The Tim Ferriss Show - #292: Lessons and Warnings from Successful Risk Takers

Episode Date: January 18, 2018

This is a special episode of the podcast, which features three guests: author Soman Chainani (@SomanChainani), author Susan Cain (@susancain), and East Rock Capital co-founder and investor Graham Duncan.All three are featured in my latest book, Tribe of Mentors, and all three share something in common: they're experts at mitigating risk. I don't view them as a throw-caution-to-the-wind; nonetheless, they've been good at capping downsides and making various career decisions that have paid off in large ways.I hope you enjoy this episode with these three brilliant guests!This podcast is brought to you by Ascent Protein, the only US-based company that offers native proteins -- both whey and micellar casein -- directly to the consumer for improved muscle health and performance. Because the product is sourced from Ascent's parent company, Leprino Foods -- the largest producer of mozzarella cheese in the world -- it's entirely free of artificial ingredients and completely bypasses the bleaching process common to most other whey products on the market.If you want cleaner, more pure, less processed protein -- which I certainly do -- go to ascentprotein.com/tim for 20 percent off your entire order! I'm a big fan of all of their flavors -- the chocolate, vanilla, and even their newest option, cappuccino. Enjoy!This podcast is also brought to you by 99Designs, the world's largest marketplace of graphic designers. I have used them for years to create some amazing designs. When your business needs a logo, website design, business card, or anything you can imagine, check out 99Designs.I used them to rapid prototype the cover for The Tao of Seneca, and I've also had them help with display advertising and illustrations. If you want a more personalized approach, I recommend their 1-on-1 service. You get original designs from designers around the world. The best part? You provide your feedback, and then you end up with a product that you're happy with or your money back. Click this link and get a free $99 upgrade. Give it a test run...***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Interested in sponsoring the podcast? Please fill out the form at tim.blog/sponsor.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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This episode is brought to you by Five Bullet Friday, my very own email newsletter. It's become Check it out. includes apps, books, documentaries, supplements, gadgets, new self-experiments, hacks, tricks, and all sorts of weird stuff that I dig up from around the world. You guys, podcast listeners and book readers, have asked me for something short and action-packed for a very long time. Because after all, the podcast, the books, they can be quite long. And that's why I created Five Bullet Friday. It's become one of my favorite things I do every week. It's free. It's always going to be free. And you can learn more at Tim.blog forward slash Friday. That's Tim.blog forward slash Friday. I get asked a lot how I meet guests for the podcast, some of the most amazing people I've ever interacted with. And little known fact, I've met probably 25% of them because they first

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that you'd dig it a lot and you can, of course, easily subscribe any time. So easy peasy. Again, that's tim.blog forward slash Friday. And thanks for checking it out. If the spirit moves you. Hello, ladies and gentlemen, boys and girls, this is Tim Ferriss and welcome to another episode of The Tim Ferriss Show where each episode it is my job to tease out the habits, routines, belief systems, decision-making frameworks, whatever it might be, backstories, failures and what they've learned from them that you can borrow from performers and apply in your own lives in some fashion. In this episode, we're going to feature three guests, Soman Chanani, Susan Cain, and Graham Duncan. And I won't get into their bios right now. Soman Chanani was introduced to me by Brian Koppelman, some of you may know,

as the co-creator of the hit show Billions, as well as a filmmaker, writer, director known for flicks such as Rounders, The Illusionist, and the list goes on and on. Susan Cain, speaking myself as someone who considers himself an introvert who can, for short periods, pretend to be an extrovert. What she writes about is very, very applicable to my own life. And Graham Duncan, very understated person who tends to stay out of the public eye, out of the limelight. And you may notice, for those of you who spotted the names, all three of them are featured in my latest book, Tribe of Mentors, that Graham Duncan has no social media profiles in the book. And that tells you a

lot about Graham. All three of them, I should note, share something in common. And that is that I would view all three as people who are very, very expert at mitigating risk. So I don't view them as a throw caution to the wind, risk it all bunch whatsoever. Nonetheless, they've been very good at capping the downside and making various career decisions and bets that have paid off very, very, very, very large. So I hope you enjoy this as much as I did. And I will let these three brilliant guests take it from here. Our guest today is Soman Chainani on Twitter at Soman Chainani, S-O-M-A-N-C-H-A-I-N-A-N-I on Instagram at Soman C, or you can find more about him, Soman Chainani dot net. Soman is a detailed planner, filmmaker, and New York Times bestselling author. His debut fiction series, The School for Good and Evil, has sold more than a million copies,

has been translated into more than 20 languages across six continents, and will soon be a film from Universal Pictures. A graduate of Harvard University and Columbia University's MFA film program, So-Man began his career as a screenwriter and director, with his films playing at more than 150 film festivals around the world. He was recently named to the Out 100 and has received the $100,000 Shasha Grant and Sun Valley Writers Fellowship, both for debut writers. So the right book can slip right inside of you and somehow wake up the part of you that's asleep. It can actually put words to the thoughts

that your soul can't quite get a hold of without at least a little help. And there's so many books that have done this for me, but there's three in particular that I've read over and over and over. The first is The War of Art by Steven Pressfield, which is this slim, tiny little book about the creative process.

It's almost like a Tao Te Ching for artists, that every time you read, lets you go deeper and deeper into this idea of overcoming the innate resistance that faces anybody who wants to make a change in their life, especially a creative one. And every time I read it, it lights this crazy bonfire inside of me that reminds me just how far I have to go in order to trust the creative voices inside of me instead of the ego voices. Because that's the real crisis with all creative work, is that it requires us to trust the silent voices, the ones that we actually don't hear as loud as the positive and negative ones that are always judging the work that we do. And it's easy to mix all

these voices up and end up quietly abandoning your own ambition often before you even start your project. These ego voices are also why I became a pharmaceutical consultant at 21 years old, hawking Viagra instead of writing fantasy books and movies like I do now. Because at the time, a pharmaceutical consultant felt like a safe job, the kind of normal job that you tell your parents about and they tell their friends about and makes you feel like you're doing something right with your life. And so these ego voices are also why I'm afraid to date Ivy Leaguers, I guess, even though I reluctantly have to admit that I am one. Because when you go to an Ivy League school, you're tagged as a success before you even accomplish anything, before you even know who you

are. And so it stokes this very fragile sense of self and it makes you play it completely safe. And ultimately, to make any real progress in my own life, I had to decondition myself from my own education and really believe that I had nothing to lose. So yes, Pressfield's War of Art, that's where I would say the yellow brick road starts. For a second book, I choose something unusual, which is A Little Life by Hanya Yanagihara, which is a whopper of a novel that tracks the friendship of four male friends in New York City over the course of almost 40 years. You honestly won't find a book more polarizing or divisive, but to me, it's the greatest

