looking to veterans for guidance and support,” said Lainie. “And because I focus primarily on the education aspects through natural learning, there’s a lot of questions,” many of which she answers on a private Worldschoolers Facebook group she created and administers, which now has over 7,200 members who are all also interested in or living this untethered lifestyle.

Cailee agrees. “The number of mothers I had contacting me for advice, to have someone to talk to doing what they wanted to do. That was so rewarding. I haven’t posted any travel videos in a while but I’m still getting messages, and it’s a great validating feeling.”

As remote work continues to become the norm, more individuals and families will embark on these long-term adventures — and these single moms are proving that the lifestyle of a digital nomad can be accessible to populations beyond just single, Silicon Valley bros. “I think it’s for anyone who is in the position to do it and wants it,” said Lainie. “Learning how to have a healthy relationship with fear, your inspiration and instinct, and multiple steams of income and community, you can do it.”

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