I Tried to Travel While Freelancing & Messed Up

This blog post was updated on July 22, 2021.

I hadn’t even boarded my flight to Copenhagen when I realized I may have gotten in over my head. My laptop was open on one of the scant metal tables, the kind you’re lucky to find in an airport terminal after 8 p.m. A $10 beer was on the tabletop next to the keyboard that was furiously typing away on as I tried to get the most out of the $8 I’d just paid to use the Wi-Fi.

My girlfriend sat across from me sipping a glass of red wine. “Babe,” she said, “do you really have to do work now?”

“I just need to submit a couple of posts,” I lied, looking at the eight pending assignments with my name on them in the blog queue, all of which were due the next morning. “It shouldn’t take that long.”

At the time, I was a veteran of the new and growing independent digital workforce. For over three years, I’d worked from home full-time for multiple clients. And as I became more and more comfortable with my role in the gig economy, I came to a series of epiphanies, one after the other, on the “freedom” I had. It started with “Oh, I can work from a coffee shop…or even a bar!” Soon it was “As long everything gets done on time, I can stay up to 3 a.m. and sleep ‘till noon.” And then eventually, the biggie: “What’s stopping me from doing this while traveling?”

It’s a tempting daydream for anyone who’s ever telecommuted or been paid via 1099 — foregoing a fixed address and opting to work on a computer while sitting at a cafe in [insert dream destination] instead of on a computer while sitting at home.

So I decided to go for it. Or more accurately give it a try. For over a month in the summer of 2014, I lived (and worked) out of my suitcase while exploring Scandinavia (thanks to some low-cost last minute flight deals). It was a minor jaunt compared to the professional freelancers who travel year-round and blog about it. I was sure I could pull it off.

I was wrong. And if you’re thinking of trying out the international digital nomad life, you can learn from my story.

Lesson #1: Get Ahead of Your Deadlines

In my excitement for the extended time abroad, I’d forgotten that the freedom of freelancing has a cost (deadlines) and greatly underestimated the time I’d have work on some assignments before leaving. Hence the bit of deadline drama at the airport.

I was rushing to do work before take off and I was rushing to do work after we landed. I would’ve rushed to do work on the plane, but it didn’t have Wi-Fi. When we finally got to the first stop on our journey, a beautiful seaside house, I left our hosts and my girlfriend waiting to formally welcome us with a champagne toast in their garden while I rushed to get online and send an email to a client.

“If I’d planned things out better, I could actually being enjoying this,” I thought as I climbed down the stone steps from the house to join the intimate celebration.

By just getting a few days ahead of my deadlines, I would have prevented a lot of stress and been far better equipped to handle the tiny calamities all travelers have to deal with.

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Lesson #2: Bring Your Own Internet

It seemed like a given in my Brooklyn neighborhood filled with Wi-Fi abundant cafes, but access to wireless Internet (the lifeblood of the 21st-century freelancer) isn’t exactly guaranteed when you’re traveling.

Within my first week abroad, it felt like I was in a constant struggle to find Wi-Fi. The lone cafe in a tiny fishing village along the Baltic Sea, where I camped out with my laptop for three mornings straight, was closed without warning on the fourth day (the owner felt like taking a day off) and I had to scramble to find somewhere else to answer emails and upload blog posts. I lost a whole afternoon and evening that I’d planned to work on while riding from Stockholm to Hässleholm because the train’s Internet service was out.

For any other traveler, these might have seemed like small annoyances, but for me they were incredibly frustrating. The time I’d scheduled to do work was wasted and I’d have to make it up out of my slated free time, which I was using to discover and get to know the places I was passing through.

The simple solution to such maddening and unpredictable issue? A 3G wireless hotspot device from an international carrier, so I really could work from anywhere. It may take a bit of research for you to find one to use while traveling through different regions, but many cellphone plans, like Google’s Fi and T-Mobile, are now offering flat-rate, international, unlimited data packages — so you can use that to turn your phone into a hotspot.

Lesson #3: You Have to Work

Traveling while freelancing was tough for me, even after I finally managed to get ahead of my deadlines and have reliable access to the Internet. It felt like the demands and needs of the job I’d mastered were dialed up to the max and the tasks I could easily bang out at home were monumental. I was having trouble finding motivation.

The hard truth about traveling while freelancing is that it isn’t a vacation…but it has all the trappings and feelings of one (you’re in a new place, meeting new people, etc). So the excitement to explore and take in an exotic locale directly clashes with the need to do your job.

I had to force myself to spend a whole afternoon working inside while a group that had invited me on a hike was out enjoying nature. I passed up on a night going out to bars so I could have a Skype call with a client. And more than once I stressed getting an assignment done while everyone around me was laughing and having a good time.

If I didn’t do those things, I wouldn’t have enough money to not only keep traveling but survive.

Lesson #4: You Can Still Enjoy the Trip!

I realized I couldn’t “vacation” while traveling as a freelancer, but I could manage to fit in all the vacation stuff in my free time. What a non-freelancer does across two full weeks off from their salary job, I could do in four weeks of mix-and-matched free time.

Freelancing is flexible work. I could spend a morning exploring Stockholm, if I used the afternoon to write and turn in projects. Or I could relax at the beach all day, as long as I dedicated the evening to answering emails and managing client requests. What’s more, even though I couldn’t visit museums or wander city streets during my work time, I was still immersed in another culture on another continent — enriching the experience even more.

When I finally got back home, I was exhausted. Not just from the last minute flight deals that took me eight hours back across the Atlantic and the jet lag, but from spending four weeks working AND visiting a foreign country. I was worn out getting the most out of my time, but also kind of troubled by the experience.

I had an opportunity to experience travel as a freelancer and realized it came with a price. It struck me that maybe full-time freelancing (especially while traveling) wasn’t as freeing as I had thought it was. I’m not the first to come to this conclusion and I’ve since traded in the freelancer life for a more “9-to-5” existence. But it was still worth the experience and if I’d had a better idea of what it cost to keep up my freelance work before I’d left, I’m sure I wouldn’t consider the attempt “disastrous.”

I still feel the occasional urge to give the digital nomadic life another try (maybe even for a longer). If I ever do, I’ll know how.