work of fiction I've ever read, primarily because it hits a nerve that I've struggled with my whole life, which is that all of us have baggage and wounds and pain that have shaped the way we see the world, but we so often hide it or compartmentalize it, and because of that we close off parts of ourselves and make our lives a lot smaller. A Little Life reminds us that the pain we feel is shared and it's a common human bond. We shouldn't be ashamed of it. And that if we talk about it and shine a light on it, it's the first step to becoming a whole person instead of a fragmented one. I honestly can't imagine a more ambitious or healing or moving book. But what's

also funny is that a lot of people hate A Little Life and consider it the worst book ever written. My brother despises it, and he says, quote, it's trash, basically the literary equivalent of rubbernecking at a car accident. So take that for what you will. Tim, if any of your listeners end up reading A Little Life, I'd be curious to hear which camp they end up in. And then I was thinking for the third book, given my profession, it made sense to think a little younger. Because I honestly think the greatest exercise you can do when you're stuck or in a rut in your life is to remember what your favorite children's book was. A book that you read over and over and over again and never got tired

of. Because somewhere in that book is a clue to not only what makes you tick, but also to your life's purpose. My book was Peter Pan, which featured a title character who was at once charming and also a complete narcissistic pathological demon. And I think it was that ambiguous space between good and evil that I sparked to as a kid. And I'm now exploring for a living as an adult. What purchase of $100 or less has most positively impacted your life in the last six months or in recent memory? Ooh, this is easy. It's called Mother Dirt. It clears your skin, and it costs $49. My skin was a hot mess for most of my adolescence and into my 20s. And when skin problems fall you into adulthood,

it's so frustrating because it becomes completely demoralizing and it psychs you out and it wreaks havoc on your self-esteem. And in my case, I tried to fix it with willpower, which meant that I tried every single product on earth. I tried antibiotics, which kill your stomach. I tried harsh cleansers, which dry out your skin and really make everything so much worse. And then I was trying every three-step cleansing program this side of Sephora, which just left my skin even more inflamed and wrung out. But then four years ago, I discovered mother dirt in a New York Times profile. Back then, I think it was known as AO plus biome. And their theory was super simple. It was that skin naturally needs

AOB, which is short for ammonia oxidizing bacteria, in order to stay healthy and clear. But soaps, creams, and all the things we use to help our skin end up killing all that natural bacteria. So if you stop using those products and restore that bacteria naturally, then all of a sudden your skin goes back to its normal healthy state. So my brain instantly connected with this. I was like, yes, this makes sense. I want to try this. So I wrote them begging them to become one of their beta testers. And luckily they agreed. And Mother Dirt came in a little spray bottle, which I kept in my fridge. And within a week of using it, my skin was really

completely clear, and I've been using it for four years every single day. The trick to making it work, though, is not to use other products that'll kill the bacteria while you're using Mother Dirt. Mother Dirt literally becomes your routine. So I threw out all my fancy zit zapping, pore unclogging, oil unchiming, microderming, we promise this will make you look like Natalie Portman, creams and toners and cleansers, all of it. And it was really the best day ever. And all I do now is spray my face twice a day with Mother Dirt. I don't use anything else. It's that easy. Their website is motherdirt.com. And I have tons of experience with this product. So your listeners should feel free to shoot me questions if they have any of them, if they want to try it or if they're using it. How has a failure or apparent failure set you up for later success? Do you have any favorite failure of yours? This story hurts to tell. I

don't know if I've ever told it. The biggest failure I ever had was with my thesis film at Columbia's Graduate Film School, a movie I'd poured all my savings into at that point, about $25,000, and worked on for eight months. And a day before my final showing to the faculty, I suddenly got a really bad case of cold feet. And there was a reason for this, which goes back to what I said earlier about Ivy Leaguers and fragile egos. Columbia Film School had this diabolical little system, which I don't even know if they still have today. But after the first year, the faculty all got together and gave out this one big cash prize, I think it was $16,000, to whoever they thought was the most promising director. I ended up getting that prize, which ended up being a lot more of a curse than anything,

since it directly led to the failure that happened next. So with my thesis film, I wanted to prove so badly that I deserve that prize, that I was the most promising director, that they put their faith in the right student. So the night before my jury showing, you know, instead of being content with all the work I had put into that film, I completely panicked and decided I should show it to one of the professors on the jury, hoping that he'd reassure me. He didn't. He thought it was slow and, quote, feckless. That word still stings anytime I hear it or read it, and recommended I slash the whole movie to pieces and make it half the length. Instead of looking for a second opinion

or balancing his feedback against my own thoughts of my work, I panicked like I was a headless rooster. This professor was obviously on the jury and I wanted to stay the faculty's blessed son, and so I trusted external validation at this point in my life more than my own creative compass. So like a lemming, I followed his advice. I spent the whole night undoing eight months of work and recutting the film. And the next day I presented it, this hacked up Frankenstein to the faculty who absolutely demolished it. They literally thought it was the worst movie in our class, probably one of the worst movies they'd seen, you know, come into the thesis presentations. All credibility I'd earned over the past three years went up in smoke. I wasn't invited to participate in the Public Film

School Festival. Lots of gossip about how I never should have gotten that scholarship floated around, how I had no talent, how I'd let the prize get to my head. And of course it did, just not in the way that they all thought. A few weeks later, I ran into one of those disappointed faculty members, one who'd been a huge supporter of my work before this and now could barely look at me. I told him the story of the last minute recutting I'd done the night before my presentation, and he asked me if he could see the original version. So I showed it to him and I just remember the way his eyes kind of lit up like stars and he said, ah, there you are. Now I see you. Incidentally, that short film in its original version went on to great success and it started

my whole career. But here's the lesson that I, you know, remind myself of constantly, and I hope you can take away from it, which is that don't let someone knock you off your course after you've put in all the work. You have to trust the work. You have to always trust the work. If you could have a gigantic billboard anywhere with anything on it, what would it say and why? If I was in Hollywood, the billboard would say, they're lying. And I actually have to remind this to myself all the time. Every time I'm on a call with a Hollywood producer or studio executive, I actually pull up a screensaver with those two words, they're lying in all caps. And I watch it sort of spread across the screen during the call

over and over. And it makes the whole experience a lot more productive and less frustrating. This reminds me of my first experience in Hollywood. I was coming out of film school. I'd written a script that a lot of producers and studios were interested in. And at my first ever studio meeting, the exec sweeps into the room, crows it's the best script that he's ever read. And he's like, kid, we are making this movie, and he slams his fist on the table. After that meeting, I never heard from him

again. And yeah, obviously, he didn't make the movie. But I think it's a depressing billboard to focus on Hollywood's lies, so let's pick another one. If I'm anywhere but LA, the billboard would say, if you can conceive of it, it's probably wrong. And years of meditation taught me that most of the ideas and opinions and rules and fixed systems I have in my mind, those aren't the real truth. They're the residues of past experience that I haven't found a way to let go of. And to be open to life, to be truly ourselves, it's our job to be aware, only aware, not to clutter that precious awareness with judgments. So I need meditation as my primary weapon to survive life, to let me study my own brain like a detective, looking for thoughts or thought patterns that I can let go of.

