“Well,” she said, “it seems like you used to do so much in a year, and I always wanted to include all your news. But this year, it just seems like you haven’t been doing very much, so I figured a shorter note was in order.”
I squirmed in my chair and readjusted my napkin. My mom — maybe like all moms — has a special way of saying just the thing that’ll hit your most vulnerable spot. She’s right — this year, I haven’t been doing very much. I’ve spent a lot of time wandering into churches, reading old journals, watching YouTube videos, and staring out of windows, but very little time making any work. I’ve been feeling really stuck, unsure about what to do next, and struggling with a lot of self-doubt and confusion.
After dinner, I walked across the street to the Lincoln Center fountain, and I sat on the granite slab next to the water. The night was dark and cold. Operagoers in tuxedos rushed to get taxis. I could feel the black stone below my body. I looked at the city sky but I couldn’t see stars. I turned my head to look at the water. The columns of water were moving up and down in some kind of pattern, but I couldn’t tell what it was. Sometimes the columns of water were tall, and moving up and down within their tallness. Other times, the columns of water were low, and moving up and down within their lowness. The columns of water were never not moving.
I thought about stuckness, and about where I lost the flow. I remembered other times in my life I’d been stuck, and how the stuckness always eventually passed. I thought how life is a lot like that fountain, with its columns of water moving up and down, and how the low points are actually thrilling because the high points are about to come back, and how the high points are actually terrifying, because the low points always come next.
I thought of my life as a series of chapters, and I realized that each time I’d been majorly stuck, it meant that a life chapter was ending, and that a new one needed to start — like the stuckness was always a signal indicating imminent change. My life has had a bunch of different chapters, each one beginning with the fresh-faced idealism of a new approach to living, and each one ending with a period of stuckness and a moment of crisis. I’d like to tell you about those chapters, in case they contain something useful for you.
I should say up front that I’m lucky to make a living mainly by giving talks about my work at conferences, companies, and universities, which affords me a lot of time each year to make new work (and to obsess endlessly about what that work should be). In Zen philosophy, they say that anything pushed to its extreme becomes its opposite. Sometimes I wonder whether too much freedom produces a weird kind of psychological paralysis, which is almost like prison. Still, obviously I’m grateful to be grappling with too much freedom instead of too little.
Paint — a foggy field in Deerfield, Massachusetts, with pages from my travel journals.
In high school, I was a total romantic. I had a field easel, and I’d stand around in meadows doing oil paintings while wearing a little beret. In college, inspired by the travel journals of Peter Beard, I kept elaborate sketchbooks filled with dead insects, pasted plants, ticket stubs, watercolor paintings, photographs, and writing. I made these books by hand and kept them for several years. At the same time, I was studying computer science in the early days of the Internet, and I felt a growing rift between the sober art of painting and the dizzying potential of the web. I couldn’t find a way to bridge these two worlds, and I started to feel torn — partly pulled into the future, and partly stuck in the past.
I’d graduated from Princeton but was still living in town, doing odd jobs and generally feeling bad about myself and unsure about what to do next. I took a trip to Central America and ended up getting robbed by five guys who put a gun to my head, beat me up pretty badly, and stole my bag, which contained a sketchbook with nine months of work. It was one of those odd moments in life that’s really traumatic, but which ends up being a doorway into something new. After the robbery, I gave up painting, stopped keeping sketchbooks, and resolved to use computer code as my new artistic medium. I wanted to make things that guys with guns couldn’t steal. Around this time, I received a one-year fellowship at Fabrica, a communications research center in northern Italy. I moved to Italy, and I started writing code.
Data — coding I Want You To Want Me in my old apartment in Brooklyn, New York.
I became obsessed with the potential of data to tell me everything I’d ever need to know about life. I could sit safely at my desk and write computer programs to gather vast amounts of Internet data, which I thought could finally answer timeless questions like “what is love?” and “what is faith?” with precision and clarity. With manic self-confidence, I pumped out project after project visualizing different data sets, pairing each project with a bombastic artist statement about how the work revealed insights about humanity that had previously been hidden.
There was We Feel Fine (a search engine for human emotions), Universe (a system for deducing new constellations for the night sky), I Want You To Want Me (a study of online dating), Lovelines (a portrait of love and hate), 10×10 (a distillation of global media coverage), Phylotaxis (a visualization of science news), and Wordcount (an exploration of language).
