What Jedidiah Jenkins learned by bicycling across the world

A year-long, 14,000 mile journey through the Americas gave Jedidiah Jenkins new insight on our connectedness

Published September 27, 2018 5:00PM (EDT)

"To Shake the Sleeping Self: A Journey from Oregon to Patagonia, and a Quest for a Life with No Regret" by Jedidiah Jenkins  (Convergent Books/Shutterstock)
"To Shake the Sleeping Self: A Journey from Oregon to Patagonia, and a Quest for a Life with No Regret" by Jedidiah Jenkins (Convergent Books/Shutterstock)

This article was co-produced with Original Thinkers, an ideas festival that uses speakers, art and film to create new paradigms. The 2018 festival takes place in Telluride, Colorado from October 4–7. Original Thinkers logo

Americans are infamous for being workaholics, as foreigners often attest, and as public policy shows: unlike most first-world countries, the United States does not guarantee paid time off, and hence an estimated 28 million American workers do not get paid time off for vacations, holidays or otherwise. The popularity of business and self-help books likewise attests to this: many, if not most, are about making oneself more productive. And yet counterintuitively, Americans also have a long history of dropping out of “normal” society and forging their own path. The American iconoclast’s journey is exemplified in writers and memoirists like Jack Kerouac, Cheryl Strayed, Elizabeth Gilbert, Henry Thoreau and John Muir.

When, at age 30, Jedidiah Jenkins decided to drop everything and ride his bicycle from Oregon to Patagonia on the southern tip of South America, he was joining the latter American tradition of escaping everyday society to contemplate and reevaluate his life. Jenkins described the trip as him “going into a season of intention of reflection, of ‘why do I believe what I believe,’” as he told Salon.

Jenkins’ journey, during which he was often completely alone in remote, lifeless places, was one of personal growth: Jenkins describes processing his sexuality and his religious upbringing, and the complex relationship he has with his parents, who underwent a similar journey in their twenties when his father spent 5 years walking across the United States.

Several years removed from the trip, Jenkins reflects on his experience in a new book, “To Shake the Sleeping Self,” which comes out October 2. A hybrid travel diary and memoir, Jenkins paints a dual portrait of the emotional and physical struggles that it took to brave the 14,000 mile trip — over half the 24,000 mile circumference of the Earth.

Jenkins spoke to Salon via phone about his journey, his book, and his life. This interview has been condensed and edited for print.

There’s a long history of American “extreme” travel writing, where the writer goes off on their own to figure things out. Do you see your writing as in the sort of “great-adventure” travel-writing vein akin to Jack London or Cheryl Strayed or Thoreau?

I would definitely say to be put in that list of people, would be like the honor of my life, that’s an incredible list of human beings. One would hope that like somebody would put me on that list. I mean, our culture doesn’t really have rights of passage where you transition from boyhood to manhood, whatever that means. We don’t really have ceremonies about that. I mean maybe going off to college is as close as we get, but as any observant person would realize, adolescence in modern America is prolonged. You have to self-select when you grow up.

When I was like in my mid late twenties, I was like, “wow, 30 is coming, and when you’re 30 you’re an adult.” I thought, I can’t be farting around, I need to be choosing my life. I’ve really been inspired by Cheryl Strayed, Elizabeth Gilbert, Jack Kerouac, Henry Miller, John Steinbeck — a lot of these writers who step out and seem intentional about the formation of their identity. I felt like so much of my identity had just been the natural chemistry of my mind responding to the work without a lot of choosing. I was like, I want to choose, like I want to feel like I’m in the driver’s seat, to use a term that Cheryl Strayed used.

That’s where I really got this idea, like, okay, when I turn 30 — this was when I was 27 — I’m going to quit my job and spend  a year or more on an adventure and write about it. Because I realized that if I was going to choose my vocation — what’s the thing that I want to bring to the world? — for me it was writing.

I didn’t even know I was a good writer. I’d been told that I’m good, but I needed to cut my teeth and I thought maybe if I do something that’s subjectively interesting, then at least if I’m a mediocre writer , the interesting nature of the thing I’m doing will at least make someone enjoy reading it at the bare minimum. The adventure was not only stepping into a season of intentional reflection, but also intentionally pursuing this project  and writing a book about it.

Interesting. So when you started the trip, you specifically had this book in mind? The idea that you’d write a book after?