Because the secret to happiness, I've learned, isn't really happiness at all, but cultivating silence inside of me, this big, blank, beautiful space. And the only way I know how to make more blank space is through meditation. So 20 minutes a day, every day, wherever I am, often I use the Headspace app because it logs your progress. So it gives you a little bit of an incentive to keep a streak going. But all you need is a comfortable chair and silence and meditation becomes the portal to the rest of my day. What is one of the best or most worthwhile investments you've ever made? Oh, it's definitely flying trapeze lessons. Those are like shock therapy for the

soul. Because as soon as you get on the platform for your first class, it's 50 feet high. And so you're instantly making all these cerebral calculations. You're like, I'm going to jump this way. And then I'm going to do this. And then my legs are going to go over the bar here. And I'm going to drop into the net there. And it's all complete and utter BS. Because once you jump off the platform, you realize in an instant that you have two choices. Either you trust your body, or you die. And for someone who makes a living with my head, I need that kind of primal therapy to reintegrate with my body in a very sort of forceful, violent way. And just one classmate realized that underneath my mind's chatter,

my body actually has everything under control. If I'm willing to just, you know, take the plunge and fly. This reminds me of a related story, which is that I'm a compulsive crossfitter. And at first, my favorite skill when I started the classes was box jumps. It felt so controllable that if you just jump on a box of a certain height and you clear it, you get to build the box higher and try again. It was linear, it was Pavlovian, and it rewards a control freak like me in the clearest possible way. But at some point I hit a plateau and I couldn't jump any higher. I got frustrated. I tried to will myself higher. I was watching YouTube videos all day trying to

find out like what I was doing wrong. And it just led to me forcing it again and again and again and compromising my form and wiping out a lot. And, you know, no matter how much I grit my teeth and did it again and again, I couldn't get past my max of 42 inches. So I finally said, that's my max. I told my trainer, Dave, I said, 42 inches, that's it. That's my complete max. And he disagreed. He's like, you've gotten to this height by jumping. Anyone can jump. You can control a jump. But the only way you're going to get any higher is by flying. And you can't think your way through flight. So I had to relearn box jumping to get past my self-imposed max, my cerebral max, and find my real maximum. And this required the same trust in my body as a trapeze did. Jump, commit, let the body do the work. And if there's one thing you can take from this, it's that you can find something in your own life that forces you to

have this experience. Jump, commit, let the body do the work. Whether it's trapeze lessons or an improv class or just freestyle dancing in your room to Rihanna, let your body show you its natural intelligence. Give it the chance to show you. It's going to be the most intimate experience you ever have with yourself. What is an unusual habit or an absurd thing that you love? I feel like this is a guilty pleasures question, and I have so many of those. Everything from Celine Dion to peanut butter slathered popcorn to the movie Showgirls to that horrible TV show ALF. But here's one I guess that's more important to me, which is, and it's not something I confess regularly, but every night

before I go to bed, I pull out old issues of Archie comics and read them. It's not a new habit. I used to read Archie as a kid before I went to bed back then also. And it's because Riverdale's in the comic always seems so crisp and bright and welcoming. Riverdale was a complete opposite of the kind of school I went to, which always felt so dark and morose and always made me feel scared somehow before having to go there on Monday mornings. And so just reading the Archie comics gave me this soothing, warm feeling before I drifted off to sleep that I still get to this very day when I read them. But maybe more importantly, closing the day by reading the same thing I did when I was younger gives my life this sense of perfect order somehow.

Maybe there's a deeper lesson in this also. I know I'm technically a writer of young adult literature, but I never think of my audience that way, or I never think of myself as a writer for kids. Because I think the things we love when we're young are still the things we love when we're older. We just forget or we give up or we, quote, grow up. And that's why the old fairy tales always held so much power for me. Because they worked for everyone, young or old. It didn't matter who you were. Just like Archie works for me, young or old.

And so maybe we all grow up in body one day. But I'm not sure our soul ever does. And that's why the best stories somehow can touch us all and transcend things like age or nationality or culture or anything like that. That's why the best stories are universal. In the last five years, what new belief, behavior, or habit has most improved your life? I know I should offer something deeply profound here, but honestly, the thing that's most improved my life in the last year is unfollowing hot people on Instagram. There's this amazing short story by Ted Chiang that started all this

called Liking What You See that did a real number on me. The story asserts that beauty has become this kind of alien modern day super drug that with filtered and face tuned social media and retouched models on ads and porn so easily accessible, we've completely overloaded the senses and overstimulated ourselves so that our natural instincts can no longer recognize or react to real beauty anymore. And that's making us confused and miserable, both in how we judge ourselves and also how we judge others. And that crystal clear warning that beauty is literally ruining our lives like the worst drug woke me up. Because if we're not careful, and this is where I fell into this trap and was completely guilty of it, our social media feeds become filled with people

we follow only because they're beautiful or because we're envious of their lives. And without really realizing it, your feed turns into this torture device, an assault of beauty and perfection designed to make you feel inadequate. And so opening up Instagram doesn't inspire you anymore. It just makes you start to hate live your own life since you can't possibly measure up to the gods and goddesses of all these perfectly filtered pictures. And it makes you intolerant of other people's real imperfections, and then it makes you start to despise the weight of real people and real life, and invest in shallow, flimsy, kind of 2D mirrors of it. It makes you constantly judge your own life against others. It makes you fragment your own consciousness because you're living outside of your own life in order to get the perfect picture of it. It's completely and utterly deadly. And so I would say you have to use social media to make yourself better, to make yourself feel

better, not to punish yourself. And that honestly has been the most valuable change in my life in the last couple of years. What advice would you give to a smart, driven college student about to enter the real world? Let's start with the advice that I'd give, which is make sure you have something every day that you're looking forward to. Hopefully it's your job, but if it's not, which is a completely universal and understandable condition, maybe it's a basketball game after work or a voice lesson or your writing group or an open mic night. Maybe it's a basketball game after work or a voice lesson or your writing group or an open mic night. Maybe it's a date. Have something every day that lights you up because it'll keep your soul hungry to create more of these moments instead of getting dragged down into kind of

