How to Deal with Failure

The pursuit of every goal starts out with the feeling of setting off to save the world. Everyone you meet hears about it. “It’s something I’ve always wanted to do, and now it’s happening.” Even though the future is scary and uncertain, the knowledge that you’ve overcome resistance and begun to work towards your goal makes you feel like a superhero.

You start to see some results. It’s a rush. The success-to-be feels more real, more attainable. You begin to imagine yourself as a person who’s already accomplished this goal. That goal slowly morphs into an essential part of your identity, even though it hasn’t even come true.

And then your fantasy smacks into an uncooperative reality. Failure. After months of work. After years. After a whole life (it seems). It’s like losing a part of yourself.

We’ve all been there a bunch of times. Careers, personal projects, relationships, friendships, new hobbies. They inflate like balloons in your mind and burst when they hit capacity. They fly out of your hands. They get ugly stretch marks and you “accidentally” let go, only to regret it later.

It happens.

So you messed up. Big deal. Literally every person who’s ever done anything has failed in huge ways. Shame is useless. The question is, how do you go forward from here in a way that’s meaningful and productive? Here are a few pointers:

1) Stop thinking in terms of “failures.” Call them “mistakes” instead.

“Failure” is a loaded word. It describes this kind of fatal blow to your identity we were talking about earlier. Feelings of failure do not come from having a healthy mindset when it comes to goals. They come from having unhealthy, needy, co-dependent relationships with your goals.

Goals shouldn’t be like crazy girlfriends who call you sobbing at midnight because they need attention. Goals should not become wrapped up in every part of your identity. You should never love a goal so much that you can’t imagine life without it.

Stop framing goals in melodrama and see things for what they are. Goals are not your purpose in life. Errors are not violations of your purpose, because life doesn’t have a purpose. Goals are nothing more than fun adventures that give us meaning. Things that go wrong along the way are just “mistakes.”

“Failure” is too much. It’s too dramatic. It’s not actionable. Save “failure” for special occasions, where a huge and essential system is truly, hopelessly, catastrophically fucked. Nuclear reactors fail. America’s public education system fails.

But not us. We make mistakes. And like Charles Munger said, “There’s no way that you can live an adequate life without making many mistakes.”

2) Rationally evaluate your mistakes

Calmly figure out what role you played in the creation of this undesirable outcome. Don’t do that next time. This is an essential step, which most people don’t take because they expect themselves to be perfect.

Peter Bevelin gives a great checklist for analyzing mistakes in Seeking Wisdom. So great I decided to include it, despite his use of a dirty word.

  • What was my original reason for doing something? What did I know and what were my assumptions? What were my alternatives at the time?

  • How did reality work out relative to my original guess? What worked and what didn’t?

  • Given the information that was available, should I have been able to predict what was going to happen?

  • What worked well? What should I do differently? What did I fail to do? What did I miss? What must I learn? What must I stop doing?

Once you’ve gone through this checklist and learned all you can, it’s time to…

3) Let it go already!

Be forgiving. You’re not alone in having fucked up. It happens to everyone, all the time.

But what about the people I hurt? The damage is done, and feeling bad won’t change that.  Even more, the people who were affected by your mistakes are well on the way to forgetting about it. They have their own lives and mistakes to attend to.

One more thing. Don’t think about the mistake in terms of your whole life. It’s an isolated event, not a chapter in a lifelong battle against your own personality flaws. If you find yourself dwelling on your whole back-catalogue of missteps, stop. Your life is not a novel. You are not some unchanging character in a Greek tragedy with a character flaw that ultimately leads to your demise. This is just one honest mistake. You subconsciously weighed the emotional and logical pros and cons and made the decision that seemed best. The universe is infinitely complicated and you are only able to model it with seven thoughts at a time, so you made a little error in your judgment. Now you have a valuable experience that you can use to make more informed decisions in the future. That’s all there is to it.

Avoid brooding. You’re in an amazing place. You’re a bouncer who gets to stand between the past and the future and decide what gets through. You’re still in control.

Notes 8/27/13

A Confession…

I am addicted to the Notes app on my iPhone. For years I’ve been jotting down random thoughts all day, every day, intending to come back to them and flesh them out as posts, songs, businesses, novels…something. But any time I tried to go back and use an old idea, it inspired me with ten brand new ideas, and I got so busy writing those down that I never got around to expanding the ancient dustpile of an idea that I set out to work on in the first place.

Today it occurred to me that I’m never going to go back and flesh out my notes. For me the fun of life is in the creation of a thought, the improvisation of a song, a brand new experience you know you’ll never repeat. The truth is that these little notes I take are complete.

So I decided to try this experiment. I am going to start posting some of my day-to-day notes, exactly as they are. It’s no use going back and trying to select my best notes from the past, for the same reason I described above. Instead, following are some of my favorite notes from today. I hope they are valuable to you. They certainly help me, and they’re a lot of fun to write. Every journal I’ve ever kept has looked like this.

