Jetfarers at Large #6: Ryan Singel on the Anatomy of a Moment

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Our Jetfarers at Large family is starting to expand, and we couldn’t be more excited. We met Ryan through one of our other Jetfarers, Cybil (you might remember her from this early interview), and spoke with him over a Google Hangout on a Sunday evening. After the interview, we were so inspired by his journey from rural Virginia to New York City and beyond. Today, he discusses how his upbringing has shaped his worldview, how travel helps him manage his day-to-day obstacles, and why he doesn’t believe in having a favorite place. I’ll let Ryan take it from here!

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JF: What is your 3-minute autobiography?

RS: I grew up in Charlottesville, Virginia and spent my childhood on a farm about 30 minutes north of the city. Growing up, I had a very nuclear upbringing – I had three older siblings (an older brother and two older sisters), my dad worked in the medical system and my mom was an art teacher. The theme of my childhood was basically outdoor play. We spent a lot of time playing in the rivers, riding our horse​s, going on long bike rides on the dirt road we lived on… you get it. It was really me and my siblings, together growing up – I didn’t really have the “suburban, cul-de-sac” experience. It has really shaped my opinions on the environment, what it means to be a community, how to help your neighbors, etc.

Now, working in the consulting world, I’ve realized few people have, literally, come from a dirt road.

My father was probably the most formative person in my childhood. He was (and still is) a really mission-oriented man who taught me how to work hard and finish a mission really early on. When I was 6 years old, I was making brush fires and chopping trees and building fences, and my father really did engender service and teamwork from his children.

In addition to that skills development,  he(and my Mom) also were really big about taking us on multi-week long  summer car-trips across the United States and Canada — to places like Yellowstone, Devil’s Tower, Banff, The Grand Canyon, Great Sand Dunes. We spent a lot of time driving, camping, and eating open-faced sandwiches in a tent. It was great, and formative. I honestly don’t know how my parents did it with four young kids, but they made the commitment to show their kids the world as best as they could. 

For college, I went to UVA where I majored in Economics, Foreign Affairs, and Public Policy. During that time, I did a few internships in the government, then finally went into consulting in New York, where I’ve been for about three and a half years. I haven’t really decided whether it’s for me yet.

came to New York primarily to get the other side of the story from my upbringing. It has been one of the most “out of my comfort zone” experiences I’ve ever had. Whenever I go back home, it reinforces how much this has changed my way of thinking and how I tackle problems.

JF: What has been one of the most difficult obstacles you’ve had to overcome in your life?

RS: I was really blessed to have had a really bucolic upbringing with a wonderful family and good friends. But through all of that, I’ve had a pretty hard time with mental health issues. Even now, it continues​. It had been really defining for me as an individual, learning how to cope with those issues and ensuring they do not undermine my goals. 

​Looking back, although it was great, I think in a way because I grew up where I did, I’m not sure if everything socially “clicked” for me, in terms of being able to form emotional connections. I’ve always seen myself as a little bit of an outsider. 
That’s part of the reason why I love traveling, you know? It’s a way to break out of the existential crisis and think about what character you’re going to be in your own life. You can set up a temporary shell in your solo travel experience to show the world and escape a little bit.
My recent trip to New Zealand was kind of an “Eat, Pray Love” moment for me. Back in November, I felt like I needed time away. I was either going to go crazy or I just have to cut and run. The trip gave me a chance to evaluate my mental health issues, whether or not I liked my lifestyle, whether or not I wanted to leave New York… It helped me reset.
This was definitely my biggest obstacle and it continues to be. I don’t know if it will ever be fixed, it’s just the way I am.

JF: In that moment late last year when you decided to reevaluate your situation, what did it feel like?

RS: You often hear, for the people who are making certain life choices, it’s literally their escape. There’s no alternative for them. It’s hard to understand that, but I think you can get to that kind of mentality when you reach a really tough point. Whether you hate your job, or your living situation, or you’re deeply unsatisfied for whatever reason, you can reach that point where you say, “I have to step away and figure out whether this is for me.”

One of the things that has helped me is coming to the realization that, if I truly needed to, I could quit my job by Friday and be on a beach in India in two weeks. [laughs] There’s nothing stopping me from doing that – I have the money, the time, the wherewithal, the independence… It’s easy to choose to quit for a bit, go do something else, then tackle something in a year when I feel better. Just knowing I could do that made me feel a lot better.


JF: Describe one of your favorite places in the world.

RS: I don’t really believe in the idea of a favorite place. The reason? Because I think the “favorite place” experience is a nexus of a lot of different things: the season, whether you’re solo or with others, the timing, the warmth, the wind, the color of the sun… I’m not a religious person at all, but there were one or two times I’ve felt “closest to God,” or a moment of “this is it, Ryan​” which I would characterize as a “favorite place.”

​About a mile from my parents’ house in Virginia, there’s a hill with a hay field. In the spring it gets this long grass that has a golden color. One time, about five years ago,​ I was riding my horse and we turned and ran up this hill. It was about 6 PM and it was slightly windy; the sun was just about to set and it cast a beautiful golden color. I just remember reaching the top of the hill and turning around and seeing the wind blowing through the grass, with the Blue Ridge Mountains in the background. The temperature was that perfect warmth where you can’t really feel the air. It was perfect and peaceful and quiet… no one around. I still remember exactly how I felt in that moment and how peaceful it was.