the rut of having, you know, a job that you're not excited about. And I'll also remind you what really fulfills you in life. When I was a pharmaceutical consultant and I was completely miserable, I used to come home from work and work on my novel that would eventually become The School for Good and Evil. I never intended to publish it. I never intended anyone to read it. I just did it to offset the misery of a job that I hated. And over time, I loved writing the book so much

that I used to leave early sometimes in order to work on it. And slowly, the novel started to take over my work life, too. I found myself secretly working on it in the mornings, during meetings, in the corner during office, during lunch. And eventually, I got fired because they figured out I wasn't doing any of the real work, and I was actually working on my book. And the truth was I wasn't upset, because I had discovered what had made me happy at that point, which was telling stories. And nothing was going to put that genie back in the bottle. As for advice I'd ignore, a little part of me dies

every time someone tells me that they've taken a job as a stepping stone to something else, when they clearly have no interest in that job whatsoever. And I think it's because the truth is you only have one life to live. Time is super valuable. It's the one currency that we're all fighting to get more of. And so if you're using the idea of stepping stones and jobs that you're not really interested in to get somewhere else, you're probably relying on somebody else's path or definitions of success that was created in the past.

And I think it's more important to live in your own present and try to make your own path. It's going to end up being more fulfilling for your own life. What are bad recommendations that you hear in your profession or area of expertise? I think too often aspiring artists put this pressure on themselves to make their creative work their only source of income. That they can't be an artist unless they're a full-time artist somehow. And in my experience, it's just a road to complete and utter misery. Because if art is your only source of income, then there's unrelenting pressure on that art. And mercenary pressure isn't just the enemy of the creative elves inside you trying to get the work done. But mercenary pressure also often leads to really bad and rushed work. So having another stream of income drains the pressure on your creative

engine. If nothing comes of your art or it flops miserably, whatever, you still have an ironclad plan to support yourself. And so your creative soul feels a lot lighter. It feels free to do its best work. And I'm still a personal practitioner of this, even though I could easily be a full-time writer, because after four books and a movie deal, I want a separate size stream of income in order to be able to write without feeling like it's a matter of life and death. So I tutor kids on the side. I help them with their college applications. And I've been doing that for the last 10 years and really no plans to stop because it makes the books better in the end if I don't feel like the books are my only source of livelihood. In the last five years, what have you become better at saying no to?

I'm convinced that the reason Hollywood movies are often so terrible is because everyone is so busy hedging their bets that they're working on a thousand projects at once. They don't want to commit to anything for fear that it's going to fail. No one is giving anything their full focus. So when I worked on The School for Good and Evil, I decided to take the opposite track. I decided to commit completely. And the series has taught me to be patient. Because when I'm writing a new book, that's all I work on. And I say that's all I work on, and I say no to all other creative projects, no matter how lucrative. Do I miss opportunities? Absolutely. But it means that when the books hit the shelves,

I know that I've left everything on the page, and they're the absolute best I could have done, which then gives the series the greatest chance to survive through time. It's easier to say no, though, when professionally I know what my driving need is. Because if your driving need is to build income and provide for your family, then you'll say no to anything that doesn't further that goal. But if your driving need is to have your own business, for example, then you need to be a bit more promiscuous in trying out ideas until the right one hits. In my case, my driving need is always unequivocal,

which is I want to make something that lasts. And that means committing to my current work like a marriage and believing that if I give these six books in the series everything I have, then better opportunities will eventually rise to replace the ones that I passed up. When you feel overwhelmed or unfocused, what do you do? So feeling overwhelmed usually means one of two things. Either my blood's trapped in my head and I need to get out there and exercise and move the blood around and give myself space to breathe. Or more likely, my to-do list has become completely overpacked and my brain knows there's no way I can reasonably get done everything I've set out to do.

And so that's when the solution is taking out the calendar and start canceling things, moving things around, seeing what I can take off my plate and then I can feel the paralysis evaporate once I've hit that threshold of knowing that I can reasonably accomplish whatever I want to do now. Feeling unfocused is a little different, because it usually means I haven't quite locked into whatever I'm working on, that a part of me still thinks I can pull the ripcord and bail and is afraid to commit. It usually happens in the first three months of writing a new book, because that lack of focus is usually just fear. Fear that the new book is terrible, fear that it's going to fail miserably and sink

my career. Early on, I used to give in to that fear. And four books later now, I know that I just have to hold on tight, grit my teeth, and blow right through it like a ghost. Our guest today is Susan Cain, C-A-I-N, on Twitter, at Susan Cain, Facebook, author Susan Cain. Quietrev.com is her website. Susan is the co-founder of Quiet Revolution and the author of the bestsellers Quiet Power, subtitle, The Secret Strengths of Introverted Kids, and Quiet, subtitle, The Power of Introverts in a World That Can't Stop Talking, which has been translated into 40 languages and has been on the New York Times bestseller list for more than four years straight. Quiet was named the best book of the year by Fast Company Magazine, which also named Susan one of its most creative people in business. Susan is the co-founder of

the Quiet Schools Network and the Quiet Leadership Institute, and her writing has appeared in the New York Times, The Atlantic, The Wall Street Journal, and other publications. Her TED Talk has been viewed more than 17 million times, probably more than 20 million at this point, and was named by Bill Gates as one of his all-time favorite talks. How has a failure or apparent failure set you up for later success? Do you have any favorite failure of yours? So a very long time ago, I used to be a corporate lawyer and I was a very ambivalent corporate lawyer and anyone could have told you that I was in the wrong profession, but still I had dedicated tons of time to it. You know, three years of law school, one year of clerking for a federal judge, six and a half years at a

Wall Street law firm. And I had a lot of very deep relationships with fellow attorneys. But the day came when I was very well along on partnership track that the senior partner in my firm came to my office and sat down and told me that I would not be put up for partner on schedule. And to this day, I really don't know whether he meant that I would never be put up for partner or just delayed for a long time but all I know is that I burst into tears right in front of him and then asked for a leave of absence and I left work that day and I remember bicycling around and around Central Park in New York City having no idea what I was going to do next. I thought I'd probably travel. And I had all kinds of plans to go to India and so on.

