To Shake the Sleeping Self: A Journey from Oregon to Patagonia, and a Quest for a Life with No Regret

To Shake the Sleeping Self: A Journey from Oregon to Patagonia, and a Quest for a Life with No Regret

by Jedidiah Jenkins
To Shake the Sleeping Self: A Journey from Oregon to Patagonia, and a Quest for a Life with No Regret

To Shake the Sleeping Self: A Journey from Oregon to Patagonia, and a Quest for a Life with No Regret

by Jedidiah Jenkins


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NEW YORK TIMES BESTSELLER • “With winning candor, Jedidiah Jenkins takes us with him as he bicycles across two continents and delves deeply into his own beautiful heart.”Cheryl Strayed, author of Wild and Tiny Beautiful Things
On the eve of turning thirty, terrified of being funneled into a life he didn’t choose, Jedidiah Jenkins quit his dream job and spent sixteen months cycling from Oregon to Patagonia. He chronicled the trip on Instagram, where his photos and reflections drew hundreds of thousands of followers, all gathered around the question: What makes a life worth living? 

In this unflinchingly honest memoir, Jed narrates his adventure—the people and places he encountered on his way to the bottom of the world—as well as the internal journey that started it all. As he traverses cities, mountains, and inner boundaries, Jenkins grapples with the question 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.

A soul-stirring read for the wanderer in each of us, To Shake the Sleeping Self is an unforgettable reflection on adventure, identity, and a life lived without regret.
This edition features a new afterword and a reader’s group guide.

“[Jenkins is] a guy deeply connected to his personal truth and just so refreshingly present.”Rich Roll, author of Finding Ultra
“This is much more than a book about a bike ride. This is a deep soul deepening us. Jedidiah Jenkins is a mystic disguised as a millennial.”—Tom Shadyac, author of Life’s Operating Manual

“Thought-provoking and inspirational . . . This uplifting memoir and travelogue will remind readers of the power of movement for the body and the soul.”—Publishers Weekly

Product Details

ISBN-13: 9781524761400
Publisher: The Crown Publishing Group
Publication date: 12/31/2019
Pages: 352
Sales rank: 62,488
Product dimensions: 5.10(w) x 7.90(h) x 1.00(d)

About the Author

Jedidiah Jenkins is a travel writer, entrepreneur, and the New York Times bestselling author of To Shake the Sleeping Self. 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. Jenkins’s work has appeared in The Paris Review and Playboy, and he has been covered by National Geographic.

Read an Excerpt

Chapter 1

The Plan

In early 2011, I told my friends and coworkers. I posted a map of South America on my Instagram. “When I turn thirty, I’m cycling to Patagonia.” Some people cheered me on. “Fuck, yeah!! Go get ’em!” Other people laughed. “Isn’t it a little early to be telling us your plans three years from now?” “No,” I said. “Gotta speak it into existence.” Other people shamed me. “Don’t be so self-­congratulatory. You haven’t even done anything yet. Hit us up when you’ve actually done something.”

I soon told my parents. They are divorced, so it was two separate calls. Always my mom first. They were thrilled initially. “Following in our footsteps, I see,” my mom said.

I hadn’t even considered that fact. My parents walked across America in the ’70s. My dad was in his mid-­twenties, my mom in her late twenties and early thirties. It took five years, and they wrote about it for National Geographic. They were even on the cover—August 1979, if you want to track it down. They were in search of America and themselves in the middle of the cloud Vietnam cast over this country.

They went on their spirit quest. And now I was going on mine. Who was I to think I had come to this idea completely on my own? As my mom began cautioning me to the dangers of cycling across Mexico, my mind was off somewhere else, thinking about destiny and the pre-­ordering of things. How so often we become our parents, whether we like it or not. I had walked right into Mom and Dad’s shadow without noticing.

