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

by Jedidiah Jenkins

I have learned this for certain: if discontent is your disease, travel is medicine. It resensitizes. It opens you up to see outside the patterns you follow.

But as you get older, and the patterns become more obvious, time speeds up. Especially once you find your groove in the working world. The layout of your days becomes predictable, a routine, and once your brain reliably knows what’s next, it reclines and closes its eyes. Time pours through your hands like sand.

This kind of attention is natural to a child. To an adult, it must be chosen. The trick is: knowing when we are in fact adults, and when attention is asleep.

But the big fancy adults preach the opposite as well. They say, “fall in line” and then, in the same breath, “think different, take risks!” We are told, “follow your passion” and “stay hungry,” at every commencement and graduation speech. This mixture of school and risk is the holy cocktail of American ideals, and for those rare beacons of exceptional success, it turns their life stories into fables. But for ordinary folks, it is a difficult road to walk. Be sensible, but be wild. Be ordered, but be free. Be responsible, but take risks.

It often dawns too late that we have only one life, only one path, and the choices we make become the story line of our lives.

I looked back on my twenties and realized that every time there was a crossroads, I took the first and safest path. I did just what was expected of me, or what I needed to do to escape pain or confusion.

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 try to be too fanatical about it, you’ll spend more time stressing out and less time seeing a place for what it is.”

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.

As we entered California, it looked exactly like Oregon—another reminder of the arbitrariness of most human boundaries.

I tried to get more intentional with my journaling. It hurts to write by hand if I do it for too long, which pushes me to keep my language tight and right.

There is a weird paradox in trying to live a meaningful life, one you will talk about and tell about. There is the present experience of the living, but also the separate eye, watching from above, already seeing the living from the outside.

I’m not sure any of us are at our best living in paradise.

The muscle that knows routine takes time to be reprogrammed,

People love to blame a place for their own failures. Los Angeles is the king of this. So many people move here to chase a dream, or to escape the cold, or to escape their family. The city is supposed to be the answer to their discontent, to whatever it was that rejected them at home, and in their mind, simply having the bravery to get out west deserves fanfare. But once here, they find that no one cares about them as much as they do.

I learned the difference between dreams and goals. Each of us has a mash-up of talents and experiences and potential that plants something in us, and becomes a dream. A dream of being a creative, or an executive, or a father. A dream is the myriad ways we could be fulfilled in life using our talents to make beautiful things. But then there are goals. Goals are specific guesses at what we could do or become to fulfill our dream. Dreams are like a compass that points in a general direction, and goals are the islands in the ocean along the way. Goals are just guesses at where to make a home, and when they aren’t right, we try another. It isn’t a death, and it doesn’t negate the dream.

Miguel got me thinking about how strange it is to be born in a country whose influence has spread around the world like an infestation. The world’s hunger to speak English is emblematic of this. Some cultures welcome our films, television, and music, or feel drawn by the prospect of money and power. Others resist. Either way, my culture is the most dominant on the planet, and I benefit from that.

This shitty situation had given us the opportunity to receive the kindness of a stranger, to see the life and home of a person we’d have never known. I lay there thinking back through my life—how much energy I put into planning, trying to guarantee my independence, but how so many of my best memories have come from the times where I needed help and received it.

This happens a lot with people who espouse idealism. We want to feel better about our mediocrity, so we look for the holes.

“I feel like we’re so lucky to be on this trip and people wish they were doing it and not stuck at a desk job, but damn, the adventure wears off, doesn’t it? I mean, I’m not ready to quit right now or anything. But it feels good to admit it isn’t one long string of euphoria.” “Fuck, it feels good to admit that,” Weston said in the darkness of his hammock.

I couldn’t give up on my global optimism. I’ve always believed that the world is far friendlier than it is not, far more loving than hateful. Fear is like a thorn in your foot. It may be proportionally small in relation to the body, but it hurts and demands attention and everything halts until the thorn gets pulled. But dammit, I felt stupid, feigning my optimism here in Nexpa. Playing it cool. Wondering if I’d be shot by accident or on purpose. There is truth in a mother’s worry. There is also exaggeration and unfairness. If I die, she wins, I thought. If I live, I win.