Yeah… I thought, I’m going to be stepping into a season of intention of reflection, of “why do I believe what I believe,” “what is the impact of family and tradition and Religion on my life,” “did I choose Jesus or did Jesus happen to me,” those kinds of thing. Also, “what do I think about my sexuality?” in thelarger context of my family and my culture and all these things.

When the trip was over, I didn’t even know what it taught me until I really went back and started writing about it. I didn’t realize I had been changing as it was happening . Because it was more like sand in an hour glass — you can’t see it granularly, you can just see change over long periods of time.

Since writing this book, I’ve become such an advocate of telling people to write down your life, like journal, try writing a memoir, try writing just about your life. Because the clarity that comes from intentionally finding words for yourself, has changed my life truly.

Your trip seems like an interesting reflection on family. On one hand, your parents once did a similar trip around your age, so you had a role model in them. But on the other hand, you were escaping them to some degree, perhaps especially the religious upbringing they gave you.

Yeah, exactly. I felt both indebted and a sense of escape. It was truly like how lucky am I, that what I look at the legacy of my parents, am like oh going on this major adventure and writing about it. I had a model — I can say, “mom, what was it like when you were homesick and miserable sleeping in the woods? I’m doing that tonight, what’s your advice?” Probably most people’s parents would think, “my child has lost their mind.”

That was a really special experience.  But then again, it’s hard because a lot of growing up is finding your identity separate from your parents. They bestowed me with this self-confidence and with this self-assurance to pursue my dreams, which was a gift they gave me, and yes, sometimes that put me in opposition to them. It’s just like, it’s this hard gift that they had to process and I’ve had to process. It’s like you gave me the freedom to spread my wings, but that means I’m going to fly out of the nest. It’s a bitter pill.


It gave me this deep sense of respect and awe and wonder of them, and also it allowed me to see them as young people. When you see your parents not as alien forces but as human beings who used to be in their 20s, and they didn’t know what the future held and all of a sudden they got pregnant and their lives changed, and their still figuring it out, and they’re just as human just like you. They’re not from another planet, they’re not a force of nature, they’re no different than you are.

How did your trip — and, later, the book — change your relationship with them?

Well what it did is that it forced my hand. If anybody is interested in becoming a writer — especially a memoirist — you better get ready to have hard conversations. Because a lot of family relationships are built on the premise that we don’t talk about certain things. When you process all that out loud and in public, it forces hard conversations. There are deep things that I disagree with my parents about, and yes, now they have to see our dirty laundry aired to the public.

I’ve had to really process it, and I’m still figuring out how to do that. I both respect them and respect their privacy, but my actual job is to talk about my private interior life, that’s my career.

It’s a very specific type of career.

Yeah, like if I was a Wall Street Banker, I could go my whole life and never to talk to my mom about my gay boyfriend and just pretend like it’s not happening.

Speaking of relationships, I wanted to ask you about your relationship with social media. You have an active Instagram presence, but also, presumably you had long stretches without technology on your trip. A lot of people, self included, have gone on a trip specifically to get away from the internet.

Yeah, I mean the interesting thing about my trip is that, is that it wasn’t so much that I’m choosing to escape social media. It was put upon me. Like, I’m a week alone on a dirt road, I don’t have the option. It was circumstantially necessary.

That gave me stretches of solitude that were rich in reflection. But then again, I was writing about it publicly to tens of thousands of people who are interested in what I’m doing. I’m living something and I’m also separated from myself watching me do it, and wondering how someone else will perceive what’s happening to me.

It was a multi-layer experience, which is often the experience of a journalist anywhere — like, I’m seeing this as me but I also I’m behind the camera, I’m behind the lens, I’m behind the laptop experiencing it as the story teller. That’s an interesting posture to be in, in general because a horrible thing can happen to you, and one if you’re just present in the moment you’re miserable, because you’re uncomfortable, you don’t feel safe.

On the other hand as a storyteller, watching it happen to you, you’re like, “damn this is a good story.” It actually gives you stamina to survive really hard things, because you see it as the larger context of a story, and that can baptize a horrible moment. I’ve really felt that as a writer, it’s helped me get through a lot of hard stuff.

As you were saying before, American culture doesn’t really have a coming of age model. Yet a lot of Americans are clearly quite inspired by the trip like the one you took. Some probably wish to replicate it. Would you say that it’s the kind of thing that everyone can do or should do?

