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How to Travel and Work Remotely Using Your Tech Skills (S5E20)

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When it comes to digital nomad careers, the tech industry can be a goldmine. Since the most important equipment in these jobs are typically computer + internet, travel coder jobs may be a natural choice for someone who wants to travel and work remotely.

Dave TrabkaThat said, you don’t often meet people who’ve actually taken the plunge and hit the road. Dave Trabka is a great example of someone who did.

After spending part of his career in finance, Dave stopped to ask himself if this was really what he wanted to do with the rest of his life. He discovered a program called Remote Year, which reoriented a lot of his life and set him down the path he’s on today as a Full Stack Developer at Innovation Department in NYC.

In today’s episode, Dave joins us to talk about how to become a digital nomad and travel and work remotely.

Disclosure: I’m a proud affiliate for some of the resources mentioned in this article. If you buy a product through my links on this page, I may get a small commission for referring you. Thanks!


Dave’s Remote Year Reflections

Listen to the episode to hear Dave’s full story. Here’s the short version!

Exploring Opportunities

The first step to any big life decision is mental, and it was no different for Dave. “I came to a stopping point where I just kind of self-internalized and asked the question, is this what I want to do with the rest of my life? And it was a really quick answer that, no, it was not. So I decided to explore what other opportunities might be a good fit for me.”

exploring opportunities

From there, he started to take advantage of online resources like courses and bootcamps. “I started exploring software development and went down the path of self-learning. I used free online courses like freeCodeCamp and bought a couple Udemy courses, just learning the basics fundamental HTML, CSS, JavaScript, and found that was really clicking.”

“After a few months of toiling with the self-learning, I ended up deciding to go to a bootcamp. I really wanted to accelerate things, be in more of a community, and have the support of instructors. I wanted somebody to lay out some of these project ideas and help me build a portfolio. So in February of 2018, I applied and was accepted to Fullstack Academy of Code here in New York.”

Discovering Remote Year: What Is It?

“Fundamentally, Remote Year was started as a program that you would join with anywhere from 50 to 75 other people,” Dave explains. “You come in with a job that you can take remotely—Remote Year does not provide you with a job. You either negotiate with your employer to go remote, maybe you're a freelancer, so you kind of control your own destiny, things like that.”

Even though it doesn’t come with a built-in job, using a program like this has several advantages. “Remote Year provides infrastructure and logistical planning to allow you to live in any given country for a month at a time, with an apartment, access to a coworking space, events in the different cities, and local connections to help out.”


Once you’ve finished a program (currently they offer 4 or 12 months), you become a “citizen” of Remote Year. Dave explains, “The big benefit of being a citizen is that you can basically drop into any other program. You could join an entire program, or you could drop in for a month. When I was in Cape Town in March, I just dropped in on another program and had access to 30 other people that were all doing the same thing. It makes it easy to jump into that community, make new friends, and have people grinding with you late at night in the office.”

Advice for a Remote Year

First of all, Dave advises, “Ease into it. There are easy ways to see whether this lifestyle might work for you. You don't have to commit to a full year right away. Maybe you just request a remote day or week from your employer here and there and go work from a random coffee shop. See how hard it is to interact with your team and get your job done as kind of a trial run.”


The other important thing to know? “Be ready for the roller coaster. Don't expect it to be sunshine and daisies. I lost a passport, we had two guys get dengue fever in Thailand, people lost family members and didn't have the cash to fly home to attend the funeral. We had one poor girl who had a freelance client who just never sent the check. So she ended up having to drop out of the program, because this expected income stream just never came in.”

You won’t usually see these difficult parts of being a digital nomad on Instagram, but the takeaway is that you should always have a backup plan. If you’re a freelancer, it’s best if you have multiple clients so you’re not reliant on one. If you’re working a remote job, think about what you’d do if a layoff happened. Either way, have a financial buffer to protect you from any emergencies that arise. It’ll take away that potential stress so you can focus on enjoying your time exploring a new country.

Links and mentions from the episode:

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