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The Daily Stoic

15 Apr 2023 · 1h 19m

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Molly Bloom on Trusting the Process and Making Daily Progress

In short

In this episode of The Daily Stoic, host Ryan Holiday interviews Molly Bloom, a former Olympic-class skier turned entrepreneur and author. This conversation is the second part of a two-part series, focusing on themes of self-interest, progress, parenting, and personal transformation. The discussion draws from Bloom's unique experiences, including her past in high-stakes poker and her journey of self-discovery.

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0:00The world is full of tours. But you don't choose a Toyota truck to follow the beaten path. You choose it to find the places in between. The detours, where each adventure pulls you toward the next. And wrong turns turn out right. So why would you ever take a tour when you could take a detour? Toyota Trucks. my family owns a 2023 toyota 4runner and honestly it's my favorite vehicle that i've ever owned around town it's smooth and reliable but where it really shines is on our trips into the back country we've taken it on backpacking adventures to colorado new mexico loaded up with gear and never had to think twice about whether it could handle the terrain that's what toyota trucks are built for off-road confidence rugged durability and the freedom to explore toyota has a long history with the outdoor community and they're committed to helping more people get out there and experience what nature has to offer.

1:00From remote trails to scenic byways, Toyota Trucks empowers you to take the detour, roam freely, and discover places that still feel wild and untouched. And they're not just making great trucks, they're working to expand access to adventure so more people can connect with the outdoors and pass that passion on to the next generation. Discover your uncharted territory. Learn more at toyota.com slash trucks slash adventure dash detours. That's toyota.com slash trucks slash adventure dash detours.

1:30Welcome to the weekend edition of The Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal, and most importantly, to prepare for what the week ahead may bring.

2:23Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. I read Molly Bloom's book, Molly's Game, in preparation of our interview several months back. And then I didn't get to watch the movie until after we talked. And I loved the movie so much, written by the great Aaron Sorkin. And then I read some interviews that Molly had done and some press coverage of it. And I thought, you know what? I got to talk to this person again. I didn't explore everything I wanted to explore in that first interview. And so I said, hey, Molly, when are you coming to Texas? And it turned out she was going to be in Texas in early March for a speaking gig and our schedules lined up.

3:10And I said, you know what? We just built out this amazing new studio. I know you just did remote, but come to the painting porch, do the studio. do an in-person version. I think it will go even better than the first time. And she very graciously agreed. And that is what you are going to listen to today. Again, you can check out video of the studio of today's episode at youtube.com slash Daily Stoic Podcast. You can find clips of it on social as well. Molly's Game from Hollywood's Elite to Wall Street's Billionaire Boys Club, My High Stakes Adventure in the World of Underground Poker is a riveting read.

3:47The movie Molly's Game, also fantastic. Don't want you to think this is just the story of a poker player. She was an Olympic skier, one of the best in the world. An injury changes the trajectory of her life. She makes a lot of mistakes, does some illegal things, gets addicted to drugs, doesn't recognize the person that she's become. Something I related to is my sort of ambitious early 20s. But then facing a very lengthy prison sentence, gets sober, turns her life around, comes to actually, I think, become a very fascinating ethical and moral person as the book explores and the movie explores. And as we explore in today's interview, I think you're really going to like this conversation.

4:31Listen to part one. Obviously, there's some signed copies of Molly's Game at thepaintedporch.com. I'll link to that in today's show notes because Molly was nice enough to sign them. She left with a copy of The Girl Who Would be free for her young daughter, my kid's book about Epictetus, and as well as The Boy Who Would Be King, my book about Marcus Aurelius, if you're looking for kids books about the Stoics. But this was a great conversation. I think you're really going to like it. Check out the video of it. Subscribe to the new YouTube channel, youtube.com slash Daily Stoic Podcast. And you can follow Molly on Instagram and Twitter at I'm Molly Bloom.

5:10That's Molly with a Y. Enjoy.

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7:07so i i just did four talks in three days and uh it's a little brutal so i'm like i'm pretty burned out but i was thinking what's weird about it is i don't know what people think when they're hiring a speaker but like i think like they were like oh then you could come and like just talk to the CEO for a while first, you know, like, and I was like, is that a performance? Cause that sort of makes it sound like it's more entertaining than it actually is. But I was like, I'm about to go do something like really hard. I don't want to like hang out first. How do you, as you're here doing a talk, how do you think about like approaching getting up on stage?

7:46Yeah. I mean, I just, I had sort of a similar thing where I was just, I had so many talks in a short amount of time. And then they wanted me to show up to this reception before. And that, you know, and I think, you know, someone hires you to talk, you have a message you care about, you want to be able to really bring it. And some people I think are extroverted by nature. And so the social fills them up. I'm more introverted by nature. I think you are too. And so I think you just have to sort of really guard that energy to some degree. Yeah. Like I was thinking like, I'm not just like a salesperson that's getting up there and giving like my quarterly update on how I'm doing.

8:26Like this is a, this is a, a, a thing that I've crafted over, like, I realized I've been doing it for 11 years now. Um, so I don't know how many that is, but it's like, I see it as like a, a zone that you have to get into. Like, you know, like there's a routine that I do and there's like a headspace that I need to get into. Yes. And I like, I treat it very seriously. And yeah, it's been weird watching how other people do it. Yeah, no, I'm the same. And I think mine also, there's such a sense of purpose and almost catharsis from being able to share these things that I either put myself through or went through.

9:15And if there's at all a chance I can help someone skip that nightmare, you know, or, or especially when I'm speaking to younger people, um, share some of the things that I wish I would have known so much. So there's meaning there. And, and also, yeah, I think like, obviously you are someone who is going to give your full self to something. Well, do you think, I imagine as an athlete, like you, you know, how, you know, the zone you have to get into to like do your thing. And then I think you apply that to whatever it is that you do after that. Yes. And people don't always understand that. Yeah.

9:52No, there's a process. Yeah. What's your process? Um, I like to exercise first. Um, I like to not see or talk like, like, you know, there'll, there'll be like, I remember I did when I gave this talk, uh, to the NFL. It was at the NFL owners meeting. It was, it was the craziest audience I've ever spoken to. It was all the owners, all the GMs and all the head coaches. So it was like 30 billionaires and then, you know, millionaires and then other millionaires. It was a, and you know, these are people you watch on TV every week. But anyways, like they were like, I was the fifth speaker. It was five speakers each doing a 10 minute talk.

10:30And I was the fifth one. And they were like, and we're going to have you all sit here in the front row and then you'll go like one after another. And I was like, are you out of your mind? Like I'm not going to sit and watch four other people perform before me and then just get up and go. I was like, I'm going to be nervously pacing in the back, getting in the right headspace, you know? And so I do, I, yeah, I don't want to like overstate it. Like it's just some like super impressive thing, But I do treat it like a really hard thing that you have to be at your best to do. When I'm about to get on stage, it feels as closest to being on deck for skiing as anything.

11:18And maybe that's just me holding on to my sports background. But that's what it feels like. And I also feel that people are hiring you. They're paying you money. And don't take it lightly. I in particular don't take it lightly. It's like, you know, for me to be at some of these places giving these talks after where I was 10 years ago is mind-blowing. I've watched a video of my first talk. It's recorded and it's so bad. It's so bad. And so I was very glad that it hit me that I've been doing this thing for 11 years. Because, you know, like comedians talk about stage time. They'll go up like – the nice part about like a comedian or something is you can do it badly a lot of times.

