A Conversation with Jedidiah Jenkins

The writer and Instagram aficionado considers what his Patagonian trek taught him and why he adores Elizabeth Gilbert.

jedidiah jenkins

On the eve of turning 30, terrified of being funneled into a life he didn’t choose, Jedidiah Jenkins quit his dream job and spent the next 16 months cycling from Oregon to Patagonia. Chronicling the trip on Instagram, his photos and profound reflections on life soon attracted hundreds of thousands of followers, garnering attention worldwide and features in National Geographic and The Paris Review.

In To Shake the Sleeping Self, his unflinchingly honest memoir, Jed narrates the adventure that started it all: the people and places he encountered on his way to the bottom of the world and the internal journey that prompted it. Grappling with questions of what it means to be an adult, his struggle to reconcile his sexual identity with his conservative Christian upbringing, and his belief in travel as a way to “wake us up” to life back home, his memoir is a soul-stirring read for the wanderer in all of us.

Recently, Jedidiah spoke with Read It Forward’s Jesse Aylen, alighting on the vitality of speaking truth no matter the cost, the pleasures of hand-drawn maps (and tattoos), and what he loves most about Instagram.

Read It Forward: Can you talk about the genesis of To Shake the Sleeping Self?

Jedidiah Jenkins: The book really came as the fruition of my 20s and figuring out what my skillset is. I went to undergrad thinking I was going to become a film director, and then to law school thinking I was going to become a human rights attorney. And as I was experiencing life, I kept being affirmed in my storytelling abilities.

But in my mind, writers are always in their 50s, living in Big Sur. I was in my late 20s and didn’t feel equipped; I felt like a schmuck trying to write a book in my 20s. I thought, “What would I have to tell people? Maybe if I do something objectively interesting, some wild trip, and then write about it as a travel writer, I can get my sea legs going and see if I’m any good at this.” At least the adventure will be interesting, if not my reflections on it.

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RIF: Right.

JJ: I met a guy who’d ridden his bike from New Jersey to Patagonia. The moment I heard him, I was like, “Oh, that’s exactly what I’m going to do.” It was about the pace of being on a bicycle, the way you see the world is so beautiful, and you can make it to Argentina or Chile in a year and a half. It’s this season of adventure, and then I’m going to write a book and see if the trip teaches me anything about where I’m at in my life.

RIF: You spoke about how biking would be faster than walking, obviously, and your parents actually walked across America, didn’t they?

JJ: They were made famous by walking across the country in the ’70s. It took about five years. America was really upset with itself about the Vietnam war, torn into pieces, and they set out to understand their own country. My dad met my mom on the trip, married her, and they walked from New Orleans to Oregon together. I grew up in a household where my parents had walked across America; they were on the cover of National Geographic, had written bestselling books. That really planted a seed of adventure and fearlessness in me because they had it. So, to honor them, I started my bike trip at the beach where they finished their walk. At the exact spot where they finished—I carried my bicycle to the ocean and then walked it out and began to ride.

RIF: Were there surprises along the way as you traveled? It was such uncharted territory for you.

JJ: I mean, I was definitely surprised by how much my ass hurt, the tailbone, and it hurt for two weeks. Like, to the point where I couldn’t really sit on a chair. A lot of the impetus for my trip was to shake up routine, be an adventurer, see the world and stay fully childlike-awake to my life. What I didn’t anticipate was that anything can become a routine. Even beauty can become monotonous. No matter what you do, you’re always going to circle back around to complacency or routine. That was a big thing I had to learn the hard way, when I was on the trip and feeling really over it and beating myself up because I’m living my dream, and I don’t want to be here right now. So, what’s going on?

RIF: And you’re learning as you’re on the road. It seems like you could take some time to reflect, but you had miles to make. You had to keep that pace going.

JJ: I didn’t have the luxury of quitting because I was doing everything so publicly. If I just quit this thing, then everyone will know that I’m a quitter, which is one of those childhood lessons that’s hard to shake.

RIF: Do you think the trip changed you?

JJ: I know it did. I didn’t know to the degree it did until I was writing the book—I think by speaking and writing. When it’s just all jumbled in my head, I don’t know what I think. That’s what writing this memoir did: it caused me to look back at things and see how they aggregated into lessons. I wanted it to be my honest processing, free from judgment. And that’s obviously impossible, but I tried to diminish the insertion of lessons and let it be what it was.

RIF: What was it like for you to delve into your experience growing up gay in a Christian household, in a place where your parents were fairly devout? Was that process and reflection cathartic?

JJ: Yeah, it definitely was cathartic. I’m an extrovert, so to go back and remember all these moments that were anchoring or traumatizing or touchstones, and to lay them all out in a story and look at how I came to be the human I am, was something I wish everyone could do.