Let me digress about them for a minute. They became famous from their walk. They wrote best-­selling books about it. They traveled the country speaking and doing interviews. They were next-­to-­household names. They also became famously Christian. My dad’s testimony was raw and dramatic: a New England kid from public housing who went to Woodstock and did drugs and never found a rule he couldn’t break. He found Jesus on the walk, at a charismatic revival meeting in Mobile, Alabama. He found my mom in a seminary outside of New Orleans—an angel-­faced girl from the Ozarks who loved the Lord and knew Scripture better than anyone. Her voice and soft skin gave her the appearance of someone who’d jump at the sight of a mouse. But she was fearless. She’d grab a snake right out of the grass. When my dad met her, he turned on all the charm he could muster and seduced her out of seminary. “Marry me and let’s walk to Oregon.” Can you imagine? She said yes. I exist because of it.

After the walk and publication of the National Geographic story and the subsequent best-­selling book, they traveled and enjoyed their fame and worked on new books together. Somehow, they managed to represent both the counterculture of 1970s youth and the wholesome churchgoing middle. They were curious about America. They loved Jesus, but didn’t fear the differences of human beings. For a moment in the sun, they were America’s dusty sun-­kissed sweethearts. They had three kids (I was the middle baby) and bought a farm in Tennessee.

Then, at the height of it all, their marriage fell apart. The perfect couple crashed. Dad was gone a lot. He kept traveling, writing, speaking, and apparently doing other things. My mom was home with the kids. Maybe my dad’s charisma got the best of him. I remember him talking to a Waffle House waitress with no teeth for an hour. He’s the type of man who sees a dead-­end gravel road and turns down it just to know how far it goes. Maybe his best quality was his Achilles heel. I was a little kid at the time. I don’t know what really happened. She told him to quit cheating, and she later kicked him out. Their empire fell. And nothing falls quite like a Christian celebrity.

But through all the mess of divorce and parenting and maintaining public personas, my parents were excellent to us kids. Weekdays with Mom and weekends with Dad. Mom making art projects at night with us. Dad taking us out on the tractor to feed the cows. Whatever storms were happening between them, in their careers and finances, I had no idea. And in spite of it all, they remained explorers to the core. They had walked America’s backroads and mountains and deserts, and they would raise their kids to love them the same. Even if they had to do it separately.

We didn’t have much money growing up. Writing a couple best-­sellers will keep you afloat for a while, but if you can’t keep it up, the money runs dry. Add in three kids and an expensive divorce, and it gets hard. But my parents knew how to live on a little. Instead of flying to islands or going on ski trips, we went camping. We took long road trips to see the Grand Canyon, the Badlands, the Wild West. My mom would plug in the camper and I’d disappear to the creek, or down a canyon, and come back hours later with a turtle or a bone.

Mom and Dad never pressured us to become adventurers, and they mentioned “The Walk” only in passing. But they taught me to look around, to explore, and that it didn’t cost a whole lot of money to do it. They always told us that we could do whatever we wanted, be whatever we wanted. They had the American dream in the twinkle of their eyes. Both had been rewarded, even if only for a moment, with the fame that comes from taking a chance, risking it all for an idea that awakens the soul.

The point of bringing up their parenting style is this: somehow, my parents had tricked me. They had made me respect them and want to emulate them, all without me realizing it. And comically, I came to the conclusion that I wanted to go on a great adventure in a way that felt completely original to me, and spontaneous. Like I was the first person to ever think of such a thing.

I didn’t do much prep for those next three years. I continued to work at the charity and build campaigns and work on documentaries. But the coloring of those years was different. I knew I’d be leaving as soon as I turned thirty. I knew I had a giant adventure on the horizon. This knowledge changed the way I perceived time. My job felt more important. I took on more responsibility, and worked harder because I only had so much time to get things done. I stopped feeling trapped. I had an escape stomping my way. You might think I would’ve ridden my bicycle and trained, but nope. I didn’t do shit. I guess I was confident that I could ride a bike (I didn’t even own one), and that I’d learn as I went. Or maybe training would’ve made it too real. Too scary.

Thank God I told people about my trip, I thought. If I hadn’t, it would be so easy to not do it. I would’ve changed my mind a hundred times. The inconvenience of uprooting my life, of stepping away from all that I had built, was enormous. But the questions had never ceased. “When do you leave?” “You still doing that crazy trip? I’m so jealous!” “Have you been training?”