12:00Like you can get a lot of reps. I think it's harder. Like you can just sort of only do it in front of the audience that wants you. You can't just like get up and give your talk somewhere. But like realizing that it's a thing that I'm trying to get better at also. And that the other question I get is people go, do you like speaking? And I go, I like getting paid for speaking. You know, like I don't think anyone does. Like I guess there's something. I can't conceive of doing it for fun. It's not fun at all. It's a really hard thing. It is. And I like coming up with the ideas. I don't like getting up in front of 500 strangers and talking to them about, you know what I mean?

12:42Especially with what I do because I'm like, okay, I just got up. Like this is a group of, I don't know, like financial salespeople. And I'm like, let me tell you about an obscure school of ancient philosophy. You know, there's like a, it's, it's definitely like, yeah, it's a, it's a risk. It's like a creative risk each time. Right, right. Cause they're expecting a sales trainer more, you know, or like. Yes. Yes. Or you're just like the, the conference is like, they booked you at 8am in Las Vegas, you know, and nobody wants to be there. they're all there for work and then you have to like own that audience.

13:23That's like you're on the razor's edge for sure. For sure. So what are you talking about here? So here I'm talking about risk, resilience, and reinvention. Oh, okay. And do you do the same talk every time? I don't. I use a similar delivery system. So I use the story. Yeah. But I'll have a pre-call with the company. I find out what matters to them, you know, and then I figure out how to sort of customize these different experiences that I've had. Yeah. these into what they care about, whether, you know, they care about the customer experience or risk or resilience or, um, sales or whatever it is.

14:11Um, I just try to mold my, fit my story into that as long as it works. If it doesn't, like I'm really honest with them, you know? It does feel like, yeah, you, you took whatever the sort of skills you learned to compete at an elite level in sports. And then whether you're creating poker games or giving a talk, that's, that's the sort of basis that you build your stuff on. Yeah. And then I would add also, I think as influential as my sports career was as a growing up with a father who's a psychologist Yeah. And then being at a game, which is so largely rooted in psychology, was massively influential to me.

14:58And so I think from a very young age, I have been very focused on trying to understand humans. So you sit and you think about what the people on the other side, whether it's the audience or the customer, like what do they want? What do they need? How are they interpreting what you're doing? Is that sort of where you start from? Yeah. And I think that's a great place to start from. And then, you know, it depends if you're dealing with a large group of people. I think you focus on larger themes. But when it's more specialized, for instance, when I, you know, I blew my life the hell up and I didn't really have very many options.

15:37And so, you know, when I found myself like, as I think we talked about this the last time, I'm a convicted felon, millions of dollars in debt. I'm a social pariah. What do I do? Yeah. Well, I guess you write a book and try to get the, you know, one of the rock star screenwriters to write the movie. And so, you know, before I sat down with Aaron, I did as much research as I possibly could. Because not in an inauthentic way, but in an authentic way, I want to tell him a story that he's going to care about. Sure. And so that's a very different pitch than say if you were pitching to Michael Bay. Yeah, sure.

16:14And so I think just trying to understand people, what they care about, who they are, and then kind of trying to find the connection points has been a really useful strategy always. It is interesting that people don't really think about that. When I talk to people that are pitching a book, they've spent a lot of time thinking about what they want to say, what they want their book to be, why it's important to them, and then spent effectively no time thinking about the person on the other side of the transaction that they're hoping to make. And not even have they not thought about the specific person.

16:54They haven't even thought about generally, who are those people likely to be? Where do they live? Are they male or female? What age? Like, they're just sort of like, oh, obviously the people who are acquiring books or, you know, customers that I want to reach, they're like me. They care about the same things as me. You know, they have the same incentives as me. And really, no, you have to stop and go, who are these people? What do they want? What do they want to hear? And it's not that you lie to them, but you think, how do I take my pitch and I tailor it to them so it's clear that we would work well together or that we would accomplish what we both want to accomplish by working together.

17:37Yeah. People only want what they want. Yes. So you have to figure out how to get them to want what you have. Yes. There's so few people in the world that are just so undeniably fascinating that they can just write a book completely about themselves and give you nothing and it can still work. Or what I, I'm like, look, these people hear good ideas all day. That's their job, right? Like they hear good ideas, but why do they pick one good idea over another good idea, right? It's that one feels more likely to be successful than the other, right? Like it's a business, right? And so when you think about what that person is trying to do, how, you're not really trying to convince them that you have a good idea.

18:18You're trying to convince them that if they back your idea versus this other idea, they will be more successful. They'll win. Yes. Right. Yes. And it's both empathy and self-interest. For sure. I don't think you can ever go wrong starting to engage in a really, in a lifelong pursuit of how humans work. Yes. That's one of the laws in the 48 Laws of Power. Never appeal to mercy or gratitude. Always appeal to self-interest. And if you understand what the self-interest of the person on the other side of the exchange is, you're going to be starting from a much more conducive place than if you're just thinking about what is important to you.

19:04Yeah, absolutely. I mean, if you look at the way the human mind works, most of our decisions, as much as we like to be, you know, say that we're stoics and say we're logical. We're not rational at all. No, we are emotional people. Emotions drive our decision making. Yeah. And so does self-preservation. So I think all this stuff is really important. And then I think that some people get this, but they make it almost too mercenary. I think the third part is to get there as authentically as you can. Yeah. And I guess that's where empathy comes in. Yeah. Well, it's also realizing as important as self-interest is, identity is also a factor.

19:59and nobody wants to identify as a totally self-interested person. Right. So you have to figure out a way that you tickle the impulse of self-interest without being so uncouth about it that you actually have the opposite effect. Yeah. So you don't turn into like a sociopath. Yes. Or make them feel like that. Right. Well, yeah, I remember reading in your book, Like even just how you, like you, you had, you understood why people were playing poker and what they wanted out of the games. And like the, the actual playing of the cards was like almost the least important of the thing. And so the location was important and the people who were dealing and who the other players were.

20:46Like you understood what the experience that people wanted out of the thing was and you built around that. Yeah. I mean, I think the most basic law, if you want to just really simplify human nature, people really want to avoid discomfort as much as they possibly can. And they really want to pursue pleasure. Yeah. And so how can you imbalance that ledger sheet for them? Right. You know? And even down to, I got more, you know, the thought process became more sophisticated. So you can't always control for people to win at the games, but actually you kind of can a little bit more. And the way that I was able to do that is you seat that table with people who have really similar playing styles and similar skill sets, right?

21:40And then you are kind of controlling for people to win as opposed to letting really good players come in, you know, because the pros were offering me the sun and the moon and the stars. Right. Right. But if people are coming in feeling like they're getting taken advantage of. Well, if they lose every time, they're not going to come back. Right. So being really meticulous. And even if it means not having a game, if you can't seed it correctly. Right. And just playing that long game. And so then not only do you have the beautiful candles and the staff of people who've memorized your food order and your drink order and make you feel seen, heard and remembered and this penthouse suite and all the details.

