MICHELLE THALLER: I often get questions from young students, and they say, well, how did you become a success? Or another great question these days is how did you overcome failure? And the funny thing is I found myself really kind of at a loss because the very concepts of success and failure I think are words that never really meant anything. And actually, I strongly suspect they have a lot to do with privilege. That if you can make yourself in the model of a research professor of 100 years ago, that's defined as a success. And if you do something different it's defined as a failure. There's never been any time in my life where, even after having received an award, or having been on a television show, I sat back and said, boy, I really feel like a success. It was always wrapped up in feelings of I should've done something differently, I should've had a different career path. There's never been a time where I felt like a success. And at the same time the idea that you ever really fail at something. There are plenty of times that, I very nearly failed differential equations in calculus, there were things that I was not very good at. But I eventually got them on, say, the third or fourth try. And the problem was just staying around and telling yourself that I really want to learn this, and I'm just not gonna leave until I do. There wasn't any really true failure either. It was always kind of twisted up with things I was proud of, that I was actually working through and trying to learn. So this idea that at some point in your life you're going to stop and feel like a success. Yes, I am successful now. I get very, very nervous when people ask me about that, about how did you become a success. I wanna sit them down and tell them all the things I screwed up, and all the things I did wrong, and all the reasons I'm not a success. And at the same time, when anybody calls me a failure, it's like, I wanna sit you down and explain why what I'm doing is actually getting your money and your funding for the rest of science. I'm not a failure either.

Everything in life is gonna be a flow between those two things. Everything is gonna be a jumble of success and failure. Your personal life, your professional life, the way you feel about yourself. And it's a strange model we give young people. Try to be a success, try to overcome failure. All I can do is just kind of breathe and just realize that at no point in my life am I gonna separate those two.

ARI SHAFFIR: So I was maybe a year or two years into comedy. Went home to this job, came back, and was over-- I haven't thought about this in a while—I was overcome by fright. I couldn't get back on stage. I couldn't do it. I would drive from my apartment in West LA, 30 minutes towards The Comedy Store. Find parking, get out of my car, walk to The Comedy Store. Because you get an employee spot every week, and I was an employee, so you get your three minutes, and it was the highlight of your week. And I would park, go in, turn around, get back into my car, and go home without getting on stage. I couldn't do it. I couldn't do it. I didn't know what to do. So what I did was I intentionally, I mean, it was, that was gonna be the end for me. If I can't go on stage, I can't be a comic, you know? So what I did was, I told myself like do something where it's going to go bad, where you know that ahead of time. Because like, what's the worst that can happen? You know, that kind of thing. So I went to The Comedy Store. I said, I'm not gonna say a word, in my head, I'm like, I'm not gonna say anything for my whole time I'm on stage. And I'm just gonna see what happens. So I went in, I put my tape recorder down, I like press record. And then I was like . And then I just kept looking around, and just three minutes of silence. Like this can't go well. So like, it's not gonna affect me if it doesn't 'cause I'm trying to tank it. But then I could get on stage, I could feel what it's like in front of the crowd. I actually got a couple laughs. Just stuff like, you know, shrugs and stuff, and how ridiculous it was. And then after that I was able to get back on stage again. I was like, that's the worst. I can handle the worst. So now let me go.

KAREN PALMER: So I'm very much inspired by parkour and I am still am a freerunner but I was a really hardcore freerunner training like six, seven days a week for two years at one point like a decade ago, 12 years ago in my life. And I basically didn't realize at the time but me and the people that I trained with were basically completely rewiring our brain. We were learning to understand our own personal triggers for fear and then navigate through there. So say that we were jumping on a ledge that if we fell we might break both our legs. And the distance was quite manageable so what we'd do is we'd start on the ground. Then we'd go up a little bit higher, go up a little big higher. The same distance but as you go higher it's not the distance, it's the consequences that scare you.

So we learned to master our own fear and develop strategies for moving through fear. And often in life when we feel fear we kind of get nervous and we run from it. But really when you feel fear it's something new and probably that's a direction not all the time but often that we should be moving toward to embrace something new. I felt so empowered that it inspired me to change my life like leave my boyfriend, leave my job, change my flatmate, change my business partner, everything. Because I was like well if I can train and I'll jump on this wall and I didn't break my legs what's the worst that can happen if I split out with my boyfriend and I don't think he's the one, right. I basically reprogrammed my brain. And then from that I was able to change my whole life and be sitting here with you today, right.

The kind of key is with parkour is that we kind of say well, you've got to do something three times. And that is kind of like quite a common thing when you're trying to master something. Once is like, you can do it twice and three times now you've mastered it. And that's because neurologically it kind of takes you three times for your neurons to fire in your brain and to create those new pathways. Then it's like sealed.

ETHAN HAWKE: If there was one thing that I've learned that I feel, whatever good fortune is, has put me in the position of realizing this is that without risking looking like an absolute fool, you cannot do anything original, unexpected, anything that comes from your heart. You have to shed that fear of judgment. And that means you may fall on your ass. And one of the wonderful things is that's our job. As a member of the artistic community your job isn't to succeed. Your job is to be one of many people throwing...You're the wind at the door. You're the wave. One wave is going to crash through and it may be you, or it may be somebody else. But there's a lot of waves that are gonna add up to somebody breaking through. I mean, do you think people really...Look, when Linklater and I first were going around trying to pitch the idea of Boyhood. I got an idea, right? We're going to make a little short film about a little boy for 12 years. We're going to cut it together, it'll be one movie. It'll be all about childhood, it'll be amazing. So wait, it's coming out in 13 years? And wait, does the little boy sign a contract? You can't sign a contract for more than seven years. Yeah, but if the boy is having a good time...Yeah, so I put my money in now, and if the boy is having a good time, I get it back in 13 years? Yeah. Nice. What else do you have? But luckily the guy went with me and yeah, we could have fallen on our ass, but you have to try. You have to try.

