The Great Discontent

The Great Discontent

Jedidiah Jenkins

Jedidiah Jenkins

  • writer

At the age of 30, Jedidiah Jenkins quit his day job and embarked on a 16-month, 10,000-mile bike trip from Oregon to Patagonia, Chile, the self-imposed catalyst for pursuing his dream of writing a book. After garnering a massive online following for writing about his travels, he has since returned home to LA, where he recently launched a magazine, Wilderness, and is currently working on a book about his cross-continental adventure.

Tell me about your path to what you’re doing now. I grew up in Nashville, Tennessee, to parents who were both creative. Back in the ‘70s, they traveled across America for five years and wrote about their experiences for National Geographic. Their journey captured the imagination of America because the country was having an identity crisis at the time—the Vietnam War was going on, the president had left office, and everything was a shitshow. I don’t want to call them eccentric, but it didn’t surprise me when they got divorced in the ‘80s. Being raised by two free spirits meant that the conventional track most humans find themselves on—the assembly line of life—didn’t tempt me like it does others. My parents told me, “Go, do, be, and dream. There’s nothing out of reach, and you can have an unconventional life as long as you’re true to yourself.”

I studied creative writing and film at the University of Southern California. Unfortunately, after pursuing the creative arts, I felt like the right side of my brain had been so overly represented that I had no raw, marketable skills. At age 22, it’s intimidating to suddenly find yourself thinking, “I am never going to find a job and I can’t pay rent—what am I supposed to do?” Like many people, I contemplated law school and thought I might enjoy it, so I decided to go. I became very convicted knowing that I could decide to go, when many didn’t have that choice. I felt like I owed it to my privilege to try. Law school was formative in teaching me about how legal theory shapes civilization, and it really affected me. Eventually, while working at internships after graduation, I realized that I didn’t actually want to work at a big law firm. I had been raised by creative parents and so creatively developed up to that point that it felt constricting to work in a giant machine that existed solely to make money.

Around that time, in my mid–twenties, I went to go work for some friends of mine who had started a nonprofit called Invisible Children, which focuses on activism to end the use of child soldiers in Central East Africa. Invisible Children was where I discovered that I love putting complex ideas into words and that I actually wanted to become a writer. At the time, I was working as a lawyer, but I kept being pulled into storyboard meetings to help write for documentaries and campaigns. My coworkers liked how I phrased things, so I’d write up voiceovers for them. Over time, I was phased out of my lawyer position and worked solely as a writer for Invisible Children for a number of years.

It’s funny how the universe conspires to change your mind or set you on a certain course. When I was 27, I read Malcolm Gladwell’s book, Outliers. In it, he talked about the “10,000-Hour Rule,” which made sense to me, even if it’s not hard science: if people dedicate 10,000 hours to something, then they become an expert in it. That concept made me think about what I wanted to become an expert in. Youth movements? Millennial activism? Making documentaries? I considered a lot of things, but I kept coming back to my desire to write a book. Then I wondered, “How am I going to write a book? I’m too young to have anything worthwhile to say.” I remembered the quote from Benjamin Franklin: “Either write something worth reading or do something worth writing.” I thought to myself, “Well, what if I can do both?” What if I could do something objectively interesting and then write about it?

I decided that when I turned 30 I would take a year off to go on a bike trip from Oregon to Patagonia and then write a book about it. I realized that if didn’t do it, I would go deeper into the nonprofit world, wake up as a 65-year-old expert in international criminal law, and think, “Wow, I never chased that dream I wanted to chase.” Even if my book ended up being no good, at least I had tried. I could always go back to what I already knew how to do, but I wanted to do something while in my relative youth to get that nagging feeling—that great discontent—out of me.

I believe deeply in the power of speaking your dreams into existence. So many people have dreams they want to pursue, but they’re afraid to talk about them because they don’t want to fail or have others hold them to it. They ask, “Who am I to do that?” So I scared myself into going after my dream by telling everybody. I gave my three-year notice at my job, and they were like, “That’s not a thing.” (laughing) Once I did that, it led to me speaking it into existence: I talked openly about it on my blog and social media, and people started saying, “We can’t wait for your book. It’s going to be so cool!” Because of that, literary agents started approaching me about making the book happen. My community began to hold me to it, which forced me to do it even when I felt scared. As the start date approached, I thought, “Well, I can’t not do it now.”

Everything started to happen before it happened because I talked about wanting it to happen. I’m not trying to sound brave, but I was willing to scare myself by setting high expectations for what I wanted to do.

“I decided that when I turned 30 I would take a year off to go on a bike trip from Oregon to Patagonia and then write a book about it…I wanted to do something while in my relative youth to get that nagging feeling—that great discontent—out of me.”

Florence, Oregon
Florence, Oregon

How long ago was the trip? I started in August 2013 and finished in late December 2014. I’ve since spent this year working on the book and launching a magazine called Wilderness with a couple buddies. It has been so fun.