22:29Now you're also in a situation where you believe that you can be effective at this table and that eventually over that year, you're going to feel the dopamine of the win. Sure. That's really interesting. Yeah. And obviously, Las Vegas is the king of this. Like how do they reduce discomfort or guilt or distraction or in other cases ramp up the distraction? Sort of what are the points that people leave, right? What are the points that people decide to take their money off the table? And how do you intervene at that moment? Yeah. So that's a challenging one. But I think one of the reasons that I was able to be so successful is because even Vegas can't control for how the table is seated.

23:24Sure. Right. And so I think people don't understand just how perfected social media has been in sort of understanding these same very human emotions and that the amount of skill and expertise and psychology at play that's making you want to spend time on this thing. And that's probably why you should stay clear of it as much as humanly possible. Well, yeah. I mean, especially if it becomes detrimental to your life. And I think you could argue that we are seeing that. Yeah. Yeah, yeah. I never, well, it's interesting. So you almost never feel better. Right. After you spend time on social media.

24:11So how do they get you coming back? That's sort of the genius of the technology behind it. It's like drugs are gambling. because you are getting a dopamine hit because I guess there's reward for social or for sort of looking at social situations. I don't really know what the neuroscience is, but then there's a cost to it too because you need more of that. What's the variable rewards? Sometimes it's good, sometimes it's not. Sometimes you get a message that changes your life. 99 % of the time you don't, but you're like, I got to check because there could be one life-changing thing in here. I also think that things like social media or Netflix or whatever, anything that can take you out of the thinking mind.

25:01Sure. Because the thinking mind can be really brutal. And so even though it's this distraction that brings you out, like all of a sudden you're focused completely on something else. You're not listening to the voice in your head. You're not listening to the anxiety or whatever. But then now you've filled your head with some other stuff. that's not necessarily positive. And you're thinking like, oh my gosh, like, what is my life? I'm not on a boat in Portofino. I don't, you know, like my kids aren't dressed perfectly and I haven't made some like, oh, you know, Instagrammable feast for them or whatever it is that you've consumed that like now makes you feel like you're less than.

25:41So again, you know, Pema Shadrone talks about the babysitters, these things that we do to distract us from the thinking mind. And that's why one of the reasons why I think meditation mindfulness is so important so that you can start to control the thinking mind. So you're not just taken by it. So you can have a process for anxiety or the inner critic or the racing mind, start to calm that environment. And then you don't need these things that, these places of refuge that have a cost as much. Right. So instead of six hours of mindless, you know, Netflix to relax, you can just have three minutes of just intense focus where you're like, I'm in charge of my mind.

26:27Yeah. I can turn it off at will. And that's like a super powerful muscle to have. It is everything. If you can manage what you focus on, what you pay attention to, if you hone the skill to be able to bypass the things that stress you out or whatever, when you start to manage the mind, then it's all possible. Productivity, ceasing procrastination, anxiety, insomnia, all these things. And I'm speaking from experience. Yeah. Um, and you know, I, I just, I had a kid a year ago and it feels like when you have a kid, your amygdala grows to like 10 times its normal size. So I'm kind of on this, like this path to like now try to manage my mind under these circumstances.

27:22So it's, it's, you know, it's even more challenging. But, you know, before I had Fiona, I can tell you, I had gotten to a place where almost no matter what the circumstances were, I could find stillness and peace.

27:40Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastro County, I drove my car about halfway down the dirt road that we live on. Thought this isn't going to work. Stopped, parked it, walked the rest of the way home, borrowed my wife's car, drove in Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields.

28:20and on the unpaved roads like the one that I lived in. We got to go deep into the hill country's wild beauty. We've driven all the way out to East Texas. We've driven it across the country. And by we, I mean not just my wife, but both my kids who I drove home from the hospital in that truck. Toyota trucks are built for those who understand that the best adventures happen when you're willing to veer off course because you never know when you'll end up on a Toyota adventure detour. And of course, this is stoicism, too, because every detour, every obstacle is an opportunity. But it's helpful if you can handle the difficulty inherent in that.

29:00If you've got the resilience and the right companion to make it wherever the road takes you. Discover your uncharted territory. Learn more at toyota.com slash trucks slash adventure dash detours. You hear that? That's not just a Toyota truck. That's the sound of no crowds. No alerts. No distractions. And no telling what you'll find next. You know, like a detour. So why would you ever take a tour when you could take a detour? Toyota trucks.

29:46yeah i think what kid like it's easy to have stillness and peace when you have control over the inputs and you have control over the environment right so you're like this is when i wake up this is when i do things this these are the things i don't do and i think what kids do is they blow all that apart and then you have to figure out okay can i do this when there's someone literally screaming in my face. Can I do this on half as much sleep? Can I do this? There's this stoic thing I was thinking about with kids recently. He was saying like, he's like, just stick with first impressions. Right. So he's like, you know, my kid is sick.

30:24He's like, that's it. Not my kid is sick and something terrible is going to happen. Oh gosh. Yes. Or like, you know, my kid's like having trouble going to bed, having trouble going to bed, not, it's going to be a terrible night. You know, like just sticking with like the small interact, like, or my kid is throwing a temper tantrum about X. Like, if I let them win here, you know, then flash forward 30 years, I must have screwed it all up. Right. Like I think so often like extrapolation is the enemy of being a good parent. Yes. That is so wise. I'm going to take that with me. You know, my dad said something to me.

31:11He said this to me at different times in my life. And it's just like, it's the best reminder. The first time he said it to me was when I had that crazy back surgery when I was 12 years old. And I knew I wanted to ski. And the doctors were like, you're not going to ski. and I was so determined to do it, but I had this voice in my head that was like, don't even try this. Like, are you kidding me? You're going to fail. And it was relentless. And so, I mean, I went to my dad and my dad's like, your problem is not that you have this voice in your head. Your problem is that you're listening to it. Oh, interesting.

31:46And your problem is that you're not doing anything about it. So it's like, and I was like, well, what do you mean? What do I do about it? He said, you got to beat it up sometimes, you know? Sure. Sometimes mindfulness meditation works for me. Sometimes I can just practice non-attachment, but when that voice is deafening and loud, I got to go to war with it sometimes. I have to talk back to it and I have to say like, listen, I'm not going to be this person. And I have to do that with the sort of fear and anxiety I feel around being a new mom because I don't want to raise a neurotic kid. So I have to talk back to that voice that's like, oh my God, don't let her eat.

32:24Like, you know, that because then, you know, and, and, and I have to do that a lot. Your dad was super hard on you as a kid. He was. How have you, how has that informed how you're a parent?

32:39So I, at this point, I'm able to separate what was good about that and what was bad about it. What was good about it was I think it's hard to train humans to actually seek or withstand discomfort. Yeah. Okay? And I think my childhood in sports and being raised by this dad who sort of understood that was critical because I developed discipline. Sure. You're in the world. You see how few people are able to develop discipline. Most people really just kind of don't have a threshold for that. Sure. So, and to understand that doing anything well is going to, there's going to be a bit of suffering. My dad called it constructive suffering.

33:21Yeah. What I'm not going to do with my kid, I am not, I don't want her going into the world thinking that her entire value and her worth in this world is based on what she can produce. Yeah. It seemed like your dad saw the success or failure of his three kids as a reflection on him as a person. And that's a really tough thing to put on yourself, but also on little people. Yeah. You know, it's interesting because I think that is generally the case. But I think with my dad, because he's a psychologist and because he sees so many people whose life doesn't work. Yeah. I think he wanted to give us the tools and the skills.

