​Ryan and I first met when he joined We Roam (now WY_CO) in Morocco in April, but if I’m being honest, I really didn’t know what he did until I sat down to interview him in December. What I appreciated the most in talking to Ryan is how much he values the idea of following your interests. His story makes it clear that when he second-guessed himself and did what he thought he was supposed to, he wasn’t as fulfilled; but when he was attuned to what he found exciting, things started to fall into place. Our conversation has been edited for length and clarity.  
 
When you were 17, what did you want to be?
 
I thought I wanted to do something in engineering, probably mechanical engineering. Growing up, I was always building things, like train sets and that sort of thing. The train sets turned into going to Radio Shack all the time. That was like the toy store for me growing up. I would soup up my remote control cars, and one time I built a little robot out of a box with lights and little motors that I pulled out of my remote control cars.

I specifically saved Michelle Bird for my last interview of my year of travel, partly because she was the last person I saw before heading back to the US, and partly because there’s something really extraordinary about getting to interview one of the people I love most in the world. We really couldn’t have planned it better, as we ended up chatting on the steps of a cemetery on top of a hill in Lyttelton, New Zealand. Although I knew the broad swaths of Michelle’s story, I loved hearing the tiny details that eventually led to her sitting in that cemetery with me. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
After I stopped wanting to be a ballerina or a princess, I thought about being a veterinarian, but I really had absolutely no idea. I was the fourth of five kids, and the only girl. I got good grades and participated in all these sports and marching band and I was president of the French Club and I started a community service club. I also went through a prolonged grunge phase, featuring lots of flannels, hair down to my waist, and drawing the anarchy symbol on things.  With five children, my parents were extraordinarily proud of me, and very much like, “Whatever's happening, let's not mess it up.”

Sean Harvey is the co-founder and COO of We Roam, the remote work and travel company I just spent the last year adventuring with. Sean was my penultimate interview of the year, and we had a classic Bali experience, chatting over kombucha at an airy indoor-outdoor café with geckos skimming the walls. By the end of our conversation, I was profoundly grateful that when Sean learned about the idea of digital nomads, rather than just find a remote job himself, his instinct was to build a company like We Roam. Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
I wanted to be a professional soccer player. I was one of those kids who played every sport. I didn't grow until maybe the beginning of high school, so I was really small but really fast. So I played every single sport up through middle school, and in high school it switched and the focus was all on soccer.

Doug Tyler is the lead engineer in the digital marketing department for the Golden State Warriors, basically living the dream of every sports-obsessed guy I knew growing up here in the Bay Area. While tech is not an unusual field to work in in Northern California, Doug’s path to engineering is a bit unorthodox, starting with making movies with his younger brother in high school, and then being at the forefront of social media after college.  Our conversation has been edited for length and clarity.
 
When you were 17, what did you want to be?
 
I wanted to make movies. I wanted to be a director. When I was a really little kid, my parents would just sit me in front of this big screen projector we had. If the screen was on, I’d just sit there and watch it for three hours, and laugh at all the jokes, and get scared at all the scary parts. I always liked movies.