But instead, and this all happened in such a kind of sudden and cinematic way that it will defy belief. But what happened is I remembered that I had always wanted to be a writer, which seems strange. You would think I had always had that in the back of my mind. But my writing dreams were something I forgot about, had forgotten about for a very long time. But I started writing that very night. And then the next day I signed up for a class at NYU in creative nonfiction writing. And the next week I went to the very first session of that class. And it really was like a kind of epiphany moment.

I felt like I was finally home. I had no expectation of ever making a living through writing, because you always hear about how difficult that is. But it was just clear to me that from then on, I was going to put writing at my center. And so I decided to just look for freelance work that would give me lots of free time to feed my hobby. Now, if I had succeeded at making partner on schedule, I might still be there today, you know, kind of miserably negotiating corporate transactions 16 hours a day. It's not that I had never thought about what else I might want to do other than law,

but there's something about being inside a very intense 16 hour a day hermetic culture, like a law practice, that makes it really difficult to figure out what else you might want to do. What is one of the best or most worthwhile investments you've ever made? Best investment I ever made was the seven years of time that it took me to write Quiet. I really didn't care how long it took. And though I very much wanted the book to succeed, I felt good about that investment of time, regardless of the outcome, because I really didn't know what was going to happen. But I felt so certain that writing in general and that writing that book in particular was the right thing to do. So what happened is, well, first of all,

I had two kids along the way. So of course that slowed me down. But also I handed in a first draft after the first two years. And my editor basically said, this is very crappy. And she said, take all the time you need and start from scratch and go home and get it right. And you might think that that was a moment of grand discouragement, but it was actually exactly the opposite. I remember leaving her office elated because I agreed with her and I knew I needed a lot of time to get it right. And I was thrilled that the publisher was giving it to me. You know, I had never published a word before Quiet and I felt like I was learning how to write a book from scratch. And most publishing houses rush books to market a long time before they're really fully done, you know, just because of economic

exigencies. And I feel like if she had done that, there would be no quiet revolution. What is an unusual habit or an absurd thing that you love? I really love sad, minor key music. And the funny thing is, I find that kind of music very elevating and transcendent, and not actually sad at all. And I think it's because this kind of music is really about the fragility and the preciousness of life and love. So if you're curious about some examples, for me, Leonard Cohen is my patron saint. You could try listening to Dance Me to the End of Love or to Famous Blue Raincoat or pretty much to anything that he's ever written.

If you're not familiar with his work, I'm sure you know his song Hallelujah that has been made into a cover a gazillion times, but that really is only the tip of Leonard Iceberg. I also love this song called Hinach Yaffa by an amazing guy named Idan Reichel. It's a really gorgeous song of a man longing for his beloved, and it's really about longing in general, whether longing for God or for heaven or whatever. My favorite word in any language is the word sodaje, which is the Portuguese word that's at the heart of Brazilian and Portuguese

culture and music. And it basically means a kind of sweet longing for a beloved thing or person that will likely never return to you. And I know that sounds so desperately sad, but again, it's so hard to articulate it, but there's something so incredibly beautiful and transcendent in that very idea. And if you want to hear the music expressing that idea, you could try a band called Madre Deus or the singer Cesaria. I'm not sure I'm pronouncing her name correctly, but Cesaria Evora, something like that. And by the way, my next book or my whole kind of next work chapter of my life is all about this topic of how loss and longing are such an essential part of love and art and growth in general. What advice would you give to a smart driven college student about to enter the real world? Smart driven college student. You're going to

hear so many stories of people who risked everything in order to achieve this goal or that goal, especially when it comes to creative goals. But I don't believe that your best creative work is done when you're stressed out because you're like on the edge of bankruptcy or some other personal disaster. It's really just the opposite. So you should be setting up your life in a way that's as comfortable and happy as possible. And that often means setting it up in a way that doesn't appear very creative on the outside because you're tapping into kind of more conservative structures. But what you're really doing is freeing yourself up to accommodate your creative work. So I often ask myself whether all those years of

Wall Street law were a waste, given that what I really was meant, I think, to be doing the whole time was to explore human psychology and do what I love to do now, writing about what it's like to be alive. It's really how I think of my work. But the answer is that no, it was totally not a waste for so many reasons. I mean, first of all, because I learned so much about the so-called real world that would have otherwise been a mystery to me. And second, because a front row seat at a Wall Street negotiation is as good a place as any to study the ridiculousness of being human. But most of all, maybe, is because those years that I spent practicing law gave me a financial cushion when I was ready to use it to try out a creative life. It wasn't a huge cushion. I had not managed

to save that much, but it did make a huge difference. So even once I started my writing life, I spent tons of time setting up this little freelance business on the side where I taught people negotiation skills. And it was something that I felt I could use as long as I needed to, to support myself when my, my real center always was writing. And I, I like the, the thing I was trying to do the whole time was take the pressure off the writing so that the writing could always be a source of joy and satisfaction. So I told myself that my goal was to get something published by the time I was 75 years old. And that was it. So I met my goal a lot earlier than that. Okay, so I am not saying, by the way,

that the smart, driven college student who wants to have a creative life should spend 10 years in corporate finance first. Very much not saying that. I'm really making a more basic point that you should just be planning how you're going to make ends meet and have a way to do that. And that way, the time that you do spend on your creative projects, and it could be 30 minutes a day, it could be 10 hours a day, but you want those moments to be about focus and flow and occasional glimpses of joy, and you do not want them to be associated with financial stress. When you feel overwhelmed or unfocused, what do you do? I love espresso and I would happily consume it all day long. But I'm really afraid of habituating to it and losing its magic powers. So I only allow myself to have one latte a day and I save it for

when I'm doing my most creative work of the day because it really does jumpstart my mind in this almost magical it has a kind of magical power and also by now I associate latte in a kind of Pavlovian way with writing which then gets associated in a Pavlovian way with the pleasure of coffee. So it's all a really good feedback loop. My guest today is Graham Duncan. You can find out more about him at EastRockCap, C-A-P dot com. Graham is the co-founder of EastRock Capital,

an investment firm that manages $2 billion or so for a small number of families and their charitable foundations. Before starting Eastrock 12 years ago, Graham worked at two other investment firms. He started his career by co-founding the independent Wall Street research firm Medley Global Advisors. Graham graduated from Yale with a BA in ethics, politics, and economics. He is a member of the Council on Foreign Relations and serves as co-chair of the Sohn Conference Foundation, which funds pediatric cancer research. Our mutual friend Josh Waitzkin, who introduced us, and you should look up Josh Waitzkin if you don't know who he is. I'll give you a hint searching for Bobby Fisher. Josh calls Graham, quote, the tip of the spear in the realms of talent tracking and judgment of human potential in high stakes mental arenas. End quote. That is a mouthful. But Graham, as I've gotten to know him over the years,

is more and more impressive with every encounter that I have with him. And if you want to hear more from Graham, ideas, his thinking, frameworks, everything, you can sign up for his monthly email newsletter at grahamduncan.blog. What is an unusual habit or an absurd thing that you love? So Tim, I wear the Subpac wearable physical sound system while I commute on the subway to my office and sometimes I wear it while I work at my desk. You strap the system to your back and chest and it lets you feel the vibration of music through your whole body. Music producers, gamers, and deaf people are the primary users. I find the full body experience of music makes listening to music or even a podcast that has a lot of bass

more of an immersive somatic experience rather than just a conceptual head thing. If you could have a gigantic billboard anywhere with anything on it, what would it say and why? So I have two candidates. First, it's not how well you play the game. It's deciding what game you want to play. That's by Kwame Appiah, who's a philosophy professor at NYU.