34:13I think he just, and he was an intense guy. Yeah. And was part of it, you know, an extension, a reflection of him and his ego. Yeah, I think unequivocally that is a really hard thing to avoid as a parent. But I actually think he more wanted to prepare us to, or wanted to set us up to, to win in life. Interesting. But I guess it comes down to what is one's definition of winning. Well, that's that it was an incomplete definition. Yeah. And, and I think we're just now starting to realize that the math of success is, is, is a bit different than we originally thought. because it's like, how many ridiculously successful people do you know that are just miserable and are going to get to the end of their life and be like, well, I had a lot of money.

35:05Yeah. It's like, would you like your kid to be good or great? Right? Like, I mean, like a good person or great at something, you know? And it's probably easier to measure sort of greatness, right? Than goodness. I want her to be a good person and I want her to be happy. Yeah. I want her to have a, I want her to be able to be content. Yeah. And to feel, and when I think about the word content, it seems like a simple word, but man, there's so much that goes into to being content. Sure. And I think a big part of that is a purpose, a purpose. Sure. Liking yourself. And I don't think liking yourself comes from, I don't think that's a simple thing.

35:56I think it's, you know, have you been able to be accountable to your core set of values? When you get up in the morning, do you know that, that you can depend on yourself? Sure. You know, Are you a good person? I mean, I think content is a very, very high place to aim for. Yeah. When I interviewed Michael Dell, he had this great acronym. He said, pleased but never satisfied, which to me is a nice definition because I think people think content is somehow like frozen in place. Yeah. But if like never being satisfied is a way to get very successful. Sure. Because you always have to do more and more and more.

36:38I like that. It also makes it impossible to enjoy said success. So the tension is, can you be pleased with what you've done, but still want to do more? Yeah. Yeah. I like that. Yeah. I think that's a really great, accurate way to... It's a good goal. Yeah. I mean, do you think it's possible to like raise kids to be really great at something and not like, and not screw them up in the process? Yeah. Yeah? Yeah. My brother, Jeremy, was number one in the world at 16 years old. Yeah. Mobile skiing. Played, you know, ran a 4-3-40. Played in the NFL. Pretty much had a dream childhood. Yeah. quit sports, found other things that were purposeful, and I don't think he screwed up.

37:37To me, that's the rare thing, right? People who are really great at what they do and not filled with self-loathing or, you know, it's some sort of empty void that cannot be filled. The more disease. Yeah. Yeah. Yeah, yeah. Yeah, because that personality really lends itself. Yeah, it's adaptive. Yeah. Right? Like the person who is never satisfied is obviously going to keep going. What do the Stoics say about the antidote to the Moore disease? Yeah, I don't know. I mean, Seneca has this great line. He says, poverty is not having too little. It's wanting more. And I don't think he means, you know, I don't think he's making light of people who are actually impoverished.

38:23But I think he's saying that you could have a lot and be very poor if all you're thinking about is other people who have more. Right. Or how much more you could do. Yeah. It's like that quote we were talking about from the psychology of money. Yeah. Yeah. And you know so many people like that. I know so many people like that. Yeah. I've never met a person who had a number. You know, like you talk to people, they're like, I have a number. Yeah. I've never met a person who got to that number because the number moves. And whatever they thought getting to that number was going to give them, it never does.

39:04No. But I feel like you realized that at some point because you had this, you were on one trajectory. Well, what I thought about is like, what do you actually want your life to look like? Like, what do you want your day to look like? What do you want your life to look like? And then I think if you back out success from there, it's easier than putting success on a certain kind set of accomplishments. I mean, because you've created your own reality in a sense. I guess. You've created this own, your own like world. Yeah. Yeah. I don't know. I feel like for me it was, it was like, what, what does a really good day look like?

39:42and then if, how close are you to having that day on a consistent basis? Because I mean, obviously life, you're gonna have to do shit you don't like. Of course. And you're not, you don't always get to control what everything looks like. But generally, are you largely in control of your own life or no? And if the answer is no, how successful are you actually? Absolutely. But then, you know, if you don't have that and then someone says, hey, do you want to get paid X to go do Y? You're like, well, it seems dumb to say no to that. If you're like, well, that gets me further away from what I want to do, then it's a little easier to say no.

40:29Like, I hate when I have shit on my calendar. I hate getting on the phone and I hate having shit on my calendar. Those are like my two least favorite things. So when I have days that my calendar is booked or I have to get on the phone a lot, I'm like, this is not a rich life. You know, this sucks. I'm not in control. How powerful am I? I have to go do a bunch of stuff that I don't want to do. Right. I have no freedom. Yeah, exactly. Yeah, but I think achieving that balance, right? Because like, I also know people who are just independently wealthy, have trust funds or whatever. And so they never do things they don't want to do.

41:10And then that's also that sort of directionless person that their life skills start to atrophy a bit. Like, I think we have to get uncomfortable. I think that's part of it. That's right. Yeah. What are the, you mentioned earlier that a kid has to have a purpose or a project. So it's like, what are you supposed to be working on? I think it's really important. So like people retire, people sell a company, they make a ton of money. and now they don't know what they're supposed to do. Not like what they have to do, but they don't like have a thing to do. Yeah. That is, that's a hard place to be. I've seen people do that and I've seen people get really, really, really miserable.

41:53Yeah. I don't pretend to know exactly how the human mind works, but there's definitely something about the mind that proffers from having some sense of purpose and having a place you have to go to gets you out of yourself. Yes. You know, if you want to be miserable, just sit around all day and think about yourself and take your temperature, so to speak. Yeah. You know? Well, constraints are really important. I think you see this like, so someone has started a successful business and now they're like, I want to start the next business. Right. And now all the constraints that were actually really conducive to succeeding the first time, like they had a limited amount of money, they had to get investors, they had to get people's approval, they had a limited amount of time, all those constraints are gone.

42:40So the project becomes really self-indulgent. It takes forever or it never happens at all. Right. And so constraints are really important. And so like, that is something I think about in my life is like, like one of the reasons, like people go, why do you still traditionally publish? I actually think one of the advantages to traditional publishing is that you have signed a contract and there is a delivery date. No question. And it's not like,

43:08it's not your, you're not the only party involved. Yeah. And you need that. No, for sure. Absolutely. If there wasn't that in place, that's why I was so happy I did this, you know, the podcast I did with Film Nation and Sirius. Because like, if I had to just write and develop, I would just get lost in it. No, it's still not good enough. It's still not good. So you need someone to say, nope, we've got a deadline. It's happening today. I know someone that's been working on launching a podcast for two years. Yes. You know? That would be me. It's not going to happen because they don't need it to happen.

43:49And their other stuff has been so successful, it's probably going to be hard for them to be bad at this thing. Like Tim Ferriss gave me this advice. He said, he's like, just, he's like, you have to commit to doing it and you have to commit to doing like at least six episodes or 10 episodes. Like pick a number, do that number and then evaluate at the end of the thing. Yeah. Whether it worked or not. Yeah. You just have to get in, get in the game. Yes. Yep. Yeah. That's something I've been, I've been saying lately. It's like start the clock. You have to start the clock. Yep. You're like, you're thinking about starting.