And you did a Kickstarter campaign, too? Yes, I did a Kickstarter campaign for the book, which is how I’ve survived this year. I did that because, A, I ran out of money on the trip and, B, I was afraid that because I had run out of money, I would have to make a book proposal before I had written anything or had time to let all of my thoughts and experiences from the trip settle and distill into something meaningful. I knew that if that was the case, I’d have to guess at what the book was going to be about and sell it to a publisher, who would then own me and say, “We want you to write the next Eat, Pray, Love or the next Wild!” I like those books, but I don’t think my book is going to be exactly like that. I was terrified of being muscled into writing a book I didn’t want to write because I was broke, so I asked the community that trusts my voice to help me get there. They did, and it has been the most incredible commission to excellence to have such a community of people expecting greatness.

Going back to your childhood, was creativity cultivated in your family? Yes, big-time, and I had the distinct luxury of parents who didn’t live vicariously through me. They’d say, “Oh, you like drawing comic books and being a nerd and playing in the woods? That sounds great. Go do that.” Me not being good at a lot of the traditional Johnny-High-School things led me to explore identity in other ways.

Your family has a legacy of adventure. Did you ever imagine yourself going on an adventure like your parents did? I didn’t think I’d follow in my parents’ footsteps at all. Going on this trip and becoming a writer felt totally original to me. For a long time, I didn’t see my parents as real human beings who were young once and made risky decisions and went on adventures—it didn’t cross my mind that it could have come to them as spontaneously as it came to me. I’m glad my parents never projected their dreams onto me, because there’s something to letting people flourish to become what they are: a lot of times, they become the very thing you hoped they would become.

Florence, Oregon
Florence, Oregon

“I’m glad my parents never projected their dreams onto me, because there’s something to letting people flourish to become what they are: a lot of times, they become the very thing you hoped they would become.”

Have you had any mentors along the way? Definitely, although mentorship is such a lost idea in modern culture. Growing up, most people don’t typically spend a significant amount of time with older people apart from family members. For instance, if you’re in high school, everyone you know is in high school; when you go to college, almost everyone you hang out with is college-aged. So many people go through crises because they don’t know what to do during different seasons and stages of life, but it would be so much more manageable if you had someone 10 or 15 years older than you to say, “It’s going to be okay. Here’s how you do it.” I didn’t have those people to talk to until I was in college and started to make friends who were older than me. Through those friendships, I found confidence to no longer fear the stages of life that came, but to choose to press into them and become the person I want to be.

One of my mentors is Tom Shadyac, who’s in his mid–50s. When he speaks, I think, “Wow, you have thought all of my thoughts, only better, and you’ve tried them out.” The relationship I have with him has really helped shape my mind. I’m so grateful for it, because now I’m excited to be in my 50s and pour wisdom into people the way he has poured his wisdom into me and so many others.

Was your trip from Oregon to Patagonia a mentor or teacher to you, and what was your biggest takeaway from it? There were so many takeaways, but one that stands out is that when you chase an intention, people support you. When they see something manifested in you, even if it’s not exactly what they want to do, they think, “Finally, someone’s going after something.” That’s exciting for people.

I thought I’d feel more alone on my trip. I thought I would get more pushback with people asking, “Why are you being so irresponsible?” Instead, I heard, “You can do it. We’re right here with you,” and, “Oh my gosh, you haven’t posted anything in three days. We hope you’re safe.” I’ll never forget the woman in North Carolina who left a comment on one of my Instagram posts that said: “I’m a mother of four, and I can almost never leave the house. Watching you chase this dream feels like I’m chasing it, too. I feel like I’m seeing the world, and I am so grateful for that.” I never anticipated those types of responses, and it really helped me during the times I was miserable, uncomfortable, annoyed, and homesick.

The trip was for me. I never meant for it to be anything more than an exploration into self and pushing my own limits. But when I realized that people were getting something out of it, I took on a responsibility to them. Whenever the trip became difficult, I treated it as if I was a reporter; all of a sudden, I felt a sense of duty, which helped get me through really uncomfortable situations. If you’re only doing something for yourself, it’s easy say, “Fuck this. I’m tired.” But if you’re doing it for other people, then you tell yourself, “I can make it another day. I can keep going.”

“The trip was for me. I never meant for it to be anything more than an exploration into self and pushing my own limits. But when I realized that people were getting something out of it, I took on a responsibility to them.”

Mexico City, Mexico
Mexico City, Mexico
Teotihuacan, Mexico
Teotihuacan, Mexico

So you do feel a responsibility to contribute to something bigger. Yes, but I’m wary to directly name it. People can only testify to their own experiences and the vulnerability that comes from being raw, expressing weakness and delight, shucking skepticism, and having hope in the world and other people. Those are things I believe in and want to be about. I feel a responsibility to be true to myself, and in so doing, that liberates others to be true to themselves. In that way, I feel motivated by a responsibility to contribute. But beyond that—like having a political or spiritual mission—I’m in a season of learning, so I teach or speak only what I am processing, not that which I have arrived at. That in itself is a duty.

Now that your trip is over and you’re spending time writing, are you creatively satisfied? I am so creatively satisfied that I can’t even deal with it. It is so wonderful. Sometimes I have out-of-body experiences where I cannot believe that I get to sit at a coffee shop and write about the world and my life and think that somebody, somewhere, gives two shits about it. I cannot express enough how lucky I feel.

Considering where you are now, what are your ambitions for the coming years? I love public speaking, telling stories, and connecting with people, so I would like to do more of that in the future.

As far as adventures go, I’m not sure what that will look like. When you’re climbing a mountain, you have no idea what’s on the other side. Climbing the mountain of this book means that I don’t know how it’s going to be received or if I’m going to go on book tours. I don’t know what doors are going to open, but I do know my nature, and every seven years or so I start itching to do something weird and fun. I would love to sail a boat from Los Angeles through the Panama Canal and around to Rhode Island, where my aunt lives. Or maybe I’ll ride a motorcycle across Europe or Mongolia. Who knows? I will definitely go on more big adventures in my life, but I don’t yet know what those will be.

“I believe that travel is a teacher, one that wakes up your senses when you’re out of your comfort zone…It allows you to see the world with fresher eyes and realize that life doesn’t have to be a certain way. We could and can be better.”

Bogota, Columbia
Bogota, Colombia

What advice do you have for someone starting out? I’ve been thinking about the why behind the why. In my case, I thought I wanted to be a film director because I like telling stories—that was my first why. But when I moved to California and studied directing, I realized that I hated it. I learned that directors are basically the boss of 200 people, and I am not good at that. I felt lost. I knew I wanted to tell stories, and when I asked myself why, I realized it was because I liked to connect with people. I recognized that I enjoyed the storytelling part of being a director, but not the boss part, and that’s when I decided to switch to creative writing. All of a sudden, I had found the fulfillment in writing that I thought I would find in directing. My advice to people starting out is to follow your curiosities, hold your goals loosely, and try to figure out what you really want.

If you can dive into the heart of what motivates you, then you start to recognize the many forms your dream can take that you wouldn’t have considered before. Right. There’s a difference between a dream and a goal. A dream is something in your spirit that you need to produce, say, or do. A goal is what you think the manifestation of that dream is. People feel like they fail when they don’t reach their goals, but sometimes your goals are only a rung on the ladder of figuring out your dreams.

Exactly, and social media can make those failures feel worse. There are many amazing things about how connected our world is, but it’s easy to see a post and say, “Well, so-and-so did this, so if I want to be successful, then I need to do it, too.” You fall into the trap of comparing yourself to others. People beat themselves up when they don’t get what they thought they wanted. Instead, they need to look deeper into their hearts to recognize that what they actually want has many faces.

“I believe in the goodness of humanity, and I find human beings so beautiful. I think it’s our self-hatred that creates feverish little monsters that go around hurting people. If we understood that we are all lovely and lovable, we would hurt fewer people.”

Perito Moreno Glacier, Argentina
Perito Moreno Glacier, Argentina
Torres del Paine National Park, Chile
Torres del Paine National Park, Chile

I really love that. You grew up in Nashville, but are now based in LA. How does living there influence you? Nashville is such a cool city, and I love going back there. But the moment I came to LA, I felt like a zebra that had been raised in a zoo all its life and was loosed on the Serengeti. It was, “Oh, this is where I’m supposed to be!” I immediately felt at home.

I am in love with LA for so many reasons, one of which is that I’m surrounded by dream-chasers. In this city, if you want to make a children’s book or start a french toast food truck, no one says, “Pfft, get a real job!” Everyone here says, “Do it!” I can imagine how creative people in other cities chasing a dream might feel lonely because their community doesn’t identify with or support what they’re trying to do, so I’m grateful to be part of a community where everyone is trying to make something happen. That’s inspiring to me, and I feel like I’m in the midst of a churning machine of ideas.

How does traveling influence you differently than when you’re home in LA? I believe that travel is a teacher, one that wakes up your senses when you’re out of your comfort zone. It makes you realize how different things could be. It allows you to see the world with fresher eyes and realize that life doesn’t have to be a certain way. We could and can be better.

Although you’ve traveled far, in some ways your journey is just beginning. As you continue to put work out into the world, have you thought about what kind of legacy you want to leave? I want to put words to people’s thoughts. I want people to say that I not only helped them feel less alone, but also stronger, more contemplative, and more free.

I believe in the goodness of humanity, and I find human beings so beautiful. I think it’s our self-hatred that creates feverish little monsters that go around hurting people. If we understood that we are all lovely and lovable, we would hurt fewer people. I want people to think of me as someone who made them feel that way.interview close

The Thousand Year Journey: Oregon To Patagonia; a film by Kenny Laubbacher

“A dream is something in your spirit that you need to produce, say, or do. A goal is what you think the manifestation of that dream is. People feel like they fail when they don’t reach their goals, but sometimes your goals are only a rung on the ladder of figuring out your dreams.”