I believe that openly talking about things leads to healing, and to proper relationships not built on fantasy. It was scary to write about my mom and my dad in honest ways, where I’m like, “Are they going to be offended by this, or are they going to be hurt even though I was very intentional?” I love my parents. They only love me and seek my protection and my thriving. Maybe their perception of how to thrive is different than mine, and so that causes conflict, but their intention is for me to live a happy, prosperous, and wonderful life.

I really wanted to process in the book how there can be conflict without a villain, there can be trauma without a villain, because humans have different perspectives. When my mom read it, she was hurt that I represented her the way I did, which I thought was only pure and loving. She felt so caricatured—that I was painting her as a religious, blind zealot, which I wasn’t, and that was not my intention. It’s got to be very hard for a parent to realize they are the source of their child’s pain. I wouldn’t say she’s the source; American Christian doctrine is the source. But she was a lot of the conduit through which I was taught that, and she still believes that. I’m still navigating that, and I will forever, because I hope to be a writer to write the truth. I have the best mom in the world. I really believe that. So, I’m still learning how to talk about that in ways that honor her and also speak truth.

RIF: I know you brought along eBooks in the form of an iPad and had audiobooks, too. Can you talk about what you read, and what fed your soul, from a literary standpoint?

JJ: One of the ones I read was a history of Latin America written in the ’50s or ’60s, and it was an audiobook. As our cultures have evolved, and we’ve become more careful with language and more respectful of cultures, some of the book was offensive, the way they talked about indigenous people. It was interesting how dated it was, but I love history, learning about Cortez and Atahualpa, and all the historical figures of the conquest of South America, and even pre-conquests, was fascinating while I’m cycling through.

RIF: And traveling some of the same roads that many of them probably did at points.

JJ: Totally. I read Bird by Bird again by Anne Lamott because I knew I wanted to read about writing. I listened to Stephen King’s On Writing, and I read Eat, Pray, Love by Elizabeth Gilbert because I wanted to read another reflective travel memoir, and it’s so famous. I listened to it on tape, and Elizabeth Gilbert is an incredible reader. You feel like she’s sitting next to you, telling you the best story. There’s no affect; she’s a writer who writes like she speaks. I’d download Time magazine every week and read it cover to cover on my iPad, and I felt connected. Ferguson happened while I was down there, and the Ebola breakout in West Africa. There’s certainly something to be said about disconnecting from the world and just being with yourself, which I had, whether I wanted it or not. But it was comforting somehow to keep my toe in the world.

RIF: Are there any other recent memoirs you’re especially excited about?

JJ: I’ve been eyeing Educated. It sounds a lot like The Glass Castle. People are loving it, and I’m a big language person. This is why I like David Sedaris and James Baldwin and Henry Miller. They can write about nothing and I love reading it. They could sit there and write about a bush, and I’m enraptured in the way they see the world.

RIF: The illustrations you have as chapter openers lay out the distances you’ve traveled in lush, whimsical, and imaginative ways. I’d be curious to hear your inspiration for including them.

JJ: I’ve always loved the old journals kept by Charles Darwin and the explorers of the past, where they had no cameras and they were seeing things their culture had never seen before. I love the maps of the 1400s, where they followed the stars and would go around in boats and figure out how to draw massive continents mostly correctly.

RIF: Like Google Maps before Google Maps!

JJ: It’s wild. All that to say, I love that style of hand-drawn black ink; all my tattoos are that style. I do it for a road trip, where I draw a map of where I’ve been with the key memories and the key sites and experiences. And as we were developing this book, my editors asked, “How do you feel about including some of your maps?”

RIF: You’re a super prolific Instagrammer, and it’s a platform you take to organically. It seemed like it helped bolster the journey—once you were featured on their main page, you’re getting into people’s eyes and hearts, and they’re seeing these amazing places you’re going. I’d be curious to hear what you really love most about Instagram.

JJ: I love that question. What I love about it is that I see it as individual magazines you subscribe to, so I publish a magazine. You accumulate the content you’d like to see. It’s very interesting because unlike Facebook and Twitter, which have algorithms that cause you to see things you don’t want to see, Instagram doesn’t allow that, or it minimizes it to a great degree. So, the conversation there is much more civil, much more between friends and that general tone of the environment I like.

Also, I’m a millennial. Most of my followers are millennials, and we love consuming information in small packets. I think the Instagram caption of 2200 characters is exactly the mental capacity of one thought. I don’t know if they hired psychologists, I’m making this up, but that’s exactly how long it takes to make a proposition and defend that proposition: two paragraphs. What’s funny is I’ve been doing it so long now, I think exactly in 2200-character thoughts. I’ll write something organically and go to post it in a caption, and I only have three characters left.

RIF: Wow.

JJ: That’s just the evolution of me doing this for four years. You can be at work, you can be sitting on the toilet, you can be killing time on the couch, and most people on Instagram are not trying to read long captions. But if you’re following me, you know that’s what you’re going to get. Or Humans of New York—you know that’s what you’re going to get. You can get a little nugget, a little thought, a little daily reading that makes your heart swell and maybe challenges something you believe. I get to think in public, to an audience that’s not hostile, to an audience that’s interested in growing and learning even when it’s hard, and that’s an incredible privilege.