Then, quite suddenly, it was 2013, and I was thirty years old, and it was time to leave. Whoa. I had looked down and it was here.

I googled and read cycling blogs. Some had incredibly detailed maps and warnings and packing guides that measured out the weight of this and the weight of that. Some bloggers were so ill prepared, their journals read like Shakespearean tragedies. I thought of my inspiration, Andrew, the one who had done the trip before. I had to talk to him. I e-­mailed him. He was off training new employees in Uganda. I needed a pep talk. I was overwhelmed.

“Don’t plan too much,” he wrote. “You can’t assume that a map tells the truth in Central and South America. Just know that you need to make it forty to sixty miles south on each travel day. Trust the locals. Ask the people you meet what’s the best way to go. The most beautiful. Let the place tell you where it wants you to go. The worst thing you can do is assume you know now what you’ll know then. And don’t let anyone else dictate your trip for you. If you want to take a bus sometimes, take a bus. If you need to hitchhike, hitchhike. It’s your trip, not anyone else’s. If you try to be too fanatical about it, you’ll spend more time stressing out and less time seeing a place for what it is.”

I liked the sound of that. I picked a date, five months out. I’d start on August 28 in Oregon. I would travel south, mostly along the Pacific Coast, cross the Darién Gap in Panama, and follow the Andes from Colombia all the way to Patagonia, the very bottom of the inhabited planet. The whole thing would take sixteen months. The timing was important: I needed to follow the dry season. If you hit Central and South America during the rainy season, you’re soaked for months. If you hit them in the dry season, you will have only sunshine. And if my pace was correct, I would also hit Patagonia in its spring/summer, which would be November and December 2014. I had to time it right, because Amazon rainy seasons and Patagonian winters would ruin me and possibly send me home.

Two months before launch day, I walked into REI and found the bike guy. The people who work at gear stores usually frighten me. So many times I had tried to buy a sleeping bag, or running shoes, or a tent, and the guy made me feel like an idiot. They can get a tired tone in their voice, exhausted from explaining to so many basic bitches how the forest works. If I had started this trip at twenty years old, I would have trembled as I asked him what kind of bike I should use for a sixteen-­month trip through Latin America. But thirty is different. By thirty, I had learned a valuable lesson: You are not an idiot. It’s okay if you don’t know everything. Don’t pretend. Ask all the questions you want. It’s fine if you’re not prepared for the zombie apocalypse at all times.

So I walked in, told the young guy I needed a bicycle that could get me to Chile. He cocked his head like a dog and asked me if I had been training. When I said no, a confident “nope,” he called for some old guy in the back. “Richard’s ridden his bike across the U.S. three times,” the young guy said. Richard’s legs were bowed and his hair was white and thick. His hands were black with grease. He looked me up and down and must have decided it wasn’t worth his time to discourage me. “You should go with the Surly Long Haul Trucker,” he said.

He motioned to a relatively simple-­looking bike hanging on the wall. It looked thick and heavy. It had no fanciness about it. It didn’t look fast or sleek. It was just a dark green bicycle.

“If you’re headed into South America, you don’t want a fancy carbon bike. That thing breaks, you’ll be hitchhiking the rest of your trip. You want steel. Any mechanic can weld steel if you get hit by a car or a bus. This Surly is tough as hell. It’s heavy, but sturdy. That’s the one you want.” He showed me the multi-­tool I should get, which is basically a Swiss army knife for bikes, and he also said I needed panniers.

“What are panniers?” I said.

He looked at me for a silent beat, certainly thinking, This boy is going to die.

“They are saddlebags that you hang from the side of your bike.” he said.

I did exactly as Richard said and bought it all. Instead of a tent, I bought a hammock. I wanted to be off the ground, away from critters. The wise man continued, “If you’re going to sleep in a hammock, you’ll need a reflector pad underneath you to hold in your body heat. Or else you’ll freeze. But don’t buy one here. It’s forty bucks. Go to Wal-­Mart and buy one of those dashboard sun reflectors for five bucks. It’s the exact same thing.” God bless this curmudgeon. Bingo.