44:27you need all these things to like so you you haven't started the fucking clock and it nothing matters until you start the clock until you step on that field that's it yes yeah because then once you start the clock then you know if we're extending the sports metaphor like you want to get it done as little time as possible you don't have so many times the shot clock's gonna go off or whatever you have to start the clock yeah people might be watching at this point yes right yes uh and if you don't start the clock i mean the benefit of not starting the clock is that you can't lose, but you also can't win.

44:57Right. Yeah. I mean, writing the Daily Stoic email has been part of that too. It's like, I have to write a certain number of emails per year. Right. I don't think about it day to day because like, I don't do it for the day, but like, it's like I wake up and I know that I have to add to this buffer, you know, because if I don't, I'll run out of them. Right. And so like, I think it's having, having the fit, knowing what you're supposed to do today is really, really important for happiness and productivity and contentment. I can't believe that you write those, that you send those every day. I read them and they're always good.

45:37And I'm like, this seems so freaking hard, but you know what is so cool about doing something like that where you are constantly writing ideas out? It makes you so much better and smarter. Yes. Well, it's about reps. Yeah. I'm sure you saw that with poker. Like if you want to be good at it, you got to play like lots of games. Yeah. That's with anything. I remember when I first started public speaking and I was like, you know what? At least in skiing, when you suck and you're just, you can just train for a while and you're not in front of people and you just suck and then you get better and then you start competing.

46:14With public speaking, you You just have to get on the stage, or at least I did, because I was broke and the movie came out and I needed money and people were offering me money to do it. And the first time I spoke was in front of 5 ,000 people in Vegas and I was so bad. And I was just like, and you get off the stage and you just want to like crawl in a hole. Yeah. Because you just kind of like were bad in front of 5 ,000 people. Sure. But the only thing that ever made me better was just doing it. Yeah. Tyler Cowen, he said this thing once. He was like, what are your scales? Like, you know, a musician practices their scales.

46:50Yes. Knowing what the scales are for your sort of chosen line is the most powerful thing you can figure out. That's so cool. Because then you know how to practice whatever it is that you do. Yeah. Yeah. And you know what you're supposed to do each day, which is practice your scales. I love that. Yeah, I'm writing, the next book I'm writing, it's more research heavy. And Molly's Game was not. Yeah, because it's your life. It was research, yeah. It was going back into stories that I didn't want to go back into. But this is, and it's like really, I don't know really how to do it. And so it feels so chaotic right now.

47:32Sure. But I know from everything else that I've tried in my life that you have to just do it. You have to keep doing it and doing it. And then you find your way. and research, you know, to like find out stories from other people. Like I, your note card thing is helping me right now. Well, I was in the office like a year and a half ago and I was sitting down to write Discipline is Destiny. And I was going through my cards and I was like, there's not a book here. Like, what is this? There's no book here. And I found this card that I wrote to myself. And I said like, follow the process, keep doing your cards.

48:06Eventually you'll find the book. And I think one of the things you get having done a thing a bunch of times is you start to have a sense of like the rhythms of it. And you're like, oh yeah, there's always this part at the beginning where you're like, what the fuck is this? This isn't going to come together. And then you know, you know, you're just supposed to keep going. Yeah. And then eventually it will emerge. You don't know when. Right. You don't know if it'll be amazing or pretty good, but you know, like, if you just keep going, eventually you'll get to the end. Yeah. And I think that I always think about growth mindset.

48:46Yeah. And I think about, um, like that. So Carol Dweck would go into the schools, um, the, like, for instance, she would go to the schools in the Bronx that were, you know, the kids were chronically underperforming in math. and she would start to show them what happens in the brain when you're trying to learn something or you're trying to do something new. And there's this inevitable place in the middle where it feels like you're never going to get there. And it feels like this is not for you and your brain doesn't work this way and you're not going to get the skill or you're not going to write this book.

49:18And she would show them what is actually happening with the neurons and everything. And that if you just believe and you just stay in it a little bit longer, then you get there and you learn how to do the math problem. And then at the end of that year, after she and her educators went in there, that particular school tested like number one in the math districts, you know? And there's just that place in the middle when you're trying to learn something, you're trying to do something. And that's where most people rip court out. Because it's just like, nope, this isn't for me. I'm never going to get there.

49:49It's like when you're cleaning your house and it gets way messier before it gets cleaner. If you're just like, oh, this isn't worth doing and you never get to the other side, you're missing this critical piece of evidence, which is that if you had gone on just one more day, it would have all started to come together. Right. And it always feels longer than you think it will.

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52:44Yeah, there's a law in economics. I'm forgetting what it's called, but it always takes longer than you expect even when you take this law into account. Yes. And when you're like, oh, yeah, okay, this is how it goes. There's always this moment where it doesn't, you're not sure it's going to come together. you're not sure if it's going to work, but that if you push past that, then you figure out, oh, okay, this is a part of, there's always an all is lost moment. Yeah. And then it comes together. And then whenever you get to that point, you're like, why did I think this was supposed to happen so fast?

53:21Yeah. You know, but you're there. Well, because you compare finished things with unfinished things, and it feels impossible to get from here to there. Totally. But if you've done it enough times, you get comfortable being uncomfortable. You're like, oh yeah, this is just that phase. This is the process. Yeah. Like I was, we know this family, they have like six kids and that's like a lot of kids to me. That's a lot of kids to me too. But you realize, oh, the other kids, it would have gotten easier as they went because they'd done this before. Like I don't, like I have a six-year-old and one is about to turn four.

54:00So six is as far out as I know, right? So I don't know how a seven-year-old turns into an eight-year-old, an eight-year-old turns into a nine-year-old. I don't know that eventually, you know, like, and so you realize, yeah, if you've done this thing a bunch of times, you're like, oh yeah, this is just that phase. Right. And understanding someone who's started 20 companies, they know all the phases. Totally. And this is the phase where you fall out with your partners and you all sue each other. Like you start to know all the suite of things that can happen. You're like, this is just one of those things.

54:36Did your life change a lot coming from one kid to having two kids? Yes. Because when you have one kid, when your spouse has the kid, then you don't have a kid. Right. Do you know what I mean? Like you're able to like, you're able to cling to the vestiges of your old life. And then when you have two kids, it's just like everyone has kids all the time. That makes sense. Although the pandemic was huge. So my youngest was eight months old when the pandemic happened. Oh, wow. And we have like, you know, that like little board with the letters where you're supposed to like take pictures like every month.

55:13Like that's like still in his room and it still says eight months. You know, like it's just, that's like, that's like when your watch broke, you know? But so, so it's hard for me to separate having two kids and like the changes that happened from the pandemic. Yes. Because like it forced me to like actually be at home and not be in denial about stuff. Yes. And sort of fully take on all the responsibilities of being a parent and a co-parent. Yes. And in a way that was like, I'm so grateful that it happened because I think I've said this before, but like I didn't, we didn't go, we went places together, but I, we didn't spend time.

55:56We spent like 500 consecutive nights with each other because we lived out in the country and we're like, whatever, let's just, let's just ride this out. Right. But like, so it forced us to like just get really serious about it. Yeah. In a way that like, it's been really good. And the changes have stood. I think so. I mean, now, you know, like for this thing that I just did where I did four talks in three days, this was the, I hadn't spent three consecutive nights away ever. Really? Yeah. So it was a little different. Yeah. But yeah, just realizing that it's here and you have to accept it and embrace it.