My data visualization work coincided nicely with society’s increasing obsession with data-based reasoning, which was infiltrating nearly every aspect of our lives — from news, to sports, to finance, to education, to politics, to healthcare, to dating. Because of this, I got lucky, and had some early success. I got to speak at TED, got a commission from the Museum of Modern Art (MoMA) in New York City, showed my work at Sundance, appeared on CNN and NPR, and companies started paying me to give one-hour lectures about working with data. I quit my job, and spent all my time giving talks and making work.
I burned through projects and people, devouring a series of relationships that never seemed as interesting as my work. I was full of pithy insights about human emotion to spout at cocktail parties, but I started to notice that my data-based insights did very little to help my actual relationships. I began to grow suspicious of data. My insights felt increasingly superficial, and though they made me sound clever and witty, they didn’t do much to help me be kind. The world’s love affair with data was just heating up, but mine was cooling down.
MoMA commissioned the last data-based work I made: a project about online dating, called I Want You To Want Me. I’ve never worked harder on anything. For three months, I spent eighteen hours a day in front of a five-foot-wide touchscreen, poring over hundreds of thousands of dating profiles, and writing over 50,000 lines of code. I’d go for walks in the evening around my neighborhood in Brooklyn, and I’d look into restaurants at actual couples on actual dates, unable to imagine what they could possibly be saying. My mind was completely inside the machine, and I’d never felt more alienated from other human beings. I guess I thought the MoMA commission would somehow change my life, catapulting me into even higher echelons of fame and attention. But that didn’t really happen. The show went up, there was a big party, and then people basically went back to their lives.
I didn’t know what to do next. I went on some Internet dates, but it was hard to connect with anyone, and I just ended up feeling worse about myself. I started to get really depressed. I went down to Texas. I drove out to Marfa and saw the Marfa lights. I drove to the Mexico border and waded across the Rio Grande into a desolate Mexican town. I slept out in the desert under the stars. Being away from computer screens, I started to feel better. A sense of adventure and possibility crept back into my life. I’d meet strangers in diners, and it would feel good to talk to them. I started to feel human again. I liked the feeling of rambling around, getting into strange situations, and actually living life in the physical world. I decided to start making projects about the real world — where instead of using a computer, I’d do the “data collection” myself. I’d take photos. I’d shoot videos. I’d record sound. I went back to New York to get started.
Documentary — characters from The Whale Hunt, Balloons of Bhutan, and I Love Your Work.
Instead of trying to be the smartest person in the room, now I wanted to be the most interesting. Many people make choices to try to be better people — they take up yoga, they become vegetarian, they resolve to spend more time with their parents. Often, I use my work as a way to steer my life in a particular direction. I’ll identify something I want to change about myself, and then I’ll design a project to help me do it. In this case, I felt like I’d never really become a man. My childhood friends in Vermont were hunting deer, building houses, running farms, and being dads. I was just typing into computers, writing clever programs, and looking for praise. I wanted to change that. I wanted to live a bolder life, and I designed a series of projects to force me to try. I went whale hunting in Alaska. I traveled to Bhutan to learn about spirituality and happiness. I filmed the everyday lives of lesbian porn stars in New York. For each of my deficiencies (masculinity, wisdom, sexuality), I designed a project to help me confront it, which I hoped would help me transcend it. In a way, this worked. My life suddenly got interesting. People were curious. I always had outrageous stories to tell. I’d present these stories in intricate interactive frameworks of my own design, and I’d release them on the web. Again, I got lucky. My work with interactive storytelling coincided with society’s increasing obsession with “storytelling” in all of its forms.
Storytelling, which used to be a reasonably small niche populated by organizations like This American Life, The Moth, and StoryCorps, was suddenly everywhere. Every advertising agency was now a “storytelling agency,” every ad campaign was now a “storytelling campaign,” and every app was now a “storytelling tool.” Storytelling had gone mainstream and become one of those words — like “sustainability” and “innovation” — that’s so ubiquitous as to be basically meaningless. Yet through all this, I was riding the wave.
The World Economic Forum named me a “Young Global Leader,” citing my storytelling work. I was constantly being invited to trendy cocktail parties in New York. I was flying all over the world to give lectures. My life was moving very fast, but I began to feel like a fraud: I was wearing my stories like armor, telling the same winning tales again and again to laughter and praise, but never going deeper, and never revealing myself. I began to feel like a hunter, constantly chasing down the next story to win me acclaim. Since all my stories (like most documentaries) basically belonged to other people, I also began to feel like a thief.
