I am currently in Newport on the coast of Oregon, staring out the window at the ocean. There is an orange kite hanging in the sky. It has a long tail that is fluttering in the wind, but for a solid minute now the diamond of the kite body has stayed motionless in the sky, almost as though it were pinned there. From my angle, I can't see the string or the person holding the kite. Just now, the unseen person has decided to let out more string. The kite at first shudders, like a sick dog trying to back out of one of those horrible neck cones, and then it proudly accepts its new directive and rises to an incredible height. I can't see the ground, so I can't estimate how high it is, but it has now risen out of view.

To sum up: I am looking out the window at a person flying a kite, but I can't see the person, or the kite, or the string. I see nothing.

I came to the coast because I want to learn how to sail. A young man named Daniel is my teacher. He is working in an Irish pub in town and helping his friend prepare his 29-foot fiberglass full keel sailboat for a long sea voyage. In a week, the two of them are going to sail it to Hawaii.

Last night he walked with me along the shore and went over the basics of sailing with the patience and enthusiasm of someone who just recently learned it all himself. He talked about the golden arcs on the Earth that give you the most direct line to a destination. He explained the logic of referring to "port" and "starboard" as opposed to trying to say "left" or "right" when people might be facing different directions. He has a great way of explaining things in a direct and respectful way that doesn't feel like a lecture. He showed me how to juggle three balls by standing in front of a wall to ensure that everything I threw was on the correct plane.

This morning he gave me a very old copy of Rilke's Letters to a Young Poet to read while he went to work. The covers are torn off and some pages are missing. In it I read, "But in every sickness there are many days when the doctor can do nothing but wait. And that is what you, insofar as you are your own doctor, must now do, more than anything else."

Any time I'm about to travel my mind goes to all the infinite things that could go wrong: the flights I could miss, the unexpected expenses, the places to stay that could fall through. Seasickness and nausea come from a fear of instability or discomfort. I've discovered that the fear of discomfort is much worse than actual discomfort.

It's when I actually embark on a trip that I realize that every moment is something finite and manageable. Even if it's uncomfortable, it's uncomfortable in a way that I can identify and deal with. The unknown infinite horrors my brain can imagine are always worse because I have no way of solving them. One time when I had an early morning flight from LaGuardia and nowhere to stay the night before, I walked around Brooklyn with my bags all night. It wasn't cold out and I could just listen to Smiths songs and visit 24-hour bodegas and linger in the chip aisle like I was making some monumental decision. Staying up all night isn't hard if you've decided it's what has to happen. It's almost a relief in some sense that an actual tangible problem is in front of you and you know the shape of it and can confront it, as opposed to dealing with all the possible bad things.

Rilke also wrote, "Perhaps all the dragons in our lives are princesses who are only waiting to see us act, just once, with beauty and courage. Perhaps everything that frightens us is, in its deepest essence, something helpless that wants our love."

I dedicate my life to learning—as I think everyone should—in order to eradicate fear. The unfortunate aspect of formal schooling is that it taught me that learning is boring. I have spent my adult life learning that learning is not boring. Learning is taking a thread of something you are interested in and pulling on it to see where it leads, and if that thread crosses another thread that excites you even more, then to go off in that direction and trust that you are ultimately heading toward a really intriguing ball of string somewhere. It's not that you will ever really find that ball of string, but you want to keep pulling on threads to see where they will go. The greatest thing a teacher or institution could do would be to provide a student with some fundamental blocks of basic knowledge as a way of engaging with the world, and slowly turn those blocks Vanna White-style to reveal that they aren't blocks, but rather secret passageways that lead you down exciting corridors, and that nothing about learning is boring.

What we can learn by learning to sail is a certain patience and humility to say simultaneously that our fate is dictated by the winds and the water, yet to take some fundamental control over that fate and make micro adjustments that get us where we actually want to go, even across an entire ocean.

It's investing in skills and knowledge that are older than your grandfather. That is usually a good place to look to put your intention when you are otherwise feeling ungrounded or rudderless. When you can find arcs that extend beyond your own lifetime—long smooth arcs like the fiberglass keel of a sailboat—your mind can submit to the great unspoken grace of the enduring world.

For a long time I thought music was that thing that would ground me. I still believe that in some ways, but what I have been caught up in lately is this: I feel that I am good at writing a song, at being able to play guitar, at all the various skills that go into making a record, yet for many years I have had the strong feeling that I have failed at music. I've never sold more than a thousand copies of any album. There isn't one city in the world where I can play a show, where anyone will be there to listen.