Human beings have little capacity for sustained horror. I think our minds need to play to survive. Permanently serious people always look so tired, maybe because they are fighting an emotional battle that eats the body alive.

I read that when Tolstoy was young he wrote in his journal, “I am twenty-four years old and I have still done nothing…I am sure it’s not for nothing that I have been struggling with all my doubts and passions for the past eight years. But what am I destined for? Only time will tell.” I was thirty years old reading this, sitting by a river in Mexico, wondering what I had done with my life. I knew it wasn’t for nothing that I’d been struggling with all my doubts and passions for the past twenty years. I had dipped so deeply and completely into my faith, into my love of God, or who I made God to be, and what the people around me said He must think about everything. I knew it was not for nothing, but what, I didn’t know. I just knew it was somewhere in me, and I needed travel to shake it out. I needed to see different things to remind me what I was, in contrast to what I already knew. To see clearly what I had become.

In a moment, my thoughts were beyond the party, floating above us. “Ever at war with your vices.” It didn’t say “let each year have you conquering a new vice.” No. It wasn’t about winning. It was about fighting. Continuing the project of improvement. The intention and effort was what built character. Not success. That changed a lot of things for me.

In many ways, I’d exchanged an old routine for a new one. No mind-reshaping epiphany had come, and I didn’t feel like it was on its way.

You know someone best by traveling with them. When someone is outside their comfort zone, when they are hungry or exhausted, and when money is involved, you see the sides of them that are often covered up in social niceties.

“We have to choose it. It’s like a marriage. The honeymoon’s over, and we can jump ship or we can choose to love the one we’ve got, and make it fresh.

“I dream, I search, I love, I live.” Sure, it was cheesy, but he seemed to really be living. He seemed rungs ahead of me. Less confused. So full of discovery that discovery itself had become a religion. I felt like I was sitting here, hunched over in a tangle of feathers, while he was flapping his wings over the world.

Harry Devert’s Instagram posts and blog had one sustained theme: Human beings are lovely and kind. Each story testified to the kindness of strangers, the beauty of travel, the universal goodness of humanity, and the freedom of deciding to ignore fear and trust people.

“What if everyone is an addict and everything is a drug?” “Weston, do you ever turn your brain off?” I said. “Some things that we all accept are actually addictions. The Internet, we’re addicted to it. Our phones, are you kidding? The dopamine hit of checking your phone. We can’t function without them. Notice how these five days on this boat…no phones, no access to the outside world. There was a withdrawal period. It was weird, right? Everything is a drug. Coffee. Caffeine. Sugar. Sugar is in everything. It’s all drugs. What does addiction mean? Can we choose or help our addictions?”

“What’s the difference between being addicted to something and wanting to do something because you love it?”

It is astonishing how ideas can change an experience. How we can be in a beautiful forest, on a hike through verdant beauty, but if someone told us that the forest was the site of a brutal massacre, the entire hike would be transformed. It would turn ominous and sad.

Then—I feel it. A widening. A tingly slowdown of color and light. I hear sounds, as if I were a wolf. Sounds are isolated, far-off sounds, and feel very close. I don’t feel drunk or high, this is different. I don’t feel dumb or slow. I feel like myself, just…heightened. I feel what Weston had told me about: that nature would take on special holiness. I feel an intense love of it all. I pull out my pen and start to write. I want to push my face into the mountain. Not the one I’m on. The one far across the paradise valley that I could never reach. But the birds see it, and every mountaintop is just another stone poking out of the stream, hopping across. The birds have so much to say…

think about how badly he wants the world to make sense. How it tears him up, so he tears through ideologies, testing them with all his might.

How can you enjoy the day if you’re dismantling the world and the people around you piece by corrupted piece? I remembered the joke “love minus distance plus time equals hate.”

Your friends still love you. They haven’t forgotten about you. When you see them again, it’ll feel like nothing has changed.

Even after all this time, The Sun never says to the Earth, you owe me, look what happens with a love like that, it lights the whole world.

Traveling alone, you get to be whoever you want. I don’t mean lie. I mean you get to be a blank slate. You can’t leave behind your skin color, or your height, or the handsomeness or homeliness of your face. But you can leave your story behind. If you’ve broken hearts, the new place doesn’t know. If you’ve lost trust in people and yourself, the new place doesn’t know. If everyone thinks you love Jesus, but you never really have figured out what you believe, the new place doesn’t care. It may assume you have it all tied nicely in a bow. All your thoughts and histories.