I mean, the multitude of ways of being human are inexhaustible, so I don’t know about everybody. I’m an advocate of … if you feel the itch to do it, then you should do it. If you don’t and life is good and copasetic and you’re down with the way things are going, then I’m not telling you what to do — keep going. But if you feel a discontent in your spirit, this is a great way to exorcise that demon and to look at your life with a distance.

Of the countries you went through, I’m curious what was the most difficult to communicate or get through?

I was on a bicycle, so the most difficult were the most remote, least hospitable places. For example Baja is a God forsaken desert. There are long stretches where the sun is 110 degrees and there isn’t anybody out there, your only friend is a tarantula. That stretch was the definitely the hardest for me, because it is also right after California where I live. It wasn’t some cute little village where they’re making empanadas and excited to meet an American. There was nobody.

That was early on, so I didn’t speak a lick of Spanish and it was really, really hard. Then this was October — I started in August and so it was September, October and I’m thinking, “wow, a year from now I’ll still be on this God damn bicycle trip.”

I was doing all kinds of mental gymnastics in my head trying to figure out how to get out of this trip. Like I was like, “maybe if I crash my bike and injure myself, then I can get out of it and people won’t think I’m a coward.” But like I said, I had parents with experience doing something similar, so I talked to them. Dad said, “your brain still thinks that it lives at home in a house, it doesn’t realize that home is the road yet. You will acclimate and you won’t feel claustrophobic anymore.”

Would you ever do something like this again?

I feel like I got it out of my system in the sense that I really needed it and it gave me what I needed. But I love the idea of marking my decades. Maybe when I’m 40 I’ll do a motorcycle trip across Siberia and write about it again.

It’s kind of funny, my dad is the first-born son and he walked across America. I’m his first-born son, and I bicycled to Patagonia, like maybe my kid will want to do something similar. I don’t know, that could be a cool family tradition.

Anyway, I don’t have the same desire to escape anymore. I did it, I did escape and I realized the value of community and place… the value of having traditions with your friends that repeat every year. Whereas if you’re always running away, that’s very difficult to have. By stepping away, I learned what it was I loved about staying still.

You’re speaking in a couple weeks at this panel at the Original Thinkers festival in Telluride, in a show called “This is Where We Come Together.” I thought it was interesting that the show you’re in is kind of political — like, the title speaks to the polarized political epoch we’re in. I’m curious if you see your trip as a political act at all.  

I really did. I spent my 20s working at a charity called Invisible Children. We were big believers in global community, and the idea that like, just because I’m a white guy in San Diego doesn’t mean that a child soldier in Uganda is not someone whose life I should fight for. They are citizens of the world too, and if children were being abducted in suburban San Diego we would be in the street marching freaking out, and yet because this is happening on the other side of the world, people don’t seem to care.

I really wanted to test that theory and get out in the world and be exposed on a bicycle, and see if humans are humans wherever you go. I did find that to be true, everywhere I went… it’s a cliché, but our commonality is way stronger than our dissimilarities.

Still, I don’t deny that cultures aren’t very different. I can’t presume to know what somebody’s struggle is in Bolivia, say. There are real differences and yet we have so much more in common than we don’t. I don’t know, my “global citizens” beliefs got complicated on the trip. I think, if you want to fight for someone else, you have to learn a lot about them.

Coming back to a divided America was a really profound experience, because I had just spent so much time with people that were so different than me, and to see America rolling into like-minded echo chambers was… like, it seems like now if you have different political beliefs than your family members, you feel like they’re truly alien to you. That’s a big problem if you’re trying to find common ground and you’re trying to actually have a sense of national or global identity.

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Jedidiah Jenkins’ book, “To Shake the Sleeping Self: A Journey from Oregon to Patagonia, and a Quest for a Life With No Regret” comes out on October 2, 2018. Jenkins, along with Roland McCook, Marika Anthony-Shaw and Wally Green, will be speaking at Show 1, “This is Where We Come Together” at the Original Thinkers festival in Telluride on October 5, 2018.

By Keith A. Spencer

Keith A. Spencer is a senior editor at Salon who edits Salon's science/health vertical. His book, "A People's History of Silicon Valley: How the Tech Industry Exploits Workers, Erodes Privacy and Undermines Democracy," was released in 2018. Follow him on Twitter at @keithspencer, or on Facebook here.

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