Working on a windy day at Playa Colorado in Nicaragua in 2019.

How to Start a Career as a Location Independent Technologist

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Editorial note: I am using a lot of jargon in this—very, very long—post. This is intentional. Some are subtle hints, some will hopefully give an introduction to things you’ll be running across in contemporary IT work. Have fun with it!

When I finally committed to the notion of leading a full-time nomadic lifestyle, I completely underestimated the impact it would have on my social life. I’d been working as a part-time, location-independent consultant for almost two decades. Through a series of very bad decisions on my part in 2018, most of my close friends had distanced themselves or walked away from me altogether. What did I have to lose?

Not much, actually.

But making friends in your forties is challenging. It’s even harder when you’re consistently transient. So I did what anyone else would do—I turned to Facebook.

I stumbled on a handful of groups centered around things like vanlife, camping in your pickup truck, and being a “digital nomad”. It was a relief to find so many kindred folks from all over the world in one place, virtual or not. Not the same as meeting someone in person, but still a great start.

One of the recurring questions in all these groups is, “What type of work do you do?” There’s a lot of overlap, and “digital” type work certainly seems to be a common characteristic. But a lot of people are just figuring out to how get started and are looking for advice.

I offered some work-related advice in one of these groups and there was more of a response than I expected. After just a few seconds of banging out a comment, I realized that the answer wasn’t exactly Facebook comment material.

So, without further ado, here is my wholly incomplete and thoroughly biased guide to Starting a Career as a Location Independent Technologist.

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