I’m very curious if this is something you enjoy reading. What do you think? Do you like these scattered thoughts? Do they fill you with unimaginable rage? Would you prefer if I kept posting them raw, curated them more, posted them as tweets, or just forgot the whole thing and went back to internet silence? Let me know in the comments!

Without further ado…today’s notes!

3 days a week, do nothing unhealthy. Batch all unhealthiness to the other 4 days. So if you’re bad for 4 days straight, tough luck! You have to behave now, for the rest of the week. The count resets every Wednesday night at midnight.


Look for the contradiction in everything. Most people look for the truth. Contradiction is superior because it implies both knowing the truth and knowing how different truths clash with each other. In general, humans are afraid of contradiction. We try to find the right answer to everything, often at the expense of genuine understanding. Perhaps this is why most people just float.


The key to happiness: If you see someone seriously wearing real cowboy boots with a home-cut tank top, basketball shorts, and a baseball cap, compliment him without irony on his wonderful boots. Approach all of life in this way. 


It’s amazing that evolution twisted tiny molecules of DNA into so many shapes and functions through eons of random, almost negligible mutations. Everything you see is is a natural process. We’re so fortunate to be able to experience it.


The fun of life is in observing things. Luckily, that’s also the value humans have to offer the universe: a chance to observe itself.


No one will buy you furniture anymore. You’re on your own. You’re going to have to go out there and find it yourself. Comb through craigslist, sift through the thrift shops, and emerge with your throne. Buy it cheap. Bring your tools, you may have to break it down before you load it in the car. Be brave: This is what adulthood looks like.


You’re never more aware of your breath than when you’re smoking a cigarette. That lovely little grey-tinted, raggedy breath between draws makes it all worthwhile. Just reading that sentence made the smokers want a cigarette. That’s how good it is. There’s a reason the French call orgasm “The Little Death.”


How to manage stay-at-home jobs that are taking up ALL of your time: Stop running from social norms and make yourself work 9-5 (or any other set period of time). No checking work email outside of that time period. Within that time period, respond within 30 minutes to all emails. Must have zero inbox at the end of the day, and zero inbox 30 minutes after the workday starts.


I trust the person who hides his house behind vines and tall, flowering plants, not the person who lays it all bare over an empty green lawn, as if to yell “I have nothing to hide!” I wonder, is this misguided?


Heat begets slowness, cold begets shivers.

Heat begets faithful comfort, cold begets optimistic focus.

Heat begets sweating, cold begets frugality.

Sleep begets sleep, working your ass off begets working your ass off.


Try to see the sunset every evening. Alone is even better. But see it with the love of your life as often as you have one.

How to Define Success

Two years ago, I was given an assignment to write about where I wanted to be in ten years. The assignment was to dream. If everything were to go exactly according to plan, where would I end up?

In my paper, I described a person who didn’t own a home and could fit all of his possessions in a single backpack. No family. A global citizen, I called him. I wrote it as a narrative. He had been in Buenos Aires for six months eating steak and studying Argentinian tango, and now he was ready to move on. He took a taxi to the airport, stared at the departures board, and chose a destination right there and then. Germany, sure. Why not? When the plane was in the air, he opened his laptop and—with a few clicks and short emails delivered through the on-board wifi—delegated tasks to the assistants in India he paid to run his business. After an hour, his work for the week was done and he closed his eyes. A little bit of rest, and then it was on to the next corner of the world.

Since then, I’ve learned that the world doesn’t have corners. In fact, it’s round. Like the homer at a baseball game that all of the children in the stands run and hold out their gloves to catch, as the adults just smile and watch.

Six years ago, I thought I was halfway through my life. All of my heroes stopped at 27. Janis Joplin, Jimi Hendrix, Kurt Cobain, Robert Johnson. All dead. All drug related. I wanted to leave my own music legacy. I would tour the world and then when I was 27 I would follow my heroes with my own glorious burnout. We would be roman candles together, eclipsing stars and blazing trails across the sky until we fizzled out one by one and disappeared into the darkness. I wasn’t going to be a star, twinkling consistent until I disappeared behind the horizon. Not me. I was the schoolyard martyr-in-training, ready to die for that blazing feeling you get in your organs when a firework pops.

Jimi Hendrix died choking on his own vomit. Kurt Cobain splattered himself all over the walls.


Speaking of which, I used to make girls fall in love with me a few times per month. I had a particular talent for finding girls who had given up on romance. Girls with beautiful hearts and strong viewpoints and very deep wounds. Girls with histories. Girls most guys were afraid to touch. Through hours of conversation and careful attention, I made them blossom to where they felt they could finally trust someone with their hearts.

And then I left, usually before I even bothered to touch them myself. No explanation. I just turned cold and moved on. I was an emotional playboy, an internal home wrecker. This is what I meant when I said “speaking of which.” That’s to say, it’s not glamorous. It’s my biggest regret.