Setting myself free, when and if I found myself alone. I was in a foreign place, far from any watchful eyes, from anyone who knew me. The invisibility. It made me realize how much of decency is built through community, through other eyes. I’d forgive myself just about anything if I felt anonymous.

Life can feel effortless, like you’re carried along by an unseen force. Or it can feel like you’re in a losing fistfight with a brick wall. It all depends on which way you’re headed.

As much as our relationship confounded me, I always wanted to celebrate with her. I couldn’t put a finger on it, but I knew that my deepest wounds were the place of my deepest meanings. And she was ground zero. My salvation was somewhere inside her.

It isn’t that I wasn’t thankful. It’s that I felt so bound up in my unknowing that I couldn’t figure out who to thank or who to curse.

It was sunset. 11,700-foot Fitz Roy showed itself through shifting clouds. I had cycled to Patagonia. I drank a beer, feeling proud but calm. I was simply done. Like the last grain of sand dropping in an hourglass, my experiment in time ended without a sound. I never got on the bike again.

On that bus, I had a lot of miles to stare out the window and think about my journey. About expectations. About destinations. I had wanted my spirit quest to answer questions for me. More than that, I needed it to reveal my questions to me, then answer them. What a burden to put on travel, which in itself is ignorant and indifferent. It becomes so hard to just enjoy the thing as it happens. We make the journey about arrival, not travel. We are so goal focused. We are the dog that won’t stop paddling as long as he sees the shore. But, man, my shore had been hidden by the fog for so long. Of course, goals help us get a lot done. But they often remove our attention from the experience to the achievement. When we arrive at the goal, we think, then we will be happy. When we finally get there, we can celebrate and have fun. When I get that job, I’ll be fulfilled then. When I get married, I will be happy. The Eden we pine for is not under our own feet or bike tires, but over the next mountain. I had crossed the mountain. I was in the Eden of my dreams. I had a couple weeks left in the adventure of a lifetime, but I was here. I had arrived. Now what? I suppose I’d worked through some things on the road. My faith had gotten rearranged, the puzzle pieces disassembled and spread across the table. Not put back together, but not a total mess either. I guess I did feel a warm direction, a positive pulling toward something else.

Thanks to him, I had come to realize that there were doors and rooms in the house of my mind that had always been there, but had been boarded up. He’d kicked some of those doors open. I had peeked through, broken rules, walked down dark hallways. And the house, even in its mystery and darkness, was still my home, and surprisingly still felt like it.

Yet now, at the end of the trip, I felt a dull melancholy. The way DayQuil can mask a cold, but leave you with a muffled head. I was excited, sure, but I was tired. I wondered if old age felt like this. If the end is not a triumph and fireworks, but a simple, quiet arrival. A beer in a pub and wondering what it was you had wanted so desperately. Looking back at a complex grab bag of lessons, but seeing no through line. Feeling pride of accomplishment, as I did now, but struck by your own cheating and laziness. And finally you take a cosmic bus to see your mother.

Maybe my dad said something to trigger it, I don’t know, but for the first time, it dawned on me that my mom would one day die. The thought bulldozed my mind and knocked everything over. I can remember exactly the bend in the road where I thought it. Mom would die. I would be without her. It felt like a terrible injustice. I remember turning my face to the window so as not to be noticed, pretending my sniffles were allergies.

Time didn’t quite move like I’d thought. I had wanted to slow it down. I wanted to be aware of every moment passing, in reflection and contemplation. I wanted to leave my office life in order to feel time passing in some more holy way, holding it in my fingers and studying each minute like a prayer bead. But that isn’t how we experience life. The first miles in Oregon, I had been self-conscious in the extreme. I had felt my knees and hands and breath. On our bikes, Weston and I rushed through the pungency of sea foam and evergreen, crazy with euphoria, sure the newness of it all would be eternal. But then we slid into living the trip, and my awareness dulled into routine. I had been reborn into a different life, a different normal. The bicycle, the camping, the two-lane highways, the people and cultures had become patterns I could predict. I had wanted slowness, but I got life.