56:42And the more that you embrace it and accept it, easier it gets. Yes. Or the better things operate. Yeah. It's like, I think what I'm trying to do right now as a parent, as a single working mom,

57:01I have to be, I'm trying to be completely there when I'm there. Yeah. You know? Sure. Like not, you know, just super present in the moment. And then when I go, I can't leave half of myself there. Yeah. You know, and that's been so hard. I can't like listen to her baby monitor every single second while I'm trying to get in the mode of speaking or whatever. And so I think that's just the part that's really hard. And so I think about like another kid. Yeah. That would seem like you're split even more. Yes. Although I heard when you have three, it's easier because you just, the joke is that you switch from man to man to zone defense.

57:48I'm not having three, so. Yeah, that seems like a lot. I always, I tell my wife, like, we'd have to get like a different car. You have to like have a different kind of house. You know what I mean? Just like it's just three feels like a. It's like a small team. Yeah, it feels like totally. Like with two, with four people, you can be like a regular, like when I see like a family of five at the airport, I'm like, that seems really hard. Yeah. Can't even sit in the same row. No. Yeah. You got to like spread out. Yeah. It's too much. It's too much. It's too much. What, um, how many hours a day do you think you spend working?

58:27Not as much as people think. I'm curious about this. Yeah. Not as much as people think. Like, I usually take them to school in the morning. I usually start writing about like 8.30 or 9. And then I'm usually done by pickup, which is like 3.30, 4. That's a long day. But that's like regular people hours. Yes. Yes. I would have thought with how productive you are that you're like up all night and... Yeah, I hate all that shit. I think people who... I think all-nighters are garbage. I think... They are terrible. People who work, you know, like 100-hour weeks or people who are gone constantly. I think a good portion of that is inefficiency.

59:12For sure. And a lack of discipline. I think it requires more discipline. It requires more discipline to do things within set parameters. Unquestionably. Yeah. What if you're having just a terrible day writing? Do you just then like do research instead? Well, so I was writing about this recently. Like I was sitting down, I was supposed to write something and it like wasn't happening. And it was, it struck me that I just didn't have the material that I needed. It wasn't that like writer's block, writer's block doesn't exist. Not having material exists. And so I was forcing something that I wasn't actually ready for.

59:55Got it. And so to have the discipline to go, okay, actually, yeah, I need to go read. Like I would like to be making forward progress on the draft, but I have to go do the prologue to that. Yeah. That's usually what it is. But then also I think like there's this tension. It's like some days you force it. And then some days you have to go actually forcing it is the worst thing. It's probably like an athlete's like sometimes you push through the pain and sometimes you need the discipline to go like actually know. Listen to the pain. Exactly. Yeah. Yeah. Yeah. Yeah. And there's a cost if you don't.

1:00:36Yes. Right. Because if you hurt yourself worse. Right. Then you didn't save any time. Yeah. Steinbeck has this quote about the false economy of overwork. so if you get burned out or you hate it um you know that's or or just what you're producing is garbage you know are you actually you're not making forward progress you're not working smart yeah yeah so you sent me this text about female stoics yes why were you interested in female stoics because i think uh i think stoicism is fascinating yeah i'm really into it but you don't really hear about female stoics that often i'm sure that they exist but i you know and since you're the the the stoics guy i wondered if i i wonder how much of it is that there weren't female stoics and how much of it is that we were only interested in male stories well there's that Like in the Roman world, most of the women would just get the same name.

1:01:47So it's like Julia Caesar's daughter would be named Julia and then her daughter would be named Julia and then her daughter would be named Julia. And they were just like, they're all Julias. It doesn't matter. You know what I mean? So I'm not sure how, like, I'm not sure how interested anyone actually was in whether, you know. All the Julias had a thought in their head. Exactly. Exactly. Exactly. Although one could argue that that's actually more stoic to not need the attention or the validation or to put up with the indignity and the disrespect, to not need the spotlight. Yeah, to not need the spotlight, but to want to have your own name.

1:02:32Well, no, no, that's not what I mean. But, but like, like there's this great line in, in one of Robert Caro's books where his wife and he were this sort of research team for like 50 or 60 years. And they were, they were actually out here. They were interviewing all the sort of people that Lyndon Johnson grew up with. and his wife was sort of interviewing all these women who lived in the Texas Hill country and just like how the sheer fortitude and strength that their life took, you know, like, and he has this line in the book and he was like, we hear a lot about like the cowboys in the old West, but he says, we don't talk that much about like fetching water from the well with a perineal tear.

1:03:18and you're just like, oh yeah, who was actually the tough guy, right? Like the person going into town and getting in a gunfight or the person who was cooking bread in a cabin on an open fire when it was 100 degrees outside. You know, like the actually the sort of unsung heroes that we don't celebrate in history embody a lot of the stoic virtues more than the people that we do celebrate. yeah or at least uh as much and deserve recognition yeah um did i tell you about my mom when i was growing up so i um i came home from elementary school and i was like i don't want to go to history anymore and she's like why i'm like because there's no history about women yeah i mean i think we heard about betsy ross yeah like she sewed the flag or whatever you know which was like I don't care yeah and so my mom there's this librarian she's really awesome I still remember her name her name was Tina Sekovic and my mom went to Tina and said could we set up a program where Molly can come in and read biographies about women yeah and it was who did you read about

1:04:39there wasn't a lot yeah but I remember Eleanor Roosevelt Joan of Arc who was the female scientist? I have a one-year-old. Okay. I get it. No, no. Representation matters in the sense that it's not that those people didn't exist. It's just that you just don't hear about them. You don't hear about it. And you're starting to hear about it now, but that was a big moment for me. Yeah, that's great. At first I was like, mom, I don't want to go read on recess. Yeah. But then I just did it. And that... And really, that really affected me. Yeah. And, you know, I think we live in a different world now. And I think that we're starting to hear more about, you know, women that did incredible things and whatever.

1:05:32But I think we still have a ways to go. Well, I thought, so Portia Cato, who I talk about in Lives of the Stoics, is like, everyone knows about Julius Caesar. And they know that Brutus assassinated Julius Caesar. but it wasn't until I sat down to write that book that I was like, oh wait, his wife was the driving force of all of it. And you're like, how did this not come up? And then even like the Shakespeare play, she's a major character. She would have been played by a male actor, I guess. But like the idea that there's sort of, I think what your mom actually taught you there is that there's the story and then there's things that are left out of the story and that you have the power to go figure those things out for yourself.

1:06:12Yes. Yes. And that they exist and that you, she showed me that you didn't have to stay within the lines also. Sure. You know, it wasn't just like, because when I remember speaking to my teacher about it and she was like, this is what we teach in history. Yeah. You know? Sure. And it's like, okay, for a little kid that doesn't have a mom like I have, like, okay, I guess this is my reality. But my mom then went in and expanded my world and expanded my reality. And that was huge. Yeah. And if you don't like what you're getting, you can go figure out how to get what you like. Yes. That's the real lesson.

