How NOT to be a digital nomad

I learned the hard way with 5 mistakes you shouldn’t repeat

Grant G. Leonard
6 min readSep 28, 2022
Me in South Lake Tahoe watching a beautiful sunset

When I started my business at the age of 22, I had one overarching goal in mind: geographic autonomy. I figured that if I could achieve the autonomy to work where I want, then that means I would also have the freedom to choose when I worked and even what I worked on and who I worked with. To the dismay of my mother who always wanted me to stay in my hometown of DC (sorry, sending me on a semester abroad to Europe forever planted the movement seed), I decided to test out digital nomadism in 2019 just under 5 years into running my shop. Here’s what I did wrong:

I wasn’t thorough enough

Before moving anywhere, research and analysis are absolutely necessary. What’s the typical cost of living for someone in their late 20s? Does my dollar stretch as far there as it does in my current situation? Are there other digital nomads there? What kinds of professionals are in that community to network with, and what industries and subject matters do they represent? Is there even a professional network to mingle with at all? How affordable is housing? Is that housing sustainable for as long as I need it to be? What happens if I need to go to the doctor or the dentist, or if my car breaks down? Etc, etc.

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