And I like it because it separates striving from strategy. It reminds me to take a macro view of whatever I'm doing, like in a video game where you can zoom out and you suddenly see you've been running around in one corner of the maze. It loosens my relationship to the game too. It's the game of the game, helping to separate having ambition from being ambitious or accessing hustle without actually becoming a hustler. Another quote that I really like is from the Buddhist novelist George Saunders, who said in an interview with The New Yorker that he has an image of people's nectar in decaying containers.

And Buddhists like Saunders think everyone has a Buddha nature, that good core of your being. People sometimes lose track of it, but it's there. I think it's such a good assumption to have about everyone, even if you're wrong sometimes, but it's there. I think it's such a good assumption to have about everyone, even if you're wrong sometimes, that that's there. And I also love that image of nectar in decaying containers. It helps me visualize the stream of Buddha nature flowing through all the lovely, flawed, living and slowly dying creatures that we all encounter every day. I sometimes get this glimpse of how my three-year-old daughter's

three-year-old self is so temporary. Buddhists like to say we're all on fire, and it's so beautiful to sometimes tune in and just see the flickering. What are one to three books that have greatly influenced your life? So the psychiatrist Sam Burundis has a book called Making Sense of People that's had a huge impact on my thinking. And I sometimes give up a copy to people who are building a new team and doing a lot of hiring or even a friend that might be deciding whether or not to get engaged. As part of my role as an investor, I interview 400 to 500 people a year to decide whether to hire them or invest in their various startups or investment funds. The most useful mental model I've found to help me understand what makes people tick is the one that Brundis describes eloquently in his book. The model is called the Big Five

or OCEAN. And the O stands for open-minded. The C stands for conscientious. The E for extroverted, A for agreeable, N for neurotic. And the academics who developed the model clumped every English adjective that could be used to describe somebody into categories, and then they reduced them to as small a set of factors as they could. So if lots of people agreed they could call somebody both gregarious and outgoing, then they decided that was the same thing. And they kept reducing that down until they got, say, extroversion as a primary factor. And in the academic literature on personality, the big five is like the equivalent of gravity. There have been thousands of studies. And it's considered much more statistically accurate than alternatives such as Myers-Briggs.

And so if you want to picture it, like for a high open-minded picture, Leonardo da Vinci. For a high conscientious, picture Robocop. For high extroverted, picture Bill Clinton. And for the opposite, high introverted, picture Obama. For low neuroticism, picture the dude from The Big Lebowski or any stereotypical Californian. And for high neuroticism, picture Woody Allen or Kanye West or most New Yorkers. I could pre-associate about the Big Five, but I'll leave it there. If you want more, then check out Sam Baronis' book. And Scott Barry

Kaufman is also obsessed with the Big Five and writes a bunch of useful stuff about it. There are two other mental models that have greatly influenced my thinking about people and teams. The first is Harvard professor Robert Keegan's model of adult development. Keegan argues that adults develop and make sense of reality in five discrete phases. He lays out his theory in his 1994 book, In Over Our Heads, which is unfortunately not available on Kindle, but is available in paperback. And the title, In Over Our Heads, is a reference to how the vast majority of adult Americans are at the socialized stage of development. He calls it level three. They have difficulty taking other people's perspectives and they tend to follow assumptions given to them

by society as opposed to assumptions they freely choose. And he points out like in modern life that many activities such as parenting benefit if you can set boundaries and not care what your kid thinks. You need to direct them in doing what you think they should do. I feel like I sometimes see what I imagine to be socialized stage parents who are afraid of, they're almost afraid of their kid on some level. They take what their kids think too seriously and they want to be their friends first and parents second. When I'm interviewing somebody, there's something that can feel a little bit icy when you're interacting with self-authored people because they aren't sourcing their approval from you. There's something about the tone of the interview that is distinctive. And to try to make

this more concrete, there's this amazing example in chapter nine of In Over Our Heads where Keegan describes a couple who are both operating from a self-authored mindset. And it's a very distinctive description of the way they make sense of each other and of being married. It totally reminds me of one of Tim's podcasts with Laird Hamilton and Gabby Reese, where Gabby is describing the way she relates to Laird and to their marriage in a way that to my ear is super unusual, self-authored way. For people who are interested in learning more about the model, I recommend Keegan's later book, Immunity to Change, where he describes the model briefly

at the beginning of the book. I'll read a quick excerpt just so people have a feel. Having a socialized mind dramatically influences the sending and receiving of information at work. If this is the level of mental complexity through which I view the world, then what I send will be strongly influenced by what I believe others want to hear. Let's contrast this with a self-authoring mind. If I view the world from this level of mental complexity, what I send is more likely to be a function of what I deem others need to hear to best further the agenda or mission of my design. Consciously or unconsciously, I have a direction, an agenda, a stance, a strategy, an analysis of what is needed,

a prior context from which my communication arises. The self-authoring mind creates a filter for what it will allow to come through. It places a priority on receiving the information it has sought. Information that I haven't asked for and which does not have obvious relevance to my own design for action has a much tougher time making it through my filter.

