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. Because new places require new learning. It forces your childlike self back into action.

Every second has value.

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.

The factor that I overlooked was the finiteness of time. This concept is invisible to a child. Kids may know logically that they will one day be old, but they can’t feel it. It sounds like a rumor.

Time became visible. Each choice I made began to feel more and more final, as if every choice was the death of all the others. Millions of doors were locking behind me as I passed them in the hallway. I felt that age thirty—adulthood—was coming like winter.

The life before had happened to me as childhood happens to everyone. The mark of adulthood is when we happen to life. Thirty years old. I was now an adult, with or without my consent, and adults are responsible for their lives. I wasn’t going to become someone I didn’t choose to be.

We have a policy of no more than three exclamation points in any e-mail. And you have five in your greeting of ‘hello!!!!!’ That’s not acceptable.”

I’ll die if I work here. If they don’t fire me first.

hating work and therefore buying things, a house and a nice car, and having kids and sending them to private school. Raising them to chase their dreams, and lying with my life. That frightened me. I told my friend yes. I’d figure out how to make money later. For now, I’d be poor and happy.

I was reactive. I didn’t feel like an autonomous soul. I felt like a pinball.

Try it and then try something else. Sure, that works for a while, but sooner or later, that’s not cute anymore. You can’t keep jumping ship.

When you don’t know what to do, you travel. You go out and see. You have to rattle the bed, shake yourself out.

I was holding tight to the narratives of my youth like treasure. But with hands full, I couldn’t receive anything new. And I couldn’t see that I was clutching both treasure and poison.

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.

As I fell asleep, I thought of all the things I was leaving behind. My comforts. My expensive coffee and craft beer and back-porch hangs with my friends. My routine and my life. I knew it wasn’t forever, but it felt like it. What if my friends went on without me? What if my absence revealed that I was never really necessary? What if no one notices I’m gone?

“When you clip in, you will fall. Several times,” Collin said. “So just expect it. That way it won’t hurt your pride when it happens. Everyone falls.”

I wanted to physically discover the world, the old-fashioned way. To cross over mountains to see what was on the other side. To hear languages I’d never heard. To take the photographs from National Geographic and put them out in the weather of human imagination.

It’s no more dangerous now, it’s just the fear has changed.”

I would be stripped of what made me feel safe to make room for something else.

Again, the serendipity of some of this was not lost on me. It was just like the bees. Was God sending me signs to make me feel safe and good? I don’t know. But it felt like it.

The permanence of pen on paper means something. You say it, and it’s there, and if you change your mind, the scribbled-out words are still there—no pretending you’re perfect.

I like timeless things, old things. They’ve made it to the modern age and taken on a meaning larger than their intention.

Darwin and Steinbeck wrote alone by hand in leather-bound books that only later found an audience. Still, they wrote as if to an audience, with the presumption that someone, one day, would read their private work. Is this so different from what I was doing on Instagram? It feels cheap to make the comparison, but maybe it’s not.

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.

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.

Too much movement, and you can’t see minor changes. Until it’s too late.

I could see I had a lot of things pulling strings in the shadows, making decisions for me just outside my view.

We both laughed hard at the release of being allowed to hate the adventure we were on.

we felt like cheaters but we didn’t care. Who were we cheating? We made the rules.

Human beings have little capacity for sustained horror. I think our minds need to play to survive.

For the freedom of seeing new things and not knowing what was next.

I wanted a taste of home: some bougie hipster coffee.

Because I wanted to.

I wonder how many millions of relationships are alive because of this, avoiding conversations.

She would ask me the same questions over and over with different words, as if the act of talking was the goal, not the exchange of information.

“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.

It was like a squirming thing under the covers on a bed. It made me remember why I liked living in California, free from the odd feelings of family obligation and love. Somewhere inside my relationship to my family was the root of fear, fear of my sexuality, the root of my faith in God. My friends in California and the life I’d built out there were all on top of this small group of people that made me.

“No, I love these idiots. This mess is what made me. I just need to control my doses. It’s easy to overdose and get sick.”

I was also reminded of what I was looking for. A shaking-off of that film over my body I feel at home. Of confusion. Of self-loathing. Of constriction. I had to peel it back and see myself clean of what I had been told.

“Do you think we’ll get the excitement back? For biking?” I said. “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 guess that’s the thing,” Weston said, an aside to himself. “This experiment with money. The universe will provide, but it’ll cost you your pride.

“Let’s just believe it’ll work out,” Weston said.

It didn’t feel like life in paradise. It felt like poverty tourism.

“I’ve been thinking,” he said. “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?” he said. “I’m not sure.” “Addiction is a term people use to label and categorize and dismiss. It stops you thinking about it. Addiction implies that the thing is bad. It’s all made up. I just want to think critically.”

I had decided South America was the land of Indiana Jones adventure and sacred mountains and my spirit-quest revelations. I expected it, and so, now biking it, I felt it coming, I felt it promising me everything.

I am a nomad, I thought. I am comfortable in this homelessness. This at-homeness on the road.

a faith system that is the norm and the majority, but pretends it’s a victim and the underdog.

Those hats. They love them. I kept asking people why, and they didn’t know. I found that curious. You live in a country peopled with this interesting culture, and you don’t know why they wear their very distinct costume? Then I thought, why do some Native Americans wear suede coats with frills, or headdresses, or why do some black people wear picks in their hair or do-rags? Why do businesspeople wear ties? I have no idea. I’ve never asked.