Sometimes late at night I pretend to be blackout drunk and I apologize to one of the girls I left. I tell them how honored I am to have spent that time in their company. I tell them that growing up I lived in three houses, and I was never in one place long enough to put up posters, but that doesn’t excuse my actions and I am sorry. Sometimes they say they forgive me. I never feel better.

All of this to say, settling down isn’t my strong suit. In fact, I’ve never even given it a chance. I go weeks at a time without sleeping in the same place for two nights in a row. That’s how it’s always been.

But what if?

This week I turned off the world. I took the car keys out of my pocket and set them on my desk. I cooked all my own meals. I responded to every email. I walked to banks to do research for a project I’m working on and then I came back home. I bought a bookshelf and finally took the books from my suitcase. I read. I drank a lot of tea. I had long conversations late at night with my best friends and said no to everyone else. I wrote thousands of words.

I sent an email to a girl I like and told her I missed her.

All the ways I’ve ever defined success have involved leaving. I wonder, was I really pursuing progress for the sake of where I would end up? I was fast talking, fast learning, fast growing, fast everything. All the time.

Well this week I was domestic, for the first time I can remember. I didn’t feel joyous. I didn’t feel profound. I didn’t feel successful. I felt about as happy as I’ve always felt, which is not that much.

But I did feel calm. And I felt useful. And I felt loved. And my keys are still on my desk.

So now I’m going to say something to you that I never would have dreamed of saying in a thousand years.

I think I want to have kids someday.

Biz Stone, the co-founder of Twitter, gave a talk at my school. Here are my detailed notes on his astounding speech.

Biz StoneNote: I have attempted to be as true as possible to the spirit of his speech as possible, but obviously I could only type so quickly. Without further ado, I present to you Biz Stone’s incredible speech.

The topic of the night: A bunch of stories. These stories are familiar themes with unique perspectives.


  • Failure
  • Opportunity
  • Creativity
  • Technology
  • Empathy
  • A new way to define success


Bob Metcalfe on balance and the secret to happiness

Today, Robert Metcalfe, the inventor of Ethernet, venture capitalist, and all around badass worth over $250 million gave a lecture in the study lounge of my dorm. He was full of wisdom and intriguing stories, but there was one thing he said that stuck with me more than anything else.

“Generally, the people who talk about balance in their lives should not start companies. To succeed you must go all out. You can’t live a balanced life, particularly in the early days of a start-up.”


After the talk, someone asked him if he had any advice for people our age. After a long pause, he looked up and responded, “I can tell you the secret to happiness if you want?”

Everyone laughed. He raised his hand like he was going to testify and shook his head. “I’m completely serious. The secret to happiness is enthusiasm. You have to be enthusiastic about everything you do, or you don’t stand a chance. If you want to do something significant you have to be the best in the world, and if you don’t love it, you won’t put in the work.”

These ideas are directly connected. If you have enthusiasm, you don’t need balance. Were Martin Luther King Jr. or Steve Jobs (Metcalfe’s mentor years ago) concerned with living a balanced life? Would Macklemore have gotten to this superstar status if he wasn’t working 80 hour weeks and travelling constantly?

Balance is for people who are too meek to pick a side, too lazy to determine where they stand, too afraid to put in the work necessary to wrench what they want from life. Find your current passion and get to work.

Reading to procrastinate

Stop reading books about marketing if you don’t have something to market.

Stop reading blogs about management if you don’t have employees.

Stop browsing forums full of advice for pickup artists if you didn’t meet someone new this week.

You’re afraid of failure. It’s okay. We all are. No one wants to do something that flops, so you spend all this time preparing because when you really start you want to be ready. Just one more article, just one more book, just one more case study. Just one more class.

What we forget is the application. If you aren’t applying what you’re reading about, then you aren’t learning. All you know are things that may or not be true. All you know is nothing. When you research without application, your mind becomes the apartment described at the beginning of Fight Club: “A house full of condiments with no food.”

Books are fantastic tools to refine the work you’re already doing. But first you have to be doing work.

It’s okay to make shitty work. That’s called a first draft. Create something and then refine it later. What matters is that you’re doing something. If it flops, at least you’ll have learned one sure way not to do it. That’s probably more than most books have taught you.

So tonight, I want you to pull out your ear buds, unplug the router, and take the bookmarks out of your books—you’ll want to start at the beginning the next time you pick them up. Now press a gun against your temple, take the safety off, look in the mirror, and ask yourself, “What is it that I want to do?” Not what you want to do with your life. What you want to be doing, today. If that gun misfired and your brains splattered over the wall, what would you wish you had used them for this week? This year? You know what it is. You just don’t want to accept it. Forget what you should do. Forget what you tell people you want to do. What would you do if your parents and your grandparents and your teachers and your friends from high school were all dead and couldn’t judge you? What do your heroes do? Not the people you want to have as heroes. The ones you want to meet. What do you do for free? What do you miss sleep for? What movies do you watch over and over? What websites do you frequent? What are all those books about, really?

Once you have your answer, turn the gun on your reflection and fire. Now get to work, and don’t start reading again until you have a first draft.