Kate Fagan on the Perspective Shifting Reality of Death

On today’s podcast, Ryan talks to author Kate Fagan about her new book All the Colors Came Out: A Father, a Daughter, and a Lifetime of Lessons, her reflections on the bond that she shared with her father and his difficult fight with ALS, the controversial issue of transgender athletes, and more. Kate Fagan is an Emmy-award winning journalist and the #1 New York Times bestselling author of What Made Maddy Run. She currently writes for Sports Illustrated and co-hosts the podcast Free Cookies. Kate previously spent seven years as a columnist and feature writer for espnW, ESPN.com and ESPN The Magazine. She was also a regular panelist on ESPN's Around the Horn and host of Outside the Lines. She lives in Charleston, South Carolina with her wife and their two dogs. Other books mentioned in the show: Death Be Not Proud by John GuntherStreak is a fully embedded workflow and productivity software in Gmail that lets you manage all your work right in your inbox. Sign up for Streak today at Streak.com/stoic and get 20% off your first year of their Pro Plan. KiwiCo believes in the power of kids and that small lessons today can mean big, world-changing ideas tomorrow. KiwiCo is a subscription service that delivers everything your kids will need to make, create and play. Get 30% off your first month plus FREE shipping on ANY crate line with code STOIC at kiwico.com. DECKED truck bed tool boxes and cargo van storage systems revolutionize organization with a heavy-duty in-vehicle storage system featuring slide out toolboxes. DECKED makes organizing, accessing, protecting, and securing everything you need so much easier. Get your DECKED Drawer System at Decked.com/STOIC and get free shipping. Policygenius will help you find the insurance coverage you need. You can save 50% or more by comparing quotes. And when your life insurance policy is sorted out, you’ll know that your family will be protected if anything happens. Just go to policygenius.com to get started. Ten Thousand makes the highest quality, best-fitting, and most comfortable training shorts I have ever worn. Ten Thousand is offering our listeners 15% off your purchase. go to Tenthousand.cc and enter code STOIC to receive 15% off your purchase. Sign up for the Daily Stoic email: http://DailyStoic.com/signupFollow us: Instagram, Twitter, YouTube, TikTok, and FacebookFollow Kate Fagan: Homepage, Instagram, TwitterSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:02Ryan Holiday?

  Welcome 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,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:52Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. It is already the depths of summer here in Austin, Texas. It is so hot. I'm in the middle of laying out my next book now. So on June 16th, which is my birthday, I did the edits on the final pass of my next book, which is Courage is Calling, which will come out in the fall. And then, because I'd started this book on June 16th last year, and as it happened, finished, still, and this is the key, the previous year, I thought it would make sense to start my next book. So the other office on the other side of this, my other office is covered in note cards.

• 1:35Ryan Holiday?

  I'm in the middle of laying out the book and sweating my balls off, basically, because it's so hot here. And the AC at the Pannage Porch bookstore is no good, so I'm in the middle of replacing that. It will be a cheap Thirty to forty thousand dollars to get new ACs in here. So I'm trying to just grit my teeth and bear it for now. Although, since I have employees and customers, my ability to suffer through things is not my burden alone to bear. And I have to provide these people with an AC, or there will be an insurrection, almost certainly. But I did have a small window unit running.

• 2:17Ryan Holiday?

  You may have heard it, you may hear it right now, but you may have heard it during my interview with one of my favorite writers, one of the few people who's now been on the Daily Stoic podcast twice. I had her on, I guess, last year to talk about a book called What Made Maddy Run? Which is about the tragic suicide of one of the world's best cross-country runners, and why that would happen to such a talented young woman. It's one of my favorite books. It's a book I've recommended to all the sports coaches that I know, recommended to parents. Actually, just the other day, a customer came into the painted porch. I saw them looking at the sports section. I saw them pick up What Made Maddy Run? And I said, "You've got to read that book. It's amazing."

• 3:02Ryan Holiday?

  And she took it home with her, because it was amazing. What Made Maddy Run is also, as it happens, inspired by the title of one of my favorite novels of all time, What Makes Sammy Run. I think one of the great novels of all time. But anyways, today, I'm talking to Kate Fagan, who has a new book out called All the Colors Came Out: A Father, a Daughter, and a Lifetime of Lessons. It's a book about her father, a D1 collegiate basketball player, who ends up getting ALS. And she leaves her job at ESPN, partly to take care of him. And what does she learn about life, about death, about happiness, about struggle? As she watches the person she loves more than just about anything in the world succumb

• 3:47Ryan Holiday?

  to a horrible, merciless disease that, towards the end...

• 3:53Ryan Holiday?

  Takes away even his ability to communicate. And, and we talk a lot about those last 48 hours that they spent together and, and what she learned and what you can learn. It's absolutely a beautiful book. I was glad to blurb it. I don't blurb really any books. In fact, I have a rule against blurbing books because I don't have the time. I don't want to hurt people's feelings. I just have a, a general rule against doing it. But this was one I, I did blurb. I said, once again, in a story of pain and loss, Kate Fagan manages to find beauty and humanity to write a book that teaches us a great deal about our own lives. Anyways, I think that about captures it, but you, you've got to listen to this interview.

• 4:37Ryan Holiday?

  We ended up going even longer than an hour because we really got into it. So I appreciate her giving me the extra time. Kate Fagan is a number one New York Times bestselling author. She was a seven-year columnist and feature writer at ESPN and ESPN, the magazine. She's regularly on ESPN's Around the Horn and Outside the Lines. She spent three seasons covering the 76ers for the Philadelphia Inquirer and she lives in Charleston, South Carolina with her wife and their two dogs. You can follow her on Instagram, at Kate Fagan three. You can follow her on Twitter, the same thing, at Kate Fagan three. And check out What Made Maddy Run, beautiful haunting book.