STEVE CASE: Great breakthroughs in society usually have required multiple tries, multiple experiments, multiple pivots. And that's the whole idea of getting in there, getting some experience, and then taking a step back and figuring out how you move forward. The most classic case of this was the whole idea that John F. Kennedy started about getting somebody into space, landing somebody on the moon. When he said that, he called for the country to rally around that, it almost was impossible for people to imagine that happening. The technology just wasn't there, but people tried things. Many times failed. This they thought would work, it didn't work. They kept adjusting, kept at it. And eventually they were successful in landing somebody on the moon and bringing them back home safely. So that's a perfect example of many different experiments. People see this in science, they know that in order to have a breakthrough in science, you have to try a lot of things. Most things will fail, but that doesn't mean you're a failure, that just means that idea failed. And what can you learn from that idea and then move forward.

TIM FERRISS: In Silicon Valley, there's the fail fast, fail forward, the fetishizing of failure. And it's become very trendy. I think it's extremely misleading and misinterpreted and misapplied in many cases. So whether you ask, say Peter Thiel who views failure as always being a tragedy. There is no exception and it is not some aesthetic imperative or learning imperative necessarily. Or you talk to, say, Mark Engstrom, for instance, who I interviewed for Tim Ferriss Show, but also for Tools of Titans. And he says, "When I was getting started," I'm paraphrasing here, but well, "When I was getting started, we didn't have a fancy word for it. We just called it a fuck-up. We didn't call it a pivot." I think that it would be better to say iterate fast and iterate forward. I certainly feel like doing your homework coming out, and maybe the Silicon Valley ethos should start looking into the military more to say, I think it's David Hackworth. I think I'm getting that right. Who said, "If you find yourself in a fair fight, you didn't prepare properly." Or something along those lines, I mean it is entirely plausible and possible to come out and just smash your competition from second one of round one. And I think that even if you do end up failing and then correcting course, that's a good aspiration to have. Not to come out really shoddy and handicapped from the get go expecting to pivot 27 times. Then if you look at my portfolio, for instance I have about 70 companies I've invested in, I was a pre-seed advisor to Uber and Uber's business model hasn't really changed. It's been the same for a very long time. If you look at Derek Sivers, the founder of CD Baby. He came up with the business model in about five minutes of going to a used record store and asking them how they did it. And it remained the same effectively for 10 years, 15 years until he sold it for whatever it was, $24 million. So you don't have to fail. It's not a prerequisite for having a successful company or a successful life. You just have to learn. So I think learning and iterating are two words that are going to be more valuable than failure. But when failure does slap you in the face when fortune serves you up a tidal wave of some type or quicksand being able to adapt to that and not emotionally overreact I think is certainly important but you shouldn't strive for failure.

ALISA COHN: The best way to debrief any project, any bad thing that happened, any problem, is just to go down the tiers of why. And so you start with, okay, so let's assume that the project that you were working on is late. Let's assume it's a product release and that it is now definitely not gonna make its deadline, and it's probably three or six months late. First of all, it's important just to create an environment where people can talk freely and not feel blamed, because we're just debriefing to understand what happened. So it's about understanding the structure of it, not looking to finger point. But the first question is why? So why was the release late? Well, engineering for example, didn't deliver the code on time. Why didn't engineering deliver the code on time? Because they weren't given the specs early enough. Why weren't they given the specs early enough? Because product didn't get to them early enough. Why didn't product get to them early enough? Because product didn't understand from marketing the requirements early enough. So if you keep going down those and you understand why did marketing not get them early enough, it's because they didn't have a good plan to get the customer data they needed to. Then you can take a look at what went wrong here. Is it about, we need to tighten up our process? Which is very often true, especially with startups. Is it that we need to have a better timeframe for deliverables? Which is often very true when you're working on complicated multi-domain projects. Or, did we just forecast incorrectly? Did we not take into account all the multiple steps that leads to the product release? And that's often very true as well. And maybe, why didn't we take into account the multiple steps? Because there wasn't one person in charge. Great. So going forward, we know that we need to all take into account the multiple steps, and declare one person the owner of the project overall. And let's try those two interventions, those two changes. And that's gonna help us be more, have more excellence in operations.

CASE: Sometimes you do have to call it quits. So sometimes things are just not working. But my own experience is sometimes just when you think that, finally something breaks through, and the sky opens up, and there's new possibilities. We came very close to not making it with AOL. There was many times where it didn't quite work. Where you thought something would work, it didn't. We have to lay people off. We're about to run out of money. We had a partnership that fell apart. There were some near death experiences on that road. I used to joke that AOL was a 10 year in the making overnight success. By the time it finally got successful, everybody said, you came out of nowhere. No we didn't, we were at it for a decade. And thankfully we didn't give up, we didn't quit, we stuck with it. So sometimes you have to just say, it's not working, you have to walk away. But my experience is if you really believed in that idea early on, you really were passionate about that idea, you still think it could get traction. For some reason, it just hasn't broken through. Take a fresh look at what partnerships you can establish that help accelerate the growth. What new policies perhaps can be put in place to accelerate the new growth. Don't give up on it. Now, there's a great Nelson Mandela quote: "It always seems impossible until it happens."