My co-workers are amused by my lifestyle as a digital nomad. I frequently get asked where I am and where I’m off to next. Sometimes, I post pictures in our Fun Chat and answer people's questions about life on the road.
What always surprises me is how many people tell me they wish they could travel like I do. I often reply with:
“What’s stopping you? We have the same job!”
Some of my co-workers do have very good reasons.
Some have just started families; others still have kids in school. Some are taking care of older or disabled family members, and a few are creeping up on senior years and disabilities themselves. And, of course, there are some saddled with debt from student loans and medical care for chronic illnesses.
I know many traveling families who homeschool, and several of the RVers I know have disabilities or travel with someone who does. Still, not everyone is willing to sign up for that, and that’s totally understandable.
Outside of this, though, many of us are young and capable millennials or Gen Xers, free to roam as we please. We earn a similar income and share the same work restrictions—or lack thereof. Most of my co-workers are extremely well-traveled, and several speak second and third languages.
So, why am I the only one living on the road full-time when many others want to? Only they know the answer, but here’s what I’ve seen outside of work.
Money and remote work are often not enough.
A few weeks ago, someone posted on Threads that traveling required courage. Someone else asked whether Courage could buy plane tickets and pay for hotels. Others added that if they had more money, they would absolutely travel more.
However, my experience—in America, at least—is that I frequently run into other people who make the same amount as me or more, and they still prefer the safety of their homes.
Even when the boss says they can work from anywhere, they either get an apartment in the city or buy a house in the countryside. I see this all the time.
How risk-averse are you?
When I left Jamaica in 2015 to become a digital nomad, I had neither the money nor all the answers.
I had just quit my finance job, making about $4 per hour, and had $2,000 to my name. When I bought the RV and hit the road, I didn’t have all the answers there either—and I certainly don’t have all the answers for moving to Spain.
It took courage to take that first leap of faith with a Jamaican passport and third-world savings. Once you’ve done it a time or two, though, it gets easier. The leap to Spain is a much smaller leap—in my mind—than that first big one out of Jamaica.
Not everyone has the luxury of hundreds (or even tens) of thousands of dollars in savings, a job lined up overseas, or a First World income. Some of us have had to navigate international spaces with weak passports, devalued currencies, and pennies for pay.
So, if you’re waiting for things to be perfect to take that leap of faith, you could be waiting a long time. I’m certainly not telling you to be reckless. I’ve talked a lot about having backup plans, like in: Design Your Exit Strategy Before Hitting the Road.
Once you have that backup plan—or two—a well-calculated leap of faith can take you much further than waiting for the “right time.”
If you’re a paid subscriber, you’ll receive a follow-up post on taking calculated risks next week. I’ll talk about:
How I make my long-term travel plans (like having a specific move date for Spain since 2023!)
How I decide when a travel risk is worth taking (like when I bought my RV without ever even sleeping in one before)
How I stopped waiting for the right time to make a move (like the first time I moved to Mexico)
See you then!