The e-­mails from my mom never stopped. And the calls. She called me at the office a few months before my last day.

“Jed,” she said, which in her southern drawl sounds more like “Jayud,” “I just don’t know about you going through Mexico. It’s too dangerous.” I could hear grunting through the phone as she moved her shih tzu off the bed. “Okay, let’s get you some food,” she mumbled, distracting herself with the dog to minimize the electricity of confrontation.

“Mom, I’ve been to Mexico many times. Everyone I speak to who’s been there says it’s misunderstood and beautiful. They say Fox News makes people scared and think that it’s only cartels and freeloaders wanting to get here.”

“Well, how could Mexico be so great if they all are trying to come here?”

“I don’t think that’s true. They’re not all trying to get here.”

“I’m just worried about you. I don’t want you cycling alone. I know you’re going to say that I walked across America and my parents were worried about me, but it’s different. America is different than Mexico.”

“Mom, you know I have to go on this trip. I’ve been telling people for three years now. I have to. You know that feeling. I feel called to it.”

“Yes, I know. I know. ‘To whom much is given, much is required.’ I’ll plead the blood of Jesus over you every day. If anything happened to you—”

“Mom, I’ll be fine. And it’s not the seventies, I’ll have a phone and I can text you and get Wi-­Fi and call you all the time. When you and Dad did the walk, what did you do?”

“We found pay phones and called our parents once a week,” she said. “I know that me being paranoid is ironic because I did this to Meme. And I didn’t have a phone then. But that’s what happens when you become a mother. You become the things that drove you crazy as a kid. It’s the way God made it. To humble us, I think.”

“You don’t need to worry.”

“Well, you can’t go alone. I forbid it. Do you hear me, Jedidiah? I forbid it.”

I have no rebellion in me. If my mom forbade me from going, I’d be in a bad spot. I never did drugs. Never even tried them. That’s what “the bad kids” did, and that wasn’t me. Alcohol seemed trashy. Drugs seemed debased. To this day, it’s hard for me to break a rule. Especially if I’ve been told explicitly. This scenario has played out in my life a thousand times: A guard will say, “Sir! You can’t be in here. I’m going to need you to leave.” My friends will say, “He’s not looking, let’s go!” And I say, “But he said we can’t!” and I slump away.

I wanted to be a good boy, so I agreed to invite someone else along. Well, to be honest, before I had the chance to, he invited himself.

His name was Weston. He was visiting San Diego from New York three months before I was set to leave, and we’d met a handful of times. I was sitting in my office getting through e-­mails when he walked in. It was June, three months before I was set to leave. He bounced from desk to desk saying hi to people, and I could hear his voice and the exclamations of people who knew him and were overjoyed to see him. It’s that guy Weston, I thought. What’s he doing in California? He came into my office and grabbed me by the shoulder. “I heard you’re going on a yearlong bike trip. I need an adventure, I’m restless. And I want to be a character in a book.” He said, “You can write whatever you want. I have nothing to hide.”

There was something endearing about Weston’s narcissism. Broke and drinking expensive beer. Handy, clever, and tireless. Always on fire for a new idea, a new girl, a new food. He had held a ton of jobs, started businesses, started newer ones in the middle of starting new ones. You never really knew where he lived or where he was. He was tall, muscular, tattooed. Handsome in a way, severe in another. Women loved him. He loved that women loved him.

Why did he want the bike trip? I think he had burned that entrepreneur candle so hard, riding on the fumes of people believing in him, that he got singed. A long ride would be a reset. I thought there was a good chance he might get me in trouble or drive me mad, but maybe I craved that, so I said yes, and told Weston the plan.

We would start the trip at Jessie M. Honeyman State Park, halfway down the Oregon Coast—the same beach where my parents finished their walk across America. I wanted to walk my bicycle into the water where they had finished. I would pick up the baton.