Only in the last couple years have I been able to remind myself that I haven't failed at my art; I've just failed at being a capitalist. I've also decided that I don't really mind being bad at capitalism.

When I was in Bogotá, I went to a small bar to watch a guy named Gabe play music. My editor Michael put me in touch with him, describing him as a "talented musician, total weirdo, worth your time."

I walked in the bar just as he was about to start playing. There were maybe three other people there. Gabe was holding a kora, a West-African instrument that has a globe at the bottom, a long neck, and a bunch of strings connected to leather straps. He had a small tambourine tied to his knee that he could shake rhythmically. He played his first song, and the notes cascaded out kind of like a harp with unique patterns and rhythms. He could play the rhythmic part and then solo over it, and with the tambourine and his voice the band was complete.

I had seen people play the kora before, but always in traditional ways, very respectful of the heritage of the music. Gabe was writing his own songs on it and singing "Summertime" in Spanish. Gabe's dad was at the show visiting from Chicago. I glanced at him out of the corner of my eye and discerned the disappointment of a parent who was wondering how his child was ever going to survive if he was playing shows in Colombia on some strange West-African instrument to four people.

After Gabe finished his set, I turned to his dad and asked, "What do you think?" I was asking what he thought of Bogotá, but he thought I was asking about Gabe's music and he said, "I think he's a starving artist."

There are a couple things I hear in that statement. One of them, of course, is a deep love of a father for his child. He went through the sleepless years of creating this human being and worrying about his child's survival. It's hard to turn around and accept that you can't always keep your child from harm, that he will be doing things that look uncomfortable.

But the other thing I hear in that sentiment is a type of abdication of humanity in favor of capitalism.

The life I found myself after years of playing music was what I would refer to as a lottery mentality. I was living in Portland, a city where there are many musicians full of talent and hope that their efforts will get them somewhere. There is unfortunately no middle class in the music business like there was a generation ago when you could be a competent band who could provide a night of music at a bar and get paid decently. Now you are either one of a rare few to have a meteoric rise to great success, another several hundred who have found a niche through hard work and luck, or you are one of the millions who work in near obscurity and poverty. There is no shame in being obscure, but there is a shame in living your life under the constant delusion that everything will be better once your ship comes in. As John Steinbeck wrote, "Socialism never took root in America because the poor see themselves not as an exploited proletariat, but as temporarily embarrassed millionaires."

I found myself, along with many of my friends and peers, constantly dissatisfied with my level of success, but still determined that things would improve in the next six months. That started to shift when I finally asked myself honestly, "What if it will never improve? What if I will never sell more albums, play to bigger crowds, have any bigger success?" If the answer to that question was anything short of, "I'm perfectly fine with that," then I realized I needed to reorder my priorities.

It turned out I wasn't OK with my life as I was living it. My happiness was unduly affected by the lack of a positive Pitchfork review of my album. I played music because I loved music and my dreams of success were shaped by the examples I saw around me, and not achieving that success naturally felt like a failure. Not just that, but it felt as though I had been wrong about what I thought I loved, like I had been caring deeply about a woman who turned out to be just a pillow on a mop handle.

So I had to ask myself, "What parts of my world can I control that reliably make me happy?" Record reviews and show attendance aren't things I can actually control, but learning new skills is. That led me to decide to live in New York for a while and study ballet music and opera; it led me to taking drum lessons to understand rhythm in my body and not just my mind. I wasn't just deferring my happiness to some imagined period when the reviews came in and I was at the level of success I thought I deserved. The more musicians you meet the more you realize that almost none of them are at the level they think they really deserve, no matter how big they are.

All of that led me eventually to Bogotá to write about music, and it led me to watching Gabe hold that strange instrument that was half-furniture and half-conversation piece and seeing him make really wonderful sounds from it. Sitting next to his father, wearing his light beige fatherly jacket, I knew before he even said a word what he would say, but now I could identify that he was the one who was unhappy. Any time you live a life according to what you think someone else wants from you, whether that's your parents or society or God, you are going to come up disappointed. Because really those voices are just in your own head. That doesn't mean that you have to run away to Colombia and play the kora. It might not involve running at all, or music, or art, or anything.