One night, I hosted a dinner party for twelve at my apartment in Brooklyn. We stayed up till five in the morning and drank eighteen bottles of wine. My friend Henry stayed over, sleeping on the couch. At 7:00 a.m. a loud BOOM awakened us; the whole building was shaking. We rushed to the window to see that a car had crashed into the building; only its trunk was poking out of the hole it’d smashed in the wall. Smoke was rising from the hood. We ran into the street in our underwear, unsure if the car was about to explode (luckily, it didn’t).
I took the car crash as a sign to leave New York and find a new direction. I wanted to slow down. I wanted to simplify my life. I wanted to find balance again. I didn’t want to rely on other people’s stories. I didn’t want to be a thief anymore. Instead, I decided to hold a mirror up to myself and tell my own stories.
Autobiography — my cabin in the woods in Sisters, Oregon, watched by an owl.
When I turned 30, I left New York, bought a car, and drove across the country to Oregon, where I spent four months living in a little log cabin in the woods. I’d see another person about once every four days when I traveled to town to buy groceries. I started a simple ritual of taking a photo and writing a short story each day, and then posting them on the Internet each night. I continued this ritual for 440 days, and I called the project Today.
At first, Today was a wonderful addition to my life. I found myself becoming more aware of the world around me, more capable of connecting with others, and better at identifying beauty. I became obsessed with life’s “teachable moments” — the little things each of us encounters that might have a teachable value to others. I got good at spotting these teachable moments and condensing them into little narrative nuggets, so that others could digest them. I began to understand that principles delivered out of context will never be remembered, and that telling people the story of how you came to hold a given principle is better — so it’s like they lived through it themselves. I got obsessed with the potential of stories to communicate wisdom, but at the same time, I began to understand that really, you can’t teach wisdom — it has to be won by experience. Stories can alert you to the existence of certain truths, but you never really embody those truths until you reach them on your own.
I traveled from Oregon, to Santa Fe, to Iceland, to Vermont, doing a series of art residencies, living like a hermit, and continuing my daily photo project. More and more people began to follow along, until an audience of several thousand strangers was observing the intimate details of my everyday life. This began to be a burden. The project took on a performative quality; I found myself intentionally hunting down interesting situations, just so I could write about them that evening. I found myself plundering the relationships in my life for material, often with damaging consequences. I began to feel like a spectator to my own life, unsure whether to document it or simply to live it.
During this time, I fell in love with a young woman named Emmy. She was working at the art gallery in Vermont where I had a show. We only knew each other briefly, but when she chose to leave me for her ex, I was devastated, and for a couple months, I could barely get out of bed. This was probably the lowest point in my life. My daily stories around that time were brutal and strange, and my family and friends began to worry that I was in danger of harming myself. At that point, the daily stories were simply too much, and I abruptly decided to stop the project. I sent a brief email to the people following it, saying I wouldn’t be doing it anymore, and thanking them for their attention.
Within an hour of sending that email, I received over 500 responses from people all over the world, telling me how much the project meant to them, and thanking me for doing it. Most of these people I’d never heard from before. One woman in the UK said the project had kept her from killing herself, because it gave her hope each day to keep going. Many people said they’d never written before because they never knew what to say, but that my daily story was their favorite part of each day.
I never imagined that such a simple project — just a photo and some of my thoughts — could touch so many people so deeply. It made me realize that the most powerful things are often the simplest, as long as they’re made honestly and with a lot of heart. It also made me believe in the power of personal stories, so I decided to make a tool to encourage other people to tell them.
Tools — coding Cowbird in Siglufjörður, Iceland, under the aurora borealis.
I set out to create Cowbird, a storytelling platform for anyone to use. My dream was to build the world’s first public library of human experience — a kind of Wikipedia for everyday life. After making so many projects for people to look at, I wanted to make something for people to use.
I thought Cowbird would change the world. I thought it would become the anti-Facebook, harnessing a growing desire for substance, and that millions of people would use it. It was simple and beautiful, and brimming with detail, sincerity, and depth. I worked on it alone in isolation for two years, with monomaniacal certainty that people would love it.
