Everyone wants to escape the cubicle. Thankfully, the centuries-old 9-to-5 model is beginning to lift, and innovation and technology are helping us take our talents beyond the conventional workplace. I’m a strong advocate for labor-force innovation, but with the blogosphere’s “glamorization” of the digital nomad, we have to wonder, is this little corner of the revolution all it’s cracked up to be?



My story, in brief: I left a job in management consulting in New York three years ago. Then I worked in a business development role for another two years, handling assignments in Africa, Asia, Latin America, and the Middle East. It was the polar opposite of my Fortune 500 days: hands-on, results-oriented, and entrepreneurial. On nights and weekends, I hustled on my writing, personal consulting, and travel business until I could make ends meet. Now that I’ve been a digital nomad for a full 12 months, I find myself wondering: Is this what I expected? And what have I really learned?



On the one hand, I love it. Traveling has always been the best investment I’ve made in myself, and being able to wake up everyday in a new place with a completely self-directed mission is a privilege. I’ve nurtured a true, blissful detachment from material things by living with less than 50kg of belongings for over three years now, and I’m living well on about $40 a day in the countries where I travel. I won’t live like this forever, but by pushing the limits to see just how little money and how few possessions I really need is a lifelong wisdom many people will intellectually explore but never practically experience.



Another boon is that if I continue on this path, I’ll never be someone with a long wish-list of things to do in life but “no time” for doing them. Hitchhiking through Laos? Motorbiking in India? Studying silent meditation? Moving to Berlin? Working on a farm in Hawaii? With my economic necessities sorted, I simply dream up what I want to do and go do it.

We can all do this, but most people marry themselves to rigid ideas about life, as if working non-stop from 21 to 65 were built into our DNA and charting a different course may cause self-implosion.

“Most people marry themselves to rigid ideas about life, as if working non-stop from 21 to 65 were built into our DNA and charting a different course may cause self-implosion.”

Even when I stop traveling full-time, I’ll never tell myself “I don’t have time” to do something. Leaving jobs, working for myself, and living on a bootstrap have taught me not to fear anything or anyone, and to experience the full spectrum of human freedom and intelligence.

On the other hand, as a digital nomad, I live alongside an alternate reality that most people the world over are a part of, and I often get a bitter taste of the trade-offs that come with being “different.” I sometimes experience pangs of what can only be classified as cubicle envy, watching swarms of well-dressed corporates running to get coffee together in downtown Singapore or New Delhi. Whether they’re chattering about exciting new ideas or how much they hate their jobs, their camaraderie is a visible aura — people who work together every day, see each other every day, and who feel part of something every day, for better or for worse.

Then I stroll back to my guesthouse in a hippie skirt and sandals and play with my own ideas, write my own articles, and work with my own clients. Work-wise, I miss belonging to something with a life of its own, working in a team, and receiving more feedback than just commentary from my editors or on social media.

If you think you’re “stuck in a cubicle,” I’d tell you to appreciate all the things you (probably) enjoy by belonging to something like that: close and consistent relationships, community, your clothes on hangers, familiar places, love that is physically present, easy conversations, family in a nearby time zone, and a steady income that still puts you in the top percentile of richest people on the planet.

If you think I’m full of contradiction, you’re right. Humans are universally polarized beings, simultaneously gentle and violent, generous and selfish, ambitious and lazy. And there’s two very distinct parts of me, as well: the self who thrives on adventure and independence, and the self who craves normalcy, community, tradition, and permanence.

The latter self realizes that there is a very raw and magnetic part of human nature that keeps us all more or less working together with a common, herd mentality. It’s the self that understands that people innately want to do what everyone else is doing. We want to be able to easily relate. We want to belong. And when we find ourselves on the outside, living life in a fashion that essentially separates us from the majority, we struggle. Or at least I do.

“It may take awhile for my true purpose to iron itself out, but the best way to avoid paralysis in the face of so much opportunity is to just keep experimenting.”

Mitigating that rivalry is my free spirit, which now sees some exciting middle ground. We don’t have to work for 45 years in an office and we don’t have to be completely uprooted — we can periodically clear out space for unconventional living by reinventing ourselves, changing careers, negotiating shorter work weeks or sabbaticals, quitting jobs, starting new businesses, traveling to unusual places, going back to school, asking for big asks, breaking our routines, and taking the time we tell ourselves we don’t have.

I don’t know how much longer I’ll stay on the road, but the most important thing is I’m watching my purpose evolve through action. I don’t sit around and wonder what it would be like to be a digital nomad, I’m giving it a go. And I won’t sit around and wonder what it would be like to be a lawyer or a therapist or a non-profit organizer, I’ll give those a go, too. It may take awhile for my true purpose to iron itself out, but the best way to avoid paralysis in the face of so much opportunity is to just keep experimenting. Everything is a process and everything can be an adventure.

Fellow nomads, it’s okay if we realize that this lifestyle may be good for a period of time but not as a permanent choice. We can embrace the satisfaction of working for ourselves and leverage our experiences to become advocates of more broad-based workplace innovation. We can help others who are passionately seeking a transition of their own, and we can be as vocal about the challenges of our choices as well as the “sexy” veneer that sells books and makes our blogs go viral.