I grew up in a family that farmed. As farmers, my mom and dad worked together. It wasn’t always peaceful. There were plenty of problems, but my parents had a lot of freedom and flexibility in their lives overall. When I became an adult, it was my expectation that work should embody this kind of flexibility. In other words, I felt strongly that my work should support my family and my life, and not the other way around.
When John and I met back in 1995, I was working for a dry cleaning company, a job I’d chosen because the hours were conducive, overall, to my creative schedule. At the time, I was contemplating dropping out of school to start a band. I’d sit for hours in my apartment living room, fiddling with my guitar and working for a dry cleaning company was able to support that habit without interfering with it too much. That’s not to say that it didn’t irritate me to go into work at 3:00 in the afternoon. It did. But I was able to stick with it because it didn’t bring my creative pursuits to a grinding halt. It just interrupted them.
John’s family was disconnected. His mom was a teacher, his dad worked in food service. But John was a professional musician when I met him. Shortly after we moved in together, he was hired to play keyboards with a country band that toured the Midwest playing county fairs. By that time, I was working for a staffing agency that was willing to let me carry a beeper to do my work on the road. So John and I went together to county fairs from Arkansas to Minnesota and Colorado to Mississippi. And once we’d had a taste of this one-the-road, living-and-working-together lifestyle, we were totally hooked.
Those were the days before the Internet, before Facebook and the rise of the digital nomad. There were no such things as digital nomads back in those days. Cell phones were the size of a loaf of bread and weighed as much as an urban telephone book. But the world was changing quickly.
My daughter Lydian, now 17 years old, struggles to make sense of her place in the world. What should she do? She was homeschooled, or rather, “world schooled” in 30 different countries. Over the past 3 years, she completed her associate’s degree. As a 17 year old, she’s college-educated and she absolutely hates being tied to a schedule. Her teenage brain wants to find its niche; it’s reason-for-being, but I keep telling her that I’m still searching. My reason-for-being seems to be a moving target or a range of different things rather than one static item. When I was 17, the Internet was non-existent. I couldn’t have predicted my life path or my livelihood because the means through which I make my living didn’t exist at the time. I hedged my bets on medicine and aimed toward medical school. Now, I thank God that dream never materialized. Who could’ve guessed where our U.S. healthcare system would end up a mere 20 years later?
The digital nomad lifestyle seems, on Facebook, Twitter, or Instagram, to be idyllic. And it is in comparison with the traditional desk or office job. I mean, it’s ideal to me because I rate flexibility and freedom highly on my list of work-related values. But it isn’t easy. It’s my desire to have flexibility that motivates me to go ahead and deal with another client who’s sent me work with some extra-challenging (and previously unmentioned) specs attached. It’s my passion for freedom that motivates me to stay up until 2:00 AM writing for my blog or posting videos to YouTube in the hopes that my own work will someday take hold and support me. I work hard at the jobs that promise me flexibility and freedom and I shun the work that ties me down because I know that I can do the work of 3 people if I’m free to work when I want to. The second I’m tied to a schedule and a particular location, my options become limited. It’s harder for me to cast off on new ventures without some kind of major sacrifice (usually pertaining in the short-term, at least, to income and stability).
Becoming a digital nomad takes courage, but it also takes social support. People who work in traditional job setting don’t understand the challenge of self-motivation as a daily confrontation. Some people have trouble motivating themselves to complete projects, other people have trouble motivating themselves to enjoy their relaxation time when there are projects lined up, waiting to be completed. John and I suffer most from the latter problem. That self-motivation beast rides around on our backs. We restrain ourselves from working with great effort. People who work 8 to 5 don’t necessarily appreciate the subtleties of this type of problem.
John and I support each other and now that Lydian has graduated from college, we’ll support her as she takes her first leap into the Remote Work World. But for people who lack this kind of internal support-network within their own home, I have to say that the social support you need to do remote work shouldn’t be underestimated. Online clients are mean and shitty. In-person bosses who run businesses that take in modern nomads for temporary stints can be unpredictable. As someone who works short-term for clients or bosses, it’s necessary to size up employers or contractors quickly and make decisions that would be frowned upon in the in-person-brick-and-mortar world. This is where it can be incredibly helpful, if not essential to have a digital nomad community or something equivalent to it to help you see the forest for the trees.
The nomad lifestyle is desirable for a lot of reasons, but it’s a world away from office cubicles and work settings structured with a hierarchy of management and executives. Merely working as a digital nomad is culturally significant and unusual without even factoring the possibility of doing online work from another country that’s very different from your own. It takes time to acclimate to the rhythms and whims of clients, a diversity of different types of work, and all the technology that keeps changing and growing, glitching out, and wreaking havoc at times.
This article speaks in generalities about remote work because I have to meander my way into the details, having spoken rarely of what I do or what John does with the rest of the people who know me face-to-face. For normal people who think that it would be fun or relaxing to work remotely, I rarely present my case. I don’t work in my pajamas unless it’s at 3:00 AM and I’m finishing a project that’s really bothering me. And I don’t NOT work (another common thing that “friends” and “family” believe about me and John as digital nomads/freelancers). For readers who want to better understand what it’s like to work from anywhere and live the nomad lifestyle, my hope is that this series of articles is inspiring as well as realistic. There’s nothing better than having control over one’s work and one’s life. I love it and I don’t want to change it. But you have to be willing to take control of your work. Or it will take control of you. As with anything remote work offers certain advantages and certain disadvantages.
John Talks About His Remote Work (video)