I can go back there now, and it’s still really nice, but it doesn’t have that same “holiness” like that day.

JF: How do you think traveling has transformed the way you think and live?

RS: There are four main ways traveling has​ changed my life, ranging from most serious to funny nuances. The one I think runs the deepest is that I use solo travel to think about my life back home. Going back to what we were talking about, I think travel has reminded me that success is not a defined thing, and the way you experience your life is unique to you. You are the protagonist, everyone is their protagonist. There’s nothing that says “you have to do something or experience something a certain way.” Especially living in New York, it’s insane the way that people judge each other.

The second thing is that traveling just reminds me that I can be happy with the small experiences. My satisfaction doesn’t have to be a grand scheme of what my Wikipedia page will one day look like. One of my fondest memories of New Zealand was, after a 6 hour hike, eating a wheel of brie at the top of a mountain. The amount of satisfaction I got out of that little wheel of brie was unbelievable!

Third, I’ve started to live more minimally. I don’t get much satisfaction out of material goods. I have a nice bed, I’ll admit that, but I won’t be buying fancy watches or an expensive car, EVER. I’d rather spend that money on experiences, travel, or other people.

Lastly, travel has made me realize that I hate roller bags! I’m probably the one consultant that refuses to use a roller bag. [Laughs] I like to be able to carry everything because I can walk faste– and it also forces me to pack lighter.

JF: What’s something you think many people have on their minds but are afraid to say?

RS: I think, especially as I hit my mid 20s, we start to see the path of potential disappear. For example, in this past Olympics, I realized most of the gold medalists were younger than me! [Laughs] I thought to myself, “man…what might have been.”  And it’s frightening! And it makes you question whether you’ve made the right choices, or if you’re on a different trajectory than where you should be. You really start to see the differences between how other people look at your decisions, like where you went to school or where you chose to work.

It’s like…that one decision I made in high school really affected the rest of my life. Things like if I had run faster, or did something better, or said “yes” to a certain opportunity. It can get overwhelming, dwelling on those “what if’s.” I think the implications of that is that you can get complacent, saying, “I have something good now and I don’t want to screw it up.” Tons of people have gotten over this, like crazy startup founders, but many people I know have not. In my friend group, there’s a lot of talk of wanting to do something different, but being scared of the risk.

JF: What do you think is the remedy for that complacency?

RS: You have to come to an agreement with yourself. Growing up, I always wondered how people end up living in a cul-de-sac with their families and have the same jobs for 25 years, kind of disappearing into the mass of stereotype, instead of being an insane go-getter. I think you have to agree with yourself on what kind of character you’re going to be. Are you okay with not hitting the benchmarks you’re supposed to hit? Are you okay with getting married later? These decisions need to come from a lot of introspection and admitting to yourself what kind of person you are. For me, I know I’m not a born leader. I was the youngest of four, and I was groomed to be a really good team player and a follower. It’s hard for me to be the guy who is going to change the world, and it’s something I’ve come to grips with. For a lot of people, you just have to have a really frank conversation with yourself.

I don’t have it figured out, but I’m definitely trying to think about it.

JF: What’s the best advice you ever received? From whom?

RS: I have two things, from cheesy quotes really. The first is to think about the solution instead of the problem. There’s no point in wasting time or energy worrying about why something happened or how hard something will be. It’s much more progressive to immediately pivot and solve it. I used to be a problem warrior, and there was a pivotal moment when I realized worries are prayers to my fears. There’s no point in worrying – instead I just find a solution and do it.This is why I like to travel solo, because you can fix problems on your ownand the only person you need to convince to roll with the punches is yourself.

The other advice I really liked is, “the only way out is through.” There are times in our lives when we’re up against a hard time, and sometimes all it takes is the mentality of just getting through it. That’s something that has been really interesting to think about. It makes you okay with struggle and doubt and failure, and it really makes life different. When you can turn your life into this underdog story, both you and other people will find it more interesting.

JF: What legacy do you hope to leave behind one day?

RS: I don’t really know. And I think I’m comfortable with that. I’m a big proponent that humans are a species, a creature. We’re here for a micro speck of time and place. I could get really rich and put my name on a building or have kids and have my legacy live on through them…but those aren’t really tangible to me. I don’t see it as a fruitful exercise to think about it, at least not yet. I just want to take some good photos, eat some good cheese, maybe drink some wine, light some campfires, and that’s about it!

Special thanks to Ryan Singel for sharing his story with us today! For more of Ryan’s adventures (and incredible travel photos), you can check out his Instagram.

If you’d like to see some of the other interviews and guest posts in our Jetfarers at Large series, check out the compelling stories on our Voices page.

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Kay is a full-time working professional located in Washington DC who takes every spare vacation day to get outside and explore the world. When she travels, she loves visiting the most iconic and naturally beautiful destinations in the USA and abroad. You can typically find her wandering the streets of a city, running through a park, taking ridiculous self portraits, or hiking a mountain somewhere. Connect with Kay: Facebook | Instagram | Twitter

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