Interview: On Shaking the Sleeping Self

with Jedidiah Jenkins

On Shaking the Sleeping Self

Many people dream about leaving their jobs to travel the world, but Jedidiah Jenkins is one of the few to turn that dream into a reality. Finding himself dissatisfied with his day-to-day life and eager to make a stronger connection with the natural world, Jed upended everything and embarked on a sixteen-month, 10,000-mile bicycle trip that took him from Oregon to Patagonia.

This experience is the subject of Jed's bestselling memoir To Shake the Sleeping Self. In early February 2021, he published his second book, an essay collection called Like Streams to the Ocean. It’s full of profound reflections on topics like ego and love and the things that make us who we are. 

Jed is brilliant and hilarious, and what an honor it was to host him for a Studio Visit. This interview is excerpted from our conversation and edited for clarity.

You can watch a replay of the Studio Visit with Jedidiah Jenkins here.

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Suleika Jaouad: Jed, I’m really interested in your path to becoming a writer. I know your parents are writers. Their five-year walk across America was featured on the cover of National Geographic, and they documented that adventure in their bestselling books, A Walk Across America and The Walk West. I imagine you were raised in a household where creativity was encouraged. But you chose a very different path, at least at first. Tell us about that.

Jedidiah Jenkins: I don't know how you feel about this, but my career path is so interwoven with how my personality developed as a child, and the influences of my childhood and the interplay of all those factors. So yes, I grew up with writer parents. I was very encouraged and believed that any job was a real job. 

I grew up wanting to be a movie director. My hero was Steven Spielberg, and I wanted to move to Hollywood and be him. My parents fully supported me. They weren't, like, “That’s a pipe dream”—because they both grew up in public housing, very poor, and were told they couldn't do it. And they walked across America and became bestselling authors. So they modeled for themselves and then for me that nobody can tell you what you can't do.

But my parents divorced when I was very young, and I grew up with a single mom. My older sister was very rebellious and had substance abuse issues, and my little brother had really serious medical issues. And my mom was pulling her hair out, trying to keep my sister out of jail and my brother alive. I knew I couldn’t rock the boat. I couldn’t have needs, I couldn’t shake up this house, or it’ll come crashing down. So from a very young age, I became totally autonomous. I need to be invisible and do my own thing.

What’s so funny is I went off to film school, and then I realized, Oh, no, a movie director is actually not just an artist, but the boss of 300 people—and I am not meant to be a boss. No, no, no, no. I don’t even know how to tie my shoes. I can’t spend some company’s $40 million, and boss people around and fire them. That was when I realized, “I’ve made a huge mistake,” and I panicked. I thought, I need a real, bankable skill. So I went to law school and became an attorney. Straightaway from that I went to work for my friend who had started a charity called Invisible Children. I was their in-house counsel, and then my role there evolved. This is in my mid-to-late 20s.

SJ: Around that time, you started thinking of going on a journey—which was not just some touristy boondoggle, but a deeper quest. Recently I was rereading To Shake This Sleeping Self, and it occurred to me that you were having a kind of quarter life crisis. You write, “The carefree timelessness of my youth was rattled in my 20s, a kind of panic set in.”

JJ: So it wasn’t that I’d had enough and panicked and cut the cord and jumped ship. I thought, I’m going to be 30 in a few years—and that’s an adult. So I should probably figure out if I’m living the life I want to live and if I’m becoming the person I want to be. But I knew I’d find some reason to change my mind, so I decided to tell everyone I was going on this journey.

The power of speaking something into the universe is that it’s listening. When I spoke that, it began to live in my community, so they held me accountable. They would ask me, “Are you riding your bike? Where are you going to sleep?” The more people asked me, the more I thought that if I didn’t go, then I would be seen as a coward. I basically weaponized my pride to force myself to do something, and it totally worked.

SJ: I’m all for forcing myself into accountability. When I first had the idea for the Isolation Journals, I started emailing people I admired, asking them to contribute prompts. Then when they started sending prompts, I thought to myself, “Oh, shit, now I actually have to do this.”

It’s interesting to interrogate what compels us to speak such things into existence to begin with.

JJ: The things that I find to be my passion or my purpose are directly linked to my woundings, specifically in my childhood and adolescence. The things that give my life the most meaning are the richest injustices that happened to me—specifically being a gay little boy raised in the Evangelical South. Being gay in an oppressive society is a unique minority problem.

What I mean by that is, unlike most ostracized groups, being gay happens to you alone for a while. On the playground, you might realize you’re different because of your skin color or your culture, and you go and you say, “Mommy, I'm different.” And she says, “We have each other though, we’re gonna do this together.” Whereas when you wake up and realize something is different, and you are in a culture and a family that does not affirm that, you experience incredible internal isolation. You fear who you are is sinful and going to kill you, and maybe kill your immortal soul. 

So in high school and college, I was obsessed with being the best and the goodest boy. Picture a golden retriever wagging his tail. I was student body president. Bible study leader. Campus Crusade for Christ. Trojan of the Year at USC. Because deep down inside me, from the earliest moments of self-reflexive consciousness, I knew that some integral part of my identity was rotten and evil.

I also became super outdoorsy. Now, I’m not saying I’m not outdoorsy. I am. But it is interesting to think that was partly something I viewed as hetero-normatively masculine—to be in a flannel with an axe in the woods. It’s like I was trying to be some character, so that I could overcome my internal fear of my own feminine energy. What’s more hyper masculine than traveling on a bicycle for 14,000 miles and sleeping under bridges and climbing mountains?

Granted, this is the confusing quilt of human identity—that it could be a response to fear of being ostracized as a child, and that could also just be my personality. But you think about a kid whose very existence feels scary, going on a great adventure to discover the world and becoming a writer to put into words, not only what he thinks, but also explain and adjudicate his case to the world of why I’m worthy and I deserve to exist and I’m not bad. That became my career, excavating what’s burning underneath. And for me it was the fear of rejection.

SJ: I was around the same age as you when I embarked on my own kind of epic journey—in my case, a road trip. I was the most lost I've ever been, and I was reading about rites of passage. These ceremonies that allow us to shoulder complicated feelings, that keep us from getting lost in transition, that help us bridge the distance between no longer and not yet.

I’m curious if your trip felt like a rite of passage? I know you said you were afraid of rejection, but was the thing on the other side a kind of acceptance—and if so from whom?

JJ: It really was! In my new book, Like Streams to The Ocean, I write a lot about this therapy retreat center called On Site, which is in rural Tennessee. It’s gorgeous. And one of the things they do is create the space, so you can act it out, which can feel very silly when you're a grown-ass man. They say, “You’re a nine-year-old little boy. Where’s your mom?” Okay, my mom’s right in the middle. “Where’s your sister?” Under my mom’s arm. “Where’s your little brother?” At her feet. “Where’s your dad? Why are you over in the corner playing by yourself?”

What the therapist explains is that the human brain doesn’t just think in words. It thinks spatially. When you close your eyes and picture moving through your childhood home, you’re remembering it in 3D.

All of that ties into this concept of a rite of passage, where you embody and you act out a metaphor for life change, for transition, for transformation. You give it a little trip or a big trip, or you give it a tattoo, or you burn something in the fire and let it go at the beach. You’re putting spiritual cosmic truth into a metaphor, so that your brain is like, “Oh, I get this.”

That therapy changed my life. I’m a talker and a writer, so when a therapist asks me a question, I can talk my way around it all damn day. It would never make me cry because I’m so cerebral and I’ve built a really serious fortress of ideas. But if you get me acting it out and making my little self go over there and, because I wished my mom would have hugged me, I make these two strangers hug each other—and I’m sobbing because it’s unlocked some spatial access to an emotional truth that I had built a fortress around my words to get to.

So to answer your question: The bike trip really was a rite of passage. The trip was the metaphor and writing the book unpacked what the trip meant over the two years it took me to write it. What it really meant was that being good and being performatively perfect is not what’s going to save me. What's going to save me is being authentic and standing strong and being who I am.