During that time, the world changed. Storytelling apps became commonplace. Internet use went mobile. Tablets went mainstream. Geolocation emerged. I noticed these things, but I ignored them. I worked with single-minded focus on Cowbird, sticking to my original vision, which became increasingly out of touch with reality. By the time Cowbird finally launched, it joined a crowded field of storytelling apps (Instagram, Path, Facebook, Vimeo, Tumblr) with more to follow (Medium, Vine, Wander, Days, Storybird, Maptia, etc.). All these apps were basically the same — ways for humans to share photos, videos, and text — and this process began to bore me.
But I was living in northern California near Silicon Valley, and everyone urged me to do what everyone out there does, which is to start a company and raise money, so that’s what I did. I hired fancy lawyers for $850 an hour, founded a Delaware C-Corp, and arranged an angel round of $500,000 from a dozen investors, using a convertible note. This whole process felt icky to me, but I did it anyway — it was simply what everyone in California did. Right before we signed the paperwork, I had to fly to Spain to give a lecture.
For the first time in months, I had a few days away from computers and away from Silicon Valley. I wandered the streets of Barcelona, sat in cafes, and thought about the life I wanted to live. I watched old Catalonian couples walk hand in hand through leafy plazas. The women wore ankle-length dresses, and the men wore clunky shoes and fedoras. They walked slowly, said hello to friends, looked around at the buildings, and up at the trees. It was a world away from the frantic ambition of Silicon Valley — here it was just human beings living their lives.
A couple months earlier, a wealthy Internet friend had invited me on a sailing trip to the British Virgin Islands. One day, we visited Richard Branson’s private island. I was struck by Branson’s humility; even with all of his fame and success, he’d never stopped being kind — maybe that was his secret. It was interesting to see his life — the secluded tropical island, the flamingo colony, the giant tortoises, the lemurs, the bungalows, the sailboat races, the assistants, the phone calls, the beautiful people. This was the endgame of the money life, and it made me realize it wasn’t for me.
When I think about my own future, my dream is always the same. I’m living in a small beautiful farmhouse in a small beautiful town among a small community that values me. I’m living with a wife and kids I love deeply, and I spend each day making art and watching nature. My mind is clear and calm, I’m in control of my time, and I’m kind.
In a cafe in Barcelona, I decided not to take the investment money. In my heart, I realized I just didn’t want to run a company. I didn’t want to sit in meetings, manage people, market products, raise money, and send emails all day. Really, I just wanted to make small, beautiful things.
Getting unstuck — in my childhood bedroom in Shelburne, Vermont.
All we have in life is our time. People struggle after success. They hunger for fame, fortune, and power. But in all of these things, the same question exists — what will you do with your time? How do you want to spend your days? As Annie Dillard reminds us, “how we spend our days is, of course, how we spend our lives.”
In life, you will become known for doing what you do. That sounds obvious, but it’s profound. If you want to be known as someone who does a particular thing, then you must start doing that thing immediately. Don’t wait. There is no other way. It probably won’t make you money at first, but do it anyway. Work nights. Work weekends. Sleep less. Whatever you have to do. If you’re lucky enough to know what brings you bliss, then do that thing at once. If you do it well, and for long enough, the world will find ways to repay you.
This fall, in a toilet stall in Burlington, Vermont, I saw this scrawled on the wall:
“Don’t ask yourself what the world needs. Ask yourself what makes you come alive. The world needs more people who have come alive.”
If you’re doing something you love, you won’t care what the world thinks, because you’ll love the process anyway. This is one of those truths that we know, but which we can’t seem to stop forgetting.
In America, success is a word we hear a lot. What does it mean? Is it money, power, fame, love? I like how Bob Dylan defines it: “A man is a success if he gets up in the morning and gets to bed at night, and in between he does what he wants to do.”
We have these brief lives, and our only real choice is how we will fill them. Your attention is precious. Don’t squander it. Don’t throw it away. Don’t let companies and products steal it from you. Don’t let advertisers trick you into lusting after things you don’t need. Don’t let the media convince you to covet the lives of celebrities. Own your attention — it’s all you really have.
In the tradeoff between timeliness and timelessness, choose the latter. The zeitgeist rewards timeliness, but your soul rewards timelessness. Work on things that will last.
Inside each of us is a little 10-year-old child, curious and pure, acting on impulse, not yet caring what other people think. Remember what you were doing at ten, and try to get back to doing that thing, incorporating everything you’ve learned along the way.
When I was ten, I was writing words and drawing pictures.
Maybe that’s the path out of the stuckness. 
This post was originally published at Transom and is reprinted here with permission.