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One Software Engineer Reveals What It's *Really* Like to Be A Digital Nomad

Posted by Amy Elisa Jackson

Last Updated April 10, 2017

It’s often talked about but rarely done: living as a true digital nomad, using the freedom of a remote job to travel nonstop, no official “home base” to speak of.

Whimsical and exciting? Sure. But not necessarily easy, and not for everyone. We spoke with Casey Flynn, senior full stack software engineer at InVision—a fully remote SaaS company of nearly 300 employees—about his life as a digital nomad.

How did you decide to become a digital nomad?
Casey Flynn: Back in March 2016, I had been living in San Francisco for a couple of years and I was ready for a role change. During my search, I came across InVision, and because the entire company is remote, that opened up the possibility of living anywhere.

Prior to discovering InVision, I had not thought about becoming a digital nomad. The next thing I know, I’m in Colombia, working at a Starbucks with my new engineering team at InVision.

How’d you make the transition to the life of a digital nomad?
Casey Flynn: You know that scene in Fight Club where Edward Norton blows up his condo and incinerates all of his stuff? That’s basically what I did. Only instead of a literal explosion, I just gave away everything I owned to my friends.
When the dust from that had settled, I was left with two suitcases full of all my physical possessions.

Since then, I’ve lived in a different country every month for the past year. Colombia, Germany, Singapore, England, France, Spain, Hong Kong, Japan, Korea, and more.

I usually rent an Airbnb for about a month to get the long term rental rate discount. I’ve developed an ability to very rapidly become comfortable with constantly being in new and very different environments. The variance in my daily workplace and “commute” is something I enjoy very much and helps me work better.

Do you work from a plan, or do you travel spontaneously?
Casey Flynn: I usually decide where I’m going next on a total whim, about a week or two in advance. In fact, I’ve had to smooth talk my way past immigration officials at certain borders who were very concerned about me lacking an exit flight when I entered a country.


What influences your choice to go to particular places?
Casey Flynn: My next destination is usually heavily influenced by casual invitations from friends that happen to live in certain places. There have been several occasions in the past year where I’ve decided in less than 5 minutes to move from one side of the planet to the other.

What logistical and planning tips do you have for creating a successful experience?
Casey Flynn: Show up at the airport on time. Other than that I would say it’s simple, more than you might expect. Just book a flight and get an Airbnb. Pro Tip: Get T-Mobile. T-Mobile’s network isn’t great in the United States, but internationally it’s amazing. Your cell phone magically just works almost everywhere you go.

What about your work and role at InVision makes being a digital nomad not just doable, but easy?
Casey Flynn: Naturally, our remote nature makes this possible and easy. I split my work day into multiple parts. Usually, I’ll spend half my day working alone, which is great for focusing. The other half is spent in contact with my team. It’s a great balance. There are advantages to being in different time zone—handing a 2 a.m. EST incident isn’t so unpleasant to deal with if you’re in Singapore and you just finished lunch!

What work challenges have you faced? Cultural ones?
Casey Flynn: Well, for one, when I left Colombia and went to Germany I kept saying “Gracias” to everyone that held a door open for me! Culturally, I think I’ve developed effective techniques for pantomime-based communication to get food at restaurants where I can’t speak the local language.

I switch back and forth so often between countries that drive on the left and the right side of the road, so sometimes I’m not sure which way to look when crossing the street.

Kidding aside—none of these “challenges” have really bothered me in the slightest. I think being a naturally easy going person helps a lot with living this lifestyle.

What’s different about working in a location versus visiting that place as a traveler or vacationer?
Casey Flynn: When you’re in a place for weeks to a month, you really begin to settle in and develop an intuitive feeling for what life is like in that location.

You are also likely going to have “normal” days where you casually go about exploring and living, whereas if you’re just a visitor in a new location you may try to maximize your time by packing in as many activities into the available time you have.

What do you wish you’d have known before you began your journey?
Casey Flynn: Honestly—nothing really. The experience and the discovery have been amazing. I feel if I had any sort of advance deep, detailed knowledge of how this lifestyle could be, it would have altered my experience.

What discoveries about living and working as a digital nomad have come as a surprise to you?
Casey Flynn: Through my travels, I’ve become more convinced that people everywhere are mostly similar. When we talk about people from different places, we may focus on the cultural differences between ourselves and those people. Focusing on those differences may lead us to feel as if we’re more different than we are similar. However, I think the opposite is far more true.

What’s next?
Casey Flynn: After a year of nearly constant traveling I’ve decided to try something new. I signed up for a Mandarin education program in Taipei, Taiwan. I will be studying Chinese in my spare time while progressing my career and skills as an engineer. My current plan is to spend at least one year in Taipei.

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