1:06:50You have agency. Yes. Who do you think the most sort of important modern Stoics are? Yeah, it's weird. I mean, I think in the ancient world, it's so much clearer. Like, okay, this person was a Stoic. This person wasn't. You know, I'm reluctant to be like, Like, oh, this person is a Stoic today because I feel like it gets, like when we look at the ancients, we're not that interested in sort of like what was their political affiliation or, you know, we're just able to look at them as sort of this like example. But I think General James Mattis, you know who that is, is probably one of the more interesting ones.

1:07:31He would carry Marcus Aurelius with him like on his deployments and sort of tried to put Stoicism into practice. has been a really sort of interesting guy. But yeah, I don't know who I'm like, oh, this is a modern Stoic. Obviously, James Stockdale is probably the most powerful and clear example. Do you know who that is? So he's shot down over Vietnam. So basically he's a Navy pilot. And the Navy sends him to Stanford to get a graduate degree. And while he's getting his graduate degree, this philosophy professor gives him the writings of Epictetus, one of the Stoics. and he's reading it, he's reading it.

1:08:09And then shortly thereafter, he shot down over Vietnam and he spends seven years in this prison camp where he's tortured. Like that's where John McCain is and a bunch of these other POWs. And he actually says to himself as he's parachuting in, he goes, I'm leaving the world of technology and entering the world of Epictetus. And he saw it as this opportunity to sort of put stoicism into practice, like in one of the worst of environments that a human could do. and it's pretty incredible. Wow. This thing comes out of it called the Stockdale Paradox. Have you heard of this? Uh-uh. So Jim Collins, have you read Good to Great by Jim Collins?

1:08:45No, but I'm going to. It's a great book. We have it in the bookstore. But he interviewed Stockdale before he died and Stockdale was asked by Collins, he said, you know, like, who had the most trouble in the camps? And he said, oh, that's easy, the optimists. And he's like, what do you mean? And he's like, the people who thought, like, we'd be out by June or Christmas or that would be easy or that they were going to be rescued. Those are the people that have their hearts broken. And he said, what I figured out was that this was going to be really hard. It was going to take forever and I might not make it out.

1:09:23But what I decided was that if I did make it out, I would turn it into the best thing that ever happened to me. And that's the Stockdale paradox is this sort of unflinching acceptance of the reality of your situation while still asserting the agency to be better for it. Do you talk about that in your speeches? Sometimes. Yeah. Yeah. Great. Well, what about then Nelson Mandela? Yeah, sure. Viktor Frankl. Yeah. I mean, logotherapy from Viktor Frankl, like the logos is a concept from the Stoics. I think those people are all sort of Stoic adjacent. Okay. And what I try to do in my books is tell stories of people who are representing Stoic ideas as opposed to necessarily doing it explicitly out of Stoicism.

1:10:13Because I think there's more of one than the other. Got it. You know what I mean? Yeah. RBG is a bit Stoic adjacent. Ruth Bader Ginsburg? Yeah, for sure. Although she seemed to struggle wrapping her head around her mortality. Now we're in the mess that we're in. Yeah.

1:10:33which is a general political problem that we have is, uh, old people hanging on too long instead of, uh, ushering in a new generation. Uh,

1:10:46yeah, no, she, she definitely is. She definitely is. And she has some good stuff on parenting. Does she? Yeah. Because like, I mean, when she had a kid, like women weren't supposed to work and, uh, and she and her husband figured out like a really interesting balance. Okay. I think I wrote about her a little bit in the Daily Dad book. Now she also got this great piece of advice. Her mother-in-law, as she was marrying her husband, her mother-in-law said, you know what the secret to a good marriage is? And she was like, what? She's like, it helps to be a little bit deaf. I heard that. And that's the secret to her, I think, work on the Supreme Court.

1:11:26How does she maintain friendships with people that she has these intense ideological disagreements with where things get tense and nasty. It helps to be a little bit deaf. I think that's a great stoic lesson. Yes, yes, yes. I've heard a couple of her things, a couple of her sort of philosophical lines and the way that she managed all the contention that surely exists. Yeah. And she always struck me as, I guess, stoic adjacent as well. Yeah, for sure. What are you writing about in the new book? So I'm writing about effective presence. What does that mean? Effective presence is a really, it's a small body of work.

1:12:07There's really only one paper on it, but it's the science of how you make people feel. So is that like charisma? It goes beyond charisma because it is rooted in connection. Interesting. So, and I think I've always wanted to write about this, but I'm never going to write a book with an N of one. Yeah. You know what I mean? Sure. So, like, I've been really looking for the science and the psychology that can support it. Sure. And, you know, I think Effective Presence is it. And so I'm writing that. I'm writing it with my dad, actually. Oh, that's fun. Yeah. Because, you know, his PhD will give me credibility, but more so it's, you know, it's cool to have this full circle moment with him.

1:13:05Yeah. I imagine there were times in your life where you would not have guessed that would ever be possible. No. No, a lot of times, and this has to do with my sort of all-consuming need for freedom. Yeah. But my parents felt like my jailers. Yeah, I know that was true. You know? Yeah. So, I mean, you look at my journals from high school, I never wanted to talk to them ever again in my whole life. Right. But they just had the unfortunate role of trying to contain someone who, with everything I had, did not want to be contained. Sure. And if the containment was going to happen, I wanted it to follow very specific rules and I wanted it to be just.

1:13:52Yeah. And they were human. So there were some inconsistencies and I was not down with that. Please, Fiona, do not be anything like me. Yeah, that was interesting about your story is that obviously you can read in the memoir, you have some strong feelings about your dad, but then it doesn't feel like it gave way to resentment or grudges in the sense that you're like, I never want to talk to this person. Oh, I know. There was that period. But I mean now. Now. It didn't seem to be permanent. Well, we had a real come to Jesus, if you will. So in the movie, it happens in Central Park at the ice skating rink.

1:14:39And his answer is different. In real life, you know, when I finally got the guts to ask my dad, because I was simultaneously angry and devastated because I thought that my dad just liked my brothers more than he liked me. and I was so afraid to ever ask him the question because I guess my fear was that he would say no I know but I could tell that he would you know and so but finally you know I'm about to everyone thought I was going to go to prison um I'm about to get sentenced and and he says I'm coming to talk to you because we hadn't spoken for a year yeah so we were fighting and we sat down and we just hashed it all out everything from childhood you know and then and I asked him I was like I I just don't understand.

1:15:19Like, why do you love my brother so much more than you love me? And we were both emotional. And he was like, I love you so much. I love you every bit as much as your brothers. You were way more difficult than your brothers, which was true. He said, but I think what you're, I think what you're responding to. And I think the mistake I made is I think the world is really hard. I think it's harder for girls and I wanted to make you tough. Yeah. Interesting. And so, you know, it's really hard to ask those questions, to get vulnerable, to go to the places that scare you. And you don't always get the answer you want.

1:15:58But this was one of those incredible outcomes where like, I saw my dad. You know, I saw him as this 29-year-old man who has a daughter who wants to do the best he possibly can for her. and, you know, almost, and he said it was hard for him too. Yeah. Realizing your parents are just people who met. Right. Is both helpful and then also kind of sad. Yeah, totally. Yeah. And then also makes you take, at some point, makes you have to take responsibility for your own life. And what happened to you is what happened to you. But anyway, from that day forward, we started to work on the relationship. And I mean, he's my best friend.