• 5:20Ryan Holiday?

  And check out All the Colors Came Out, a book that will break your heart, but also inspire you. It's an important book as, as we talked about in the interview, I think a timeless book. I also recommend another book that I love in this interview called Death Be Not Proud by John Gunther. You can get those books in the show notes. You can get Kate's books in the show notes on your podcast app. Pick them up at The Painted Porch, which is my bookstore, either in person or online at thepaintedporch.com. I appreciate the support. Support indie bookstores if you can, or just get it wherever it's cheaper if, if you weren't going to get it otherwise. Here's my interview.

• 5:59Ryan Holiday?

  Well, it's awesome to talk to you again. I'm sorry that we're talking over another book inspired by a heartbreaking tragedy.

• 6:08Speaker 01

  It seems to be my specialty, I think.

• 6:12Ryan Holiday?

  This one's a little closer to home. I'm very sorry about your loss.

• 6:17Speaker 01

  Oh, thanks, Troy.

• 6:19Ryan Holiday?

  It must have been very difficult to write. I mean, obviously, talking about Maddie in the first book, it's sad, but it's not your family. It must be something different, right?

• 6:30Speaker 01

  Yeah. Well, the overlap between how I felt writing Maddie and how I felt writing this, there's a lot of similarities because people would ask me about Madison Holleran's story, the student athlete who died by suicide and working with her family. Well, that must have been a dark place to live in. And my reality was that writing about people's humanity made me feel closer to my own and to theirs.

• 6:57Ryan Holiday?

  Sure.

• 6:59Speaker 01

  And I think similarly, writing about my dad and his death and ALS, similarly, both experiencing his death and writing about it made me feel closer to my own humanity. And so it actually wasn't, it wasn't a dark place to live in. It wasn't a dark place to be. It was, and I'm lucky for this, but it was very beautiful in many ways.

• 7:27Ryan Holiday?

  Yeah, I think, I think people think that writers sort of have it all in their head and you're just like, you're putting down this sort of ironically authorial sort of view of the universe, but you're usually sort of figuring out what you think as you write. That's what, that's what writing is. So I imagine getting to spend all this time with your dad, both when he was alive and then after he died, through sort of trying to figure out what he meant and what was important to you was also, that's what, that's what the beautiful part was, was really figuring out what your dad meant to you, not in just an emotional place, but in a place where you had to articulate it on the page to a stranger.

• 8:09Speaker 01

  Yeah, and I had, I loved my dad and I was close with him, but I'd never thought this much about my dad.

• 8:15Ryan Holiday?

  Right.

• 8:16Speaker 01

  As in the year of writing this book. In fact, since the book came out, I'd say it's been the hardest time for me because I was with him and even though he was sick and there were many incredibly difficult parts of that illness and his death, and then I'm writing the book and I'm basically reliving our life together in writing the book. And so there wasn't, it wasn't like the on, I kind of almost put a dam up from the onslaught of grief. Not that it's been an onslaught, but I got to live with him again. And even in, like you say, I mean, the book, in the, in the book, I'm peppering all of these life lessons that, that I learned on the basketball court.

• 8:56Speaker 01

  And if you're reading it, you could think that in the moment my dad mentioned something or taught me something that I had this very wide lens view of what it meant.

• 9:09Ryan Holiday?

  Yeah.

• 9:10Speaker 01

  But a lot of those lessons only exist because of long walks I took after his death and thinking through how those lessons actually have applied to my life or how they could apply to people's lives. And so you're completely right in that it was the thinking in that year of writing the book that maybe really expand what my dad meant to me and, and the things he said and did and try and make them into a big picture kind of philosophy.

• 9:35Ryan Holiday?

  And I feel like as an athlete, and I found this with the athletes that I've talked to, they kind of have, they have this knowledge, but it's often like in their body. So it's not like in their minds that they can't articulate it. And it's only with reflection that it comes out. I, I remember I was reading about, uh, Jack Harbaugh, so John Harbaugh's father. And there was something that he would repeat like every day when they would, he would drive him to school and he's like, we're going to attack the day. And it was something, some like cheesy dad thing, you know? And, uh, he, the, the kids hated it. They always grown their eye, rolled their eyes and groaned. And then it was like 30, 40 years later, one of them gets a job and he's doing a press conference, like announcing the job and he repeats like this thing.

• 10:19Ryan Holiday?

  That his dad had said that he had never repeated ever before. He'd never acknowledged in any way. And that's when the dad, it hits Jack Harbaugh like, oh, my God, they were actually listening. And they were listening, but it was at like a different level. And it took 40 years for it to like bubble up and be sort of repeated for the first time. And so I got to imagine there was a lot of the stuff your dad told you when you're on the basketball court, when you're driving, whatever. You absorbed it, but you didn't actually process it until like now.

• 10:53Speaker 01

  Yeah, OK, and that's, that's really interesting, too, because as someone whose background is the beat, I was a beat writer for the 76ers for three years. And so the hardest part of that job was attempting to get athletes to explain in an interesting way, the movements that they make that are ingrained in them on the basketball court. And it was almost impossible to do that, to get them to have any sort of perspective on why they do what they do or how they do what they do, or what it means in the larger sense. Because that's not, that's not part of what being an NBA athlete is until, like you said, you sit down and, or your, your job