It's easy to see how all of this could describe an admirable capacity for focus, for distinguishing the important from the urgent, for making best use of one's limited time by having a means to cut through the unending and ever-mounting claims on one's attention. This speaks to the way the self-authoring mind is in advance over the socialized mind. But the same description may also be a recipe for disaster

if one's plan or stance is flawed in some way, if it leaves out some crucial element of the equation not appreciated by the filter, or if the world changes in such a way that a once-good frame becomes an antiquated one. In contrast, the self-transforming mind both values and is wary about any one stance, analysis, or agenda. It is mindful that powerful though a given design might be, this design almost inevitably leaves something out. It is aware that it lives in time and that the world is in motion and that what might have made sense today may not make as much sense tomorrow. Therefore, when communicating, people with self-transforming minds

are not only advancing their agenda and design, they're also inquiring about the design itself. Information sending is not just on behalf of driving, it is also to remake the map or reset the direction. Someone wants to hear how a person sounds when they make sense of reality at the self-transforming stage, then I direct them to listen to Tim's early podcast with Ed Catmull, the Pixar founder and president. The loose but

strong grip that Catmull has on his own beliefs, his fluid and flexible relationship to time, there's a slightly ephemeral quality and comfort with paradox that comes through in the interview. And in the interview, when Tim's interviewed with him, he's actually a bit of a difficult interviewee and he feels a little hard to pin down at times. For instance, he refuses to answer Tim's question about what he would tell his 20-year-old self because he says now he has a way of understanding that his 20-year-old self simply couldn't understand. This is all very consistent with a self-transforming mindset, which happens later in life for most people if it happens at all. As an example, it would surprise me to hear Catmull say or think any version of, quote,

I'm just trying to stay relevant as he gets older. And from one perspective, he might be losing ground versus younger people in his industry or he fails to get his phone calls returned. But his way of making sense is likely that he gets to define who or what is relevant, not his peers in Silicon Valley or the movie industry. One last self-transforming example I would give is the voice of the narrator of the poem Parable by Louise Gluck.

If you Google it, she's really amazing. The third mental model that I find myself recommending lately is not in a book but on a slightly obscure website called workwithsource.com. And it's based on a European management consultant who studied hundreds of startups and realized that even when there are multiple co-founders, there was actually always, in every case he found, an actual single source, the person who took the first risk on a new initiative, even if that risk was only picking up the phone and calling the other co-founder.

And he argues that that source maintains a unique relationship with the gestalt, what he calls the gestalt of the original idea, and that person has an intuitive knowledge of what the right next step for the initiative is, whereas others who join later to help with the execution often lack that intuitive connection to the founder's original insight.

And these guys argue that many organizational tensions and power struggles actually often revolve around lack of explicit acknowledgement of who the source of the initiative is. I was talking about this with a prominent angel investor recently, and he had found that consistent with his sample of startups. And he noted that many founders seem to hire friends as co-founders more to quell their own anxiety during the early, highly ambiguous days of a new company than to fulfill a specific role. This can work fine as long as everyone is clear on who the source is. And what's a little paradoxical here is that the responsibility to fully own the role of source rests in large part with the source themselves. Handing off the source role of an initiative to another person is possible but extremely difficult, and it's often mishandled. And these guys note that a key to a successful transition is for the original source to actually move on and allow the new leader room to move. I was speaking with an investment manager about this, and it was consistent with a study he'd done of stock performance following founder CEOs departing their businesses. And he found that any subsequent positive stock performance was correlated with the founder completely leaving the board rather than hanging around to mentor the next CEO. So through that lens, Gates remaining on the Microsoft board during Ballmer's tenure may have contributed to subsequent lackluster stock performance and Ballmer's inability to

kind of exert his own creative vision, whereas Ballmer leaving the board has allowed Satya Nadella to fully assert his own creative vision. I encounter this dynamic myself sometimes in running a multifamily office where we manage money for Forbes 500 families, and second and third generations sometimes struggle with how to relate to the original patriarch and the, quote, source of their wealth. In my observation, it's often the responsibility room for real

transition is in the hands of the original source. It's, um, the lesson from George Washington's song in the Hamilton musical as Washington declines Hamilton's plea to run for a third term. And he sings, we're going to teach them how to say goodbye. What purchase of $100 or less has most positively impacted your life in the last six months or in recent memory? So I recently bought the Finis, F-I-N-I-S, swim paddles. They somewhat magically lengthen out my freestyle stroke. And when I combined them with some fins, I use the ones from Cressi, C-R-E-S-S-I. It feels sometimes like I'm almost flying through the water. For non-swimmers, I highly recommend the canned sardines from Matiz, M-A-T-I-Z.

I feel like one of my proudest accomplishments as a dad is that my two younger kids eat sardines with me most mornings for breakfast. They're super high protein, high good fats. There's no need to supplement fish oil. And Matisse sardines aren't fishy. I usually add avocado with salt and lemon, and the kids love them. And I often alternate the sardines with canned wild salmon belly, which they call Restreka, R-E-S-T-R-E-C-A, from the company Vital Choice. The bonus on both of those is that when the zombie apocalypse comes,

you'll have canned food ready to go. How has a failure or apparent failure set you up for later success? Do you have any favorite failure of yours? I have so many failures. I'm just going to pick one. In my role in investing in and seeding investment firms. I do really extensive reference checks on people in order to try to accelerate the process of building mutual trust with them. And I should note that I have a somewhat oddly specific aspiration to be the best in the world or among the best in the world in terms of being able to really do a reference on someone.

I feel like it's a real art form to gather private information in the form of multiple perspectives about how someone has played a repeat iteration game in the past and then try to accurately project how they're going to play in the future. I had to find success as gathering enough honest perspectives on someone to mimic how I would know someone if I had sat next to them at work for five years. At East Rock, we try to do references in person and it's a huge time investment. In late 2007, I was about to back a firm, and we conducted a final reference check with the investment manager's former boss, who was quite negative and skeptical about his former analyst. I remember I asked him what percentile the analyst was in terms of all the analysts who'd ever worked for him, and he said top 60 percent, which I thought I misheard at first, and I've never gotten that response again in a reference. And it surprised me, given that the analyst had given me this guy's name as a reference, it wasn't an off-list reference, it was on his list. And it made me pause on proceeding with

the investment, which then proceeded to work out amazingly well as the financial crisis unfolded. I had a lot of regret about the size of the profits I missed. Later on, it emerged that the reference source may have had an agenda to sabotage his former protege's new firm. Then several years later, I was evaluating another investment manager to partner with. And toward the end of our diligence process, I got another reference, not quite as negative as that one, but it was mixed. But I felt like at this point, I was better able to hold multiple perspectives simultaneously

without experiencing cognitive dissonance. It's like the state of negative capability that Keats referred to as useful to writers. And this time, having those mixed data points only made me do more work and I gained even more conviction in the character and competence of the investment manager. And that investment has ended up being super profitable.