I've decided if I'm investing my impression of my value judged by capitalism or art, I am going to choose art. That's what I always wanted; I just let myself get convinced of other things along the way. If I opened a restaurant and created dishes that I really believed in and put all my love into, I wouldn't look across the street at a McDonald's and despair at how much more popular that restaurant was. I would know that even though we were both ostensibly making food products for people to eat, we were in completely different universes, and I couldn't possibly gauge my success against theirs. It's the same thing if I see a band become successful, and I wonder why that same success doesn't happen to me (which by the way is what every single musician spends 50 percent of their time doing.) When I first started writing songs, all I could dream was that I could make one person somewhere feel not so alone or improve one person's life. I can be sure that, at the very least, that has happened, and so anything I might want beyond that is just a matter of scale. It's like making one great dish and then thinking, "How can I get this into the hands of every person on Earth?" The things you'd have to compromise to make that happen change the original product. Capitalism tells us that music you made for one person should be played for ten thousand when we know that it doesn't necessarily work. Some music is made for that large arena, and some isn't.

When I actually made it out on the water with Daniel in Newport, the ocean was calm—as calm as you could expect the Pacific Ocean to be. It was one of those overcast days on the northern coast where sky and sea are gray and wet, and once you get out on the open water you can't see the land anymore. Those environments where you feel that you're in a Homeric poem and someone has cast a spell and put you in an in-between world. I felt OK for about five minutes, and then I started to get really seasick. I had a few seconds to plan where I was going to throw up. I tried to lean over the railing, but didn't get all the way. After puking, I stared at the half-digested eggs and toast Daniel had made for breakfast sitting on the side of the railing for a few seconds before a wave came and took it away. After a year of intense emotional churning, it was actually nice to have my insides come out, to just look at it and say, "Well there it is, the source of all this restlessness." It felt satisfying, but it didn't feel good, and the sickness didn't go away after throwing up or even when we got back to land. On the water, I was able to meekly help with a few lines, tie a few knots, but mostly I was just ballast. I felt bad that all of Daniel's training had been spent on me and I couldn't even handle the calmest day of the year on the Pacific. Maybe the more you learn about sailing, the more your fear dissipates and the seasickness becomes less of a problem.

I did see Gabe and his dad again after that night in Bogotá. Gabe invited me to come visit him and his girlfriend and new baby in the village of Tunja, high up in the mountains outside of Bogotá. Gabe's dad was there, too. We went out into the town square one night, and as it was just past Christmas, there were flashing lights everywhere with little booths offering different treats. There was one kiosk made out of recycled plastic bottles that had a projector casting animated pictures on the ground, and little kids would try to jump on the images thinking they could grab them and keep coming up empty over and over again, but laughing all the time. As I was watching those kids, I heard a strange sound behind me. I looked to back to see Gabe facing his father and staring intently into his eyes. Gabe's dad was slumped in Gabe's arms and making a sound I've never heard a human make before. It was the sound of the body as a malfunctioning machine. I went over to help but didn't know what to do. He kept making that horrible sound, the worst snoring you've ever heard mixed with a security system failing. I thought that I was watching someone die right in the middle of town square on that beautiful night.

Gabe kept saying, "You're OK, Dad. It's OK." It turned out that Gabe's dad had epilepsy, and a combination of the flashing lights and the altitude might have set him off. I found out later that he had these fits as often as twice a week, and one time it happened on the platform of the L train in Chicago and his body fell on the side of the train as it sped by, bruising and breaking his arms and legs.

Once I knew he wasn't dying, the image of Gabe holding his dad in his hands looked tender to me, especially after his dad had bemoaned his son being a starving artist. Often people have the harshest criticism for other people who are claiming the freedom that they were afraid to claim for themselves.

I knew that Gabe wasn't the kind of guy who would ever change just to please his dad. He had lived the past three years in Bolivia, and when I asked him about it he said, "It's amazing. There's just nothing there. You can live on just a few dollars a week."

I kept thinking of the way he described that country. "There's just nothing there." He said those words with a wonder in his eyes about something that most people would be bored with.

The next night Gabe had a gig and at the last moment he asked me to back him up on drums. Gabe knew plenty of crowd-pleasing Colombian favorites: "El Año Viejo" and "El Ultimo Beso." I barely managed to keep the rhythm together most of the night struggling on a foreign instrument in a foreign town. Halfway through the set, he started to play a Spanish-language version of "I Will Survive." I steeled myself in the long intro buildup to the song, preparing to bust into a solid disco beat and keep it going until the song ended. I remembered the lessons from my drum teacher: If you put your body inside the rhythm of the music, if you move with confidence, there is no chance of a false step.