digital nomad

Digital Nomad Series: The Paradox of Choice

If you haven’t seen Barry Schwartz’s TED talk on the Paradox of Choice, well, I recommend it. I also feel like I’m living it these days — when the world is your oyster, where do you even begin?

Coffee in Portland - Digital Nomad Series

A portrait of Portland coffee shops.

Schwartz talks about the conundrum of having too many options. How, when we have 24 bottles of olive oil to choose from, it actually makes the decision more difficult and makes it more likely we’ll be dissatisfied with our choices. (Seriously, go watch the video if you haven’t).

Last year, when I was confronting the prospect of quitting my stable, rewarding, reasonably well-paying job as a college professor, it was both liberating and terrifying. If I decided to cut the cord and go out on my own, what would that look like? What would I do? Where would I go?

I knew I wanted out of South Carolina. That was the prime motivating force behind my decision to resign. I spent three years in SC, and really, two was long enough to get clear that it wasn’t a good fit. As a liberal, spiritual but not religious, tattooed, sober single lady in her mid-30s, living in a relatively small town The South was not working for me. My job was awesome, but the rest of my life took a whole lot of work just to maintain mediocrity. And that’s not how I want to live my life.

So. I decided to quit my job. There’s more to it than that, but that’s a whole other post (or series). As I finished out the semester, I worked three jobs in order to build up my I-quit-my-job fund enough to stave off the panic. Over the next six months, I built enough business as a freelance copywriter/ghost writer/editor/wordsmith to dissipate the fear of starving or going without insurance (even if all I have is basic/catastrophic insurance at present). I built up six months’ savings in the bank and enough regular clients to feel like I was actually capable of making this work.

Thus, I found myself in a position to leave South Carolina and work remotely. I could go anywhere! Do anything! World = oyster, etc. Except. Then what?

Setting aside the legitimate budgetary constraints (freelance writing is great, but it doesn’t exactly rain cash monies), I found myself in a position to do, basically, whatever the hell I wanted. So, what did I want?

First, I wanted to figure out where I was going to move at the end of all this. I grew up in Las Vegas, and that’s definitely not on the list. I went to grad school in Austin, and I love Austin. But Austin is so. freakin. hot. And I’m real tired of the heat. So, I was back to square one in terms of finding a new place to live. Blank slate.

Digital Nomad Series Seattle Self Portrait

Got to spend a lovely day in Seattle after the Lake Sammamish Half

I went through a whole process of figuring out what I was looking for in a city, and I’ll probably write another post about that later. The point is, I hadn’t really anticipated how daunting it would be to have this degree of freedom of choice — both in terms of where to eventually move and also where to go while I’m doing this digital nomad thing.

Being able to go anywhere is awesome, don’t get me wrong — I’m very aware of the privilege inherent in my situation — but it’s also super overwhelming at times. Admittedly, I didn’t do a ton of digital nomad research before embarking on this adventure, but I definitely didn’t come across any warnings about the occasionally emotionally crippling force of this kind of freedom.

Four months into digital nomading, it makes a lot more sense to me why so many companies have popped up to create curated remote work experiences for people. I have an acquaintance who embarked on a Remote Year 18 or 20 months ago, and that’s kind of where I got this idea in the first place. 12 months of international travel, spending a month in each city? It sounded totally amazing… in theory. But after looking into enough of those kinds of programs, I knew that I wouldn’t want to sign up for one. I’m not good at (big) group travel. And I was (still am) nervous about making my freelancing work across very many time zones. I’m sensitive to my environment and living with strangers in strange places sounded like a recipe for being stressed out.

Consequently, I’ve been making my own itinerary — bouncing around the U.S. for about 18 weeks now, with only a loose sketch of a plan. I spent January in Pittsburgh, test driving the city as a potential new hometown. Then I returned west to spend a little over a month in Portland, and yesterday I drove to Boise to visit a friend and dog sit.

It helps to have an organizing principle, even if it’s an arbitrary one. Running half marathons has ended up as the de facto through line to help me make decisions about where to go. That, and who can I visit/crash with for a while.

In a few more weeks, I’m going to drive east again — making another lap around the US, chasing half marathons in Nebraska, Pennsylvania, and probably Wisconsin. And visiting friends up north now that things are thawing out. It’s exhilarating to be able to say, “yeah! Why not drive from Las Vegas to Toronto?” And/but, I often feel more than a little aimless.

I won’t say that I wish I’d planned this out better, because the degree of flexibility in my life right now is pretty amazing. But it’s also been really hard for me as someone who very much likes to plan. I’m a planner, y’all. I book airfare and hotels six months in advance. I have a color-coded google calendar that in my normal life — or, in what used to be my normal life — would make most people’s eyes bug out. But not now. Now it’s a vast canvas of blank spaces.

Leaning into the things that make us uncomfortable is a direct path to growth. And this has definitely been a growing experience. I’m looking at heading to South America this summer, which will be a whole new level of growth (including finally learning more than just a few phrases of Spanish). In the meantime, I’m excited to see what lies on the road (trip) ahead, even if it means periodic freak outs about what the heck I’m gonna do or where I’m gonna go this week/month/year.

Snow shoeing on Mt Hood - digital nomad series

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