RIF: Once you were featured on their page, did you feel that notoriety added pressure to your trip?

JJ: It did, because all of a sudden, I knew most of the people following me are ones I don’t know. There was a time when I wondered, “Is appeasing an audience becoming more important than being myself, and am I going to say something offensive? Am I going to be worried about followers instead of worried about my own personal journey?” That was a fear I had at the beginning, and I learned that my natural disposition is that I can’t be a phony. I’m not a good liar, I can’t wear a mask. So, if you’re not here to hang out with the real me, then you can leave. And then it shed away, and I started being myself and processing things openly, and I saw people were down to have those conversations.

RIF: Do you have any advice you’d pass along to someone who wanted to embark on such an ambitious journey like you did?

JJ: I would say don’t overthink it. Start in your own country, or in a country you’re familiar with. Set a date you’re going to start. Don’t try to prepare for everything. Just get going, get a bike. But if you bike for a few weeks and you’re like, “Shoot, I don’t have a good sleeping bag, I got the wrong tent, I don’t have enough food,” then you can correct. Make sure you start in a place where you can actually correct your patterns before you get into the middle of the wilderness. Don’t just fly to Nepal. It was actually very helpful to start in Oregon, and as I biked down the coast, there were REIs, there were Targets, where I could figure out what I really needed and what I didn’t, and correct my mistakes.

RIF: Have you kept in touch with any of the people you met along the way?

JJ: The people I stayed with in Mexico City and Argentina and Colombia, I talk to pretty regularly, mostly through Instagram. But it’s also interesting: the people I met who don’t have cell phones, who live in really remote places, I’ll never see them again.

RIF: That transience can be beautiful. Given that you’re the executive editor of Wilderness magazine, I’d love to hear if you feel invigorated by the evolving mix of old-school print and modern digital. 

JJ: I’m excited for the fever-fear of technology as a disruptor to settle in, so we just have both. Everyone thought eReaders and Kindle were going to destroy the bookstore, destroy the book, and now they see those numbers are dwindling because people want a physical book. I like a book that you read. It’s not only a psychological journey, but it’s also a trophy of having gone on that journey. I loved reading books on my iPad because I couldn’t carry 50 books. It’s not the same experience lying in a hammock reading an iPad, but it was an experience. I was grateful to have it. I’m just excited that real books are still being read and loved and collected.

RIF: Do you know what your next trip is going to be?

JJ: I don’t. But I kind of love to see what door my life will open for me. As Elizabeth Gilbert says, just follow your curiosity, because that’s where you do your best thinking and your best writing. I’m just going to keep doing that.

RIF: What do you hope readers might take away from reading the book?

JJ: I know for certain that reading a book is an incredibly subjective experience; you never know what’s going on in someone’s life, that it’s going to make them feel understood. I hope the millions of young people who were raised religious and who aren’t completely straight, if any of them read this book, I hope they feel hope and less alone. That they don’t necessarily have to lose relationships with their family, but there is another way. I hope some people with rigid constructs of tradition and religion have those expanded a bit, or can entertain a wider thought and theory. I hope people who feel stuck feel empowered to take a risk and organize their life in such a way where they could shake it up and do something exciting and different. I just hope that me spilling my guts serves people in whatever way they need at that moment.

RIF: And what do you think you learned about yourself from writing this?

JJ: I learned a lot because it was in the writing that I processed the trip, and ultimately my first 32 years. I learned that I’m okay, that I’m loved by God and the universe as I am. I felt that deeply in writing this. I learned that I don’t believe in villains, and that I’m pretty honest. That was something my editors told me, because they were like, “Wow, you’re so brave talking about this.” And I was like, “Really? That’s important to the story.” I realized I don’t really censor myself or censor things just because it makes me look bad. My biggest fear is having a secret that if someone finds out, it would eat me alive. I’d rather just tell you my flaws so no one’s surprised.


Author Photo: Samantha Marquart

JEDIDIAH JENKINS is a travel writer, entrepreneur, and Instagram personality. A graduate of USC and Pepperdine University School of Law, Jenkins began his professional career with the nonprofit Invisible Children, where he helped orchestrate multinational campaigns to end the use of child soldiers in central Africa. His parents, Peter and Barbara Jenkins, are the authors of the bestselling A Walk Across America series. He is the executive editor of Wilderness magazine; his work has appeared in the Paris Review and Good magazine; and his journey was covered by National Geographic.

About Jesse Aylen

Jesse Aylen

JESSE AYLEN is a New York City-based freelance writer, editor, and digital content consultant. When not immersing himself in scads of memoirs and essays, he’s likely tinkering with his website, www.aylenwrites.com.