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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Contemplating life at Playa Amarillo.

Letting Go Of Home

“All conditioned things are impermanent. When one sees this with wisdom, one turns away from suffering.” — Buddha

Simple as the Buddha may have made it sound, getting right with impermanence isn’t so easy. Accepting the true, transient nature of life means accepting loss at its grandest scale. Acknowledging that the most basal of our pursuits—comfort, happiness, love, life itself—have no final destination is a serious dose of reality.

It’s easy to interpret this nihilistically, particularly in the face adversity or grief. But impermanence doesn’t mean that these aren’t worthwhile pursuits. Life has meaning if you choose to give it meaning, whatever that meaning might be. And I believe that this is what the Buddha meant when he talked about impermanence—when you accept that the journey is what matters and begin truly living in the present, the bumps along the road are less painful because you’re not focused on them.

This is something that I’ve personally struggled with. I’ve experienced—and caused—a profound amount of pain and loss over the years, and viewing that solely through the lens of change has been nearly impossible. At some subconscious level, a big part of my decision to pick up and leave my old life is probably a feeble attempt to own that pain.

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Me at the summit of Springer Mountain

Becoming a Nomad – The First Ninety Days

“The hardest thing in the world is to simplify your life. It’s so easy to make it complex. What’s important is leading an examined life.” — Yvon Chouinard, Founder of Patagonia — 180 South

Today marks ninety days since I made the decision to get rid of almost everything and embrace a nomadic lifestyle. It’s been an enlightening experience to say the least. Mostly in that–after more than two decades of intense focus on business and unchecked consumption–picking up and leaving it all behind has been a lot of work.

Here’s what I’ve learned so far.

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A dozen homemade biscuits in a box.

Eating Healthy on the Road

Crossfitters are fond of saying, “you can’t exercise your way out of a bad diet.” Regardless of what you might think about Crossfit, they’re right. Sure, you can work out enough to justify an absurd number of calories, but this still doesn’t make all those donuts you ate on the way to work healthy. In fact, all that sugar is probably wreaking havoc on your training. Not to mention your pancreas, brain, adrenals, abdominals, genitals, and wallet.

Intrepid travelers already know how tough it can be to eat healthy on the go. Air travel and hotels are like a black hole, junk food supergravity drawing you slowly into a singular abyss. Traveling light and border crossings make carrying food a logistical challenge, sometimes impossibility. Pair that with the lack of cooking options in most hotels, and it’s easy to go completely rogue. Even a cheapo butane camp stove and a styrofoam cooler are big luxuries when all you have is a motel-grade Keurig and a microwave.

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A bunch of sticky notes on a wall around a sign asking about thankfullness.

Why I Became a Nomad

About six months ago, I started renovating my house in Atlanta. Groundbreaking was the culmination of years of daydreaming about becoming a fat-cat real-estate investor, and I’d spent the previous six months or so doing legitimate research and running the numbers. I had a high level of confidence that–once up and running–my quaint new AirBNB would generate just enough revenue to allow me to finally cut the cord and hit the road nearly full-time. All I needed was about $75,000 and another six months to finish all the work.

Problem. I didn’t have $75,000, and my credit score–while not completely in the toilet–was low enough to invite more than a casual chuckle from bankers. During the ensuing six months I would most certainly die from starvation, since my recent year of “soul searching” hadn’t been paying very well and I’d blown through most of my savings. So, naturally, I did what any other rational person would do–I got out the wrecking bar and started tearing down the walls of my 100 year old kitchen. What could possibly go wrong?

Quite a lot, it turns out.

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