A package came in the mail to my house. It was from my mom. I opened it up and it was a little pocket Bible. Leather-­bound. Beaten up, worn, with rounded edges. I opened it up and found red and blue underlining everywhere. Notes in the margins. My mom’s handwriting. And some of my dad’s, too. I recognized each handwriting style. Inside the flap was a note. “Jed, this was the Bible I carried in my pocket during the whole walk across America. I read it every night. When I was scared, God’s word was with me. He is always with you. I love you. He loves you.” It was holy to touch. A tangible anchor to my mom in her late twenties, my dad in his mid twenties, the God of the universe with them. Wow. I kept it in my pocket from that day forward.

As the day approached, the trip became the only topic of conversation at the office. My trick of telling everyone had worked a little too well. Everyone asked me about it. Are you ready? Did you learn Spanish? Have you been training? Nope. Nope. Nope. I had meant to learn Spanish. I even bought Rosetta Stone, which is like six hundred bucks. And I’d done it for a grand total of a week. Damn it. So typical. But here it was, the trip was around the corner. The spring and summer of 2013 disappeared, and August popped up like a jack-­in-­the-­box.

By the time Weston and I flew to Portland to start the damn thing, I was sick and tired of talking about the trip and not being on it. I wasn’t nervous. I was just ready to get everyone off my back. I was so afraid of being labeled a talker and not a doer. I boxed up my bike and some clothes and left the rest to buy in Portland.

Weston had virtually nothing. A small bag. I thought I was unprepared. Weston was so self-­confident, his lack of preparation came off like a deeply considered preparation in itself. “I don’t want to have too many things figured out,” he said the night before we flew out. “I’ll buy a bike on Craigslist when we get there for a couple hundred bucks.”

“Are you sure? What if there aren’t any?”

“There will be. There’s bikes everywhere. And if not, it’ll work out. Gotta trust the universe. If one door closes . . . ya know?”

“Well, yeah, that’s cool. But we do need to leave on the twenty- ­eighth.”

“Don’t worry, brother. I got this. I like that you worry. I like that you have a bike and extra gear and stuff. I got this.” He was so confident, it made me wonder if I was the one doing this the wrong way.

We woke at 6:00 a.m., and drove to the San Diego airport to catch a flight for Portland. I checked my bike and watched it disappear on the conveyor belt. I paid fifty bucks because it was overweight. Weston just walked on.

Table of Contents

Author's Note ix

The Itch 1

Part 1 West Coast

Chapter 1 The Plan 13

Chapter 2 It Begins 22

Chapter 3 The Coast Is Clear-Northern California 34

Chapter 4 The Temptation of Home-Southern California 55

Part 2 Mexico

Chapter 5 Crossing into Baja 65

Chapter 6 Some Background As I Lose My Mind-Baja and My Childhood 91

Chapter 7 Cartels and Coconuts 106

Chapter 8 The Cathedral Sits On the Temple - Mexico City 121

Part 3 Central America

Chapter 9 What Happens If I Go Home?-Oaxaca and Christmas 137

Chapter 10 Harry Devert-Panama 161

Chapter 11 A New Continent-Crossing to Cartagena 165

Part 4 South America for the Most Part

Chapter 12 Cocaine and Cute Little Mushrooms-Cartagena and Medellín 175

Chapter 13 God on the Trail-Medellín to Salento 188

Chapter 14 Sex Hotels and Here Comes Mom-Call to Quito 200

Chapter 15 The Coldest Night-Quito to Cusco 216

Chapter 16 Empire Falls To Empire-Machu Picchu 232

Chapter 17 New Blood Into Bolivia-Bolivia and Argentina 253

Chapter 18 All By My Argentina-Solo Down Argentina 259

Part 5 Patagonia

Chapter 19 Entering the Holy Land-Mendoza to Bariloche 275

Chapter 20 Alone In God's Most Obvious Work-The Carretera Austral 290

Chapter 21 Mom and the Mountain-Torres del Paine 299

Afterword to the Paperback Edition 317

Acknowledgments 319

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