"So, here's the thing: I never planned to be a digital nomad. Hell, I don't even like the term. It always struck me as a self-important title that someone invented to make their cute little life situation sound even more impressive. (Same goes for the term "Thought Leader.")
I've never had the opportunity to really travel, and definitely not in the way offered by Remote Year. My travel experience up until this was a handful of business-related trips around Canada and America -- the usual cities, at the usual conference centres for the usual extended weekend. I went to Rome for a week last year with my family, and it was lovely, in that travelling-with-your-Mom-so-you-can't-really-party-or-drink type of way. Money was tight growing up, so we didn't have trips to Aspen or summers at the cottage. The idea of travel was a nice idea to me, like winning the lottery is a nice idea. It's something that happens to other people, or it's the subject of a mid-range Hollywood comedy. Between student debts and pursuing a career that wouldn't give me Scrooge McDuckian piles of money (hello journalism!), I had written it off as a possibility.
I didn't even apply to Remote Year. That honour goes to my best friend Jess, who, while applying for herself, called me up and said she found this program that could work for me. She said that, since I work for a website and work from home a lot, I could probably convince them to let me go full remote for a year. I was extremely busy that day, so I kind of nodded and said "Sounds great, Jess. Good luck." And went back to creating sponsored content for McDonalds or something. Jess, in her infinite wisdom, filled out the initial application form in my name, with my email and LinkedIn account. She told me what she did later that day. 
But then I made it to the second round, and started to take this whole thing seriously. And that's how I ended up typing this email in Buenos Aires. 
And for the record: Jess got in too, and we're actually travelling together in the same group. Because how horrible would it be for the guy who couldn't be bothered to apply to get in, and she didn't? 

But the one thing Jess was wrong about -- and the one area I severely underestimated -- was how willing my employer would be to let me do this. To put it simply, the majority of employers are not in a mental or cultural space to allow one of their own to go all Indiana Jones for a year on the company dime. It requires resources, trust, and a flexible way of viewing "employment" that I believe North American culture doesn't have yet, and maybe never will. I have friends who work in factories -- there's no way to go remote on that. Even my previous position, as the head of Sponsored Content, was considered too client-facing and vital to the health of my department for me to be abroad for a full year across time zones.
For me to pull this off, I essentially had to leave my position and take up a new one in the company with less client-based responsibilities. It was a lateral move, if not a demotion, and I literally made myself less vital to the company as a whole. I balanced the derailing of my former career path against the prospect of increasing my travel experience by several magnitudes within a year, and decided the latter was more important to me. It's a personal decision, and not everyone will be able to make the call I did. Also, my bosses need to be praised for essentially working with me asking to leave, then asking to switch positions and leave, within a two week period and believing in me enough to give me the all-clear. Not everyone will have this. It's important to remember how much of a privilege-upon-a-privilege this whole thing can be. It'll keep you balanced against the moments where you get drunk and sing "Who Wants To Live Forever" in the streets of South America, because you feel like a handsome, immortal prince. 
(NOTE: I may have done this.)

I'm coming up on the end of my fourth month, and I don't believe the reality of my situation has hit me yet. Before I packed my bags and left Canada I was living in a scenic little apartment known as "My Mom's Basement." The landlord was really nice (we go way back, and she gave me a reasonable price on rent), but privacy was an issue -- I didn't have a bedroom door, or anything to really block the sights and sounds of a relatively healthy man in his late 20s from the rest of his family. Every day on Remote Year, I'm not just learning how to travel for the first time, I'm learning how to live alone, how to balance my wants and needs, and how to enjoy a room with a door (and a lock!) for the first time in a long time. 
I thought that travel was for someone who didn't look like me, who didn't have my background, who had money to fall back on. And let's be real: That's still true. A non-trivial amount of people in RY will probably be okay, at least for a few months, if their work funding falls through. But this is a game changer. You don't have to choose between advancing your career or seeing the world. You don't have to feel like a complete chump for focusing on debt repayment and career advancement while your Friend With The Startup keeps posting rainforest selfies and Rumi quotes. I realized in those final two weeks, when I had to convince everyone in charge of my fate to let me do this, how much I was willing to fight for this opportunity. To become that douchebag with the rainforest selfies. 
I made some trades for this, both on a personal and professional level. We all have people and situations we leave behind. We hope they don't change too much in the interim. We hope we won't change to the point of being unrecognizable. We wonder if we'll even want to come back in a year. We wonder if we'll even have to. People in Remote Year refer to us being part of a social experiment, and that's extremely true. You'll deal with moments and combinations of emotions no one you know has ever had to grapple with. 
And I don't know about you, but I think that's fantastic. I had a life back home. It was good. I loved it and the people in it. This is weird, and new, and has fresh challenges every week. This entire year could end with me being the hottest of hot messes. But I'll have earned it, and I'll know I fought for the opportunity to be the hottest, weirdest mess in the world in pursuit of finding out if I could be more, if I could actually fight for the things I never thought I'd get to enjoy."

Mike Sholars is a Blogs Editor for The Huffington Post Canada and a participant on Cousteau, Remote Year's third cohort. 

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