And I think absent my earlier failure, I wouldn't have had the ability to see the reality of the situation. And it also just helped me appreciate something I try to do, which is I try to hold people's perspectives with a light grip, which is the knowledge that they and I have very incomplete maps of reality. What are bad recommendations that you hear in your profession or area of expertise? So I think people massively overuse the term hedge fund. They fetishize it a little too much. It reminds me a little bit of a similar issue that Ray Dalio found when he used the word

depression in 2008 to describe some of the underlying dynamics in the economy. He found that his readers had too much baggage with the word, So he switched to using the word de-process. And Yuval Harari makes a similar kind of reframing move by referring to us as sapiens because we have so much baggage about being human and being in the center of the species, the most important species. And in a similar way, I think people now have way too much baggage with the word hedge fund the press and the managers themselves have made it almost jump the shark and I've been telling people lately I think we should start using H structure

or something like that to instead capture the concept of incentive compensation I don't think it's useful to see a hedge fund or a product or even the hedge fund industry because these are just temporary collections of flawed brilliant people who in any given

year decide to make a sequel to the movie they made the prior year. The only product is the set of future decisions that the portfolio manager makes. If they get divorced or depressed, if their second in command leaves, the, quote, product completely changes. And I think thinking of it as a product ignores the reality that the only source of stability is actually whether the mindset of the team leader is resilient or even anti-fragile, which is the Nassim Taleb's thing about actually getting stronger with volatility rather than just enduring it. When you feel overwhelmed or unfocused, what do you do? So I asked myself, what would be the worst thing about that outcome not going the way I want? I had actually started using it out loud with my kids. And recently, my eight-year-old

daughter started asking it back to me, which was karmic full circle. I really like to be punctual, and we were late to drop her at school. And I was impatiently hurrying her along. And she asked me, Dad, what exactly would be the worst thing about being late? And in the moment, it completely shifted my mindset. I like the question because it often surfaces a hidden assumption, in this case, maybe some subconscious script of I'm playing the role of father and our family meets our commitments or some version of that. And another good related question is Byron Katie's thing about could the opposite of your story be true? I think that question serves the same role. In the last five years, what new belief, behavior, or habit has most improved your life?

I've begun swimming most mornings, and I find it often shifts my mindset for the entire rest of my day. Some swimmers talk about this concept of water feel, which is getting a grip in the water and pulling your body past that point instead of ripping your hand through the water. Ripping your hand through the water moves you forward, but it's a lot less efficient and it's less graceful. And I really like David Foster Wallace's speech, this is water, and where he's making the point that so much of life is water to us. We're swimming in it. We can't see it because we're either in a hurry or not awake to our context. Or in Keegan language, we are subject to it.

And when I stop to really feel the water before I pull, it shifts my way of being from one of kind of thrashing towards the end of the pool somewhat mindlessly to a more effortless flow of working with the reality of the water where I am. What advice would you give to a smart, driven college student about to enter the real world? So lately, I've been thinking about careers through Dan Siegel's model of mental health, where he says, picture a river flowing between two banks where one side is chaos and the other side is rigidity. And Dan points out that mental illnesses all reside on one bank or the other. Schizophrenia is on the chaos side.

OCD is rigidity. And basically, healthy integration is swimming in the middle of the river, is his argument. And most college students have started life closer to the rigidity bank, is my observation. And over the course of their careers, will experiment with swimming toward the middle. And I've come to think of the lane right next to rigidity, the rigidity bank, as an appropriately conventional one for when you're in your 20s. And you're kind of acquiring the skill of refining reality. It's a place to swim where it's important to learn the jargon of an industry,

an apprentice under somebody, to develop judgment and discover your own zone of genius. I think swimming in the middle lane happens most often in people's 30s or 40s. It's a stage where you begin crafting your own language for what you do. As an increasingly strong poet, you make your craft your own. You view your life as more self-expression than simply playing out other people's roles for you. And then some small percentage of people will paddle over to the lane next to chaos, which is a place where you find novelists like Robert

Persig and David Foster Wallace, investors like Mike Burry or Eddie Lampert, or entrepreneurs like Steve Jobs and Elon Musk. And I experience them as consistently asserting reality through powerful storytelling, while always bearing the risk that their egos grow too big and their creative narcissism gets too well defended. They lose situational awareness and they basically lose their feedback loop with reality. I visualize them almost flopping onto the bank of chaos.

And so if you look at it through this lens, then Persig's wrestling with sanity towards the end of his life, Steve Jobs' magical thinking about his illness, and Eddie Lampert's Anne Randian framing of his investment in Sears may have all been examples of these guys losing their feel for where they can mythologize to the point of bending our collective reality, and then they suddenly briefly appear crazy. I think Musk in particular drives hedge fund managers up the wall as half of them are short as shares because he exudes so much promotional hucksterism as he asserts reality,

and half of them are long because he's actually thinking on a 100-year timescale. And it's very confusing. At Eastrock, we always say that if you want to have variant perception, it helps to be variant. And I remember interviewing Mike Burry, Steve Eisman, and all the other somewhat fringe, somewhat variant investors who were shorting subprime mortgages in 2006. And basically all the characters that Michael Lewis captured so accurately in the big short. And the housing bubble is obvious in retrospect, but at the time, almost everyone thought they were completely smoking dope. And the current crypto scene, the cryptocurrency scene, reminds me a lot of the subprime short ecosystem, because the opportunity

attracts the most or the more variant players who have nothing to lose from disrupting the status quo. So in crypto, you've got all the libertarians and the unemployed macro hedge fund managers and all the kids. There's this great quote by one of the characters in Tom Stoppard's play Arcadia that the crypto guys like, which is, the future is disorder. A door like this has cracked open five or six times since we got up on our hind legs. It's the best possible time to be alive when almost everything you thought you knew is wrong. I think that mentality of saying,

bring it on to chaos, that now is the best possible time to be alive, to, quote, learn to love the rain, as Josh Waitzkin says, it's really hard for people who have succeeded in the status quo context. And so I think, you know, Bitcoin could just be a bubble due to QE post the financial crisis, or it could be a change in how

we organize human activity at the level of the internet itself or both. And I'm at the moment trying to hold both perspectives without needing to decide yet, trying to stay, I think of as an open chair instead of striving for closure. I'll finish up the career question with one last quote from the very self-transforming Charlie Munger, who at 93 has no filters left, and he has more wisdom per sentence than almost anyone I read. He says, I've noticed in a long lifetime that the people who really love you are the people where you scramble together with difficulty and you've jointly gotten through. And in the end, those people will love you more than somebody who just shared in an even prosperity through the whole thing. So this adversity that seems so awful when you're scrambling through actually is the sinecure of your success, your affection, every other damn thing.

The idea that life is a series of adversities and each one is an opportunity to behave well instead of badly is a very, very good idea. And he says, and it works so well in old age because you get so many adversities you can't fix. So you better have some technique for welcoming those adversities. Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is five bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun for the weekend? And Five Bullet Friday is a very short email

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