1:16:50He's my buddy. What have you taken out of that reconciliation? I learned a couple of things. I learned, first of all, that you just have to go to the places that scare you and have those conversations. And whichever way it goes, at least you know. Yeah, sure. I think spending a whole life harboring this thing and having a question mark was really killing me. And I can see how you would do that forever. Sure. The other thing that I took from that is it's so rare that one person is purely culpable and the other person is completely innocent. There are the situations that that is the case. Sure. But looking at my responsibility.

1:17:42Even when you were a kid? Yeah. Not placing blame. Sure. But looking at like, okay, I'm a human being, right? I have these two sons who are just yes men. Yeah. And they're like, daddy, I love you. Come throw the ball with me. And then I have this like Wednesday Adam's ass angry girl who's going to say like, whatever you tell me to do, I'm not doing it. Right. You know, like there is, I'm not saying that let's blame 12 year old me for how I felt inside. You can understand it more. It's an understanding. Sure. And then, yes, my responsibility in the later years when I am an adult and I'm choosing to run an underground illegal gambling syndicate and mess around with mobsters and all this stuff.

1:18:32And like what I put them through, you know, to look at my part in that. I think being able to look at your part, no, I don't think we should blame children. Children, their brain's still developing. They didn't choose to be here. Yeah. And, you know, almost all of bad behavior comes from some sort of like pain or anger or whatever. But just starting to get into that practice of like, okay, first of all, I'm going to have courage here and I'm going to go to the places that scare me. And second of all, I'm going to take a real honest look. You know, there's all these self-help protocols, blah, blah, blah.

1:19:10But so few of them ask you to go into those shadows and to look at really like what your part might be in life. What about your personality or your behavior or your maladaptive coping strategies could be creating the same reality for you over and over and over? Right. Yeah. We talked about this last time, but, and then also realizing how the patterns of your childhood put you in the same situations over and over again. Yeah. Like your bosses, how similar they were to your dad.

1:19:51And if you want to break the cycle, usually you have to go to whatever the source of the cycle is. Conditions. Yeah. Yeah. Do you think you could have reconciled earlier or it had to come at that moment?

1:20:14I don't know. Yeah. Sometimes two people need to get to a place of, you know, call it desperation, call it, you know, the stakes are so big that you're open, that the reality changes a little bit. But, you know, maybe if we sat down, it's not that we couldn't have had the conversation. It's that, would I be ready to hear it? Would he be ready to hear it? Would we have that kind of, you know, that sort of openness? One of my favorite sections of the book is you were talking about, you had this sense of like you wanted to go live an interesting life. You wanted to do interesting things. It was actually the best writing advice I've ever gotten.

1:20:58Someone said, writers live interesting lives, right? Like people think, oh, I have to go get really good at the craft of the thing, which is important. But if you don't have anything to say or anything to draw on, what good is it going to be? So true. You certainly succeeded in the sense that you had an interesting life. That'll be hard with your kids is understanding what it did for you and then also not wanting them to do that. Totally. Totally. Absolutely. I'm still such an experienced junkie. Like I say, you know, people are like, you have to say no to all these certain things because they're not going anywhere.

1:21:39And I say yes to a lot of things out of curiosity. Sure. I think, you know, there were times where I was so regimented and every allocation of my energy or my time had to be in pursuit of either my athletic goal or my academic goal. To the point that I remember, I look at my journals and in college, I was like, I need to not make friends. Wow. Because they would take away from me. Yeah. Because it's compelling. You're 19, you know? And so like I consciously kept people at bay because they would be in the way of, and then look what happened. Yeah. I, you know, I was ready. I stepped into that rabbit hole that first night at that poker game.

1:22:29And it was like this ungoverned, uh, undisciplined, uh, so far outside of reality world. And that's, that's a big way of how it got me. Right. You know? Yeah, no, I think saying, saying yes to things is really, really important. Putting yourself in weird situations, uncomfortable situations, strange situations. This is how you discover stuff about yourself and the world. Um, and then this is ultimately what fuels whatever it is that you end up doing. Yeah. I had this really crazy experience, uh, last week. So I, you know, when, when I left the University of Colorado, I, I left, I actually couldn't finish my classes.

1:23:18I was so depressed because of skiing. Yeah. Um, and you know, like I had like a 3.9 or something and, and I was just, I couldn't stay focused. So like I dropped my classes and left and, and just felt like scared because I couldn't do it, you know? So I went to Los Angeles and I was like, Like, I'll definitely be back next year. And, you know, I'd taken the LSATs and everything. And then I never went back, ever. And then— So you didn't graduate? I didn't graduate. All right. I have six classes left. And I got hired by the chancellor to give a talk at the University of Colorado last week for, I don't know, 1 ,500 students and the Center for Leadership.

1:24:05And the chancellor was there and my family was there. and I had not stepped foot on that campus. Oh, really? Since I left. Yeah. It was such a crazy moment. How did it feel? Um, deeply emotional. Yeah? Yeah. Are they going to give you an honorary degree? They should. No, I mean, I think I probably just finished those six classes. That's cool. Yeah, you should. I should. But, you know, I just, I felt really, it was a pretty redemptive moment. Yeah, sure. And deeply emotional because for so long, I mean, I would drive, I live in Boulder, so I drive by the university. Sure. And it would just, I would have this like ache, like I'd let that girl down, you know?

1:24:54And just being back there, it was really cool. But in reality, you didn't at all. You went and learned a bunch of stuff you could have never learned in classes. and became the person you were meant to be. But sure, there is something to be said about finishing what you started. Yeah, and I think I'll probably just finish. And it's funny because I took all my high-level classes, all my specialized classes, so I think I have like Geography 101 and like Math 101 to take. I have like a year left that I've thought about going back and doing. Seems like it would take a lot of time. Yeah, I think, but you can do it all online now, can't you?

1:25:29It's true. I think I'm waiting for the honorary degree instead. I got one from CSU. You did? Uh-huh. That's cool. I gave the commencement. There you go. My dad was a professor there for 40 years. That counts. Yeah. This was awesome. Thank you. You're welcome. Thanks for having me. Of course. Yeah.

1:25:54Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, That would mean so much to us and it would really help the show. We appreciate it. And I'll see you next episode.

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From the publisher

Ryan speaks with Molly Bloom in-person at the new Daily Stoic podcast studio in the second of a two-part conversation, the first of which was conducted virtually. Today, they discuss the power of understanding and utilizing self-interest in order to connect with other people, how to improve at something every day by committing to the beginner’s mindset, what raising children can teach you about finding peace in your own mind, and more.

Molly Bloom is an entrepreneur, author, speaker, and former Olympic class skier. After her competitive skiing career was derailed by injury, Molly became a bartender at the Viper Room in Los Angeles. She eventually started an event and catering company to host high-stakes poker tournaments, which attracted wealthy people, sports figures, and Hollywood celebrities. In 2013, she was sentenced as part of a $100 million money laundering and illegal sports gambling operation and served one year of probation with a $200,000 fine, and 200 hours of community service. Her story was turned into a 2017 film written and directed by Aaron Sorkin. Molly’s speaking and entrepreneurial work focuses on inspiring and educating people on how to become top performers.

🎧 Listen to the first part of Ryan and Molly’s conversation here.

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