How did this whole thing start for me? I’m really not sure. In 2008, I quit my full-time job to start freelancing, with some vague ideas about “travel” and “I could work from the beach.” Instead, I ended up working from Ann Arbor, Michigan, where I had enrolled in a PhD program so I wouldn’t starve to death when I had no clients.
The first winter in Michigan was rough, and in the summer of 2009 I jumped at the chance to go back to New York for a month and work on-site for one of my freelance clients. I crashed on friends’ couches, did a lot of Skype calls to convince my professors in Michigan that I was still “committed,” and realized that I really could work from anywhere.
The next year, my school work was all independent: writing a proposal for my dissertation. A yoga teacher I knew was having a week-long retreat in Mexico over Thanksgiving, and I decided I would go to that and then stay in Mexico for another week and work. This was my real first exploration into the life I’m now mastering. I rented a little house near the beach through vrbo (air bnb wasn’t even a thing yet!) that claimed to have wifi (I think it actually did, but I don’t remember angsting about the presence of wifi nearly as much as I do now). I did a couple of calls, wrote a lot, and thought I was THE SHIT.
When I got back to Michigan, I started reading about people like Chris Guillebeau and Tim Ferris (I actually just came across some notes I took during Chris’ “Working from the Road” webinar in 2011) and realized that I was neither the only nor the first person to envision a life like this. Learning that other people had been nomading, making money, and being happy made me even more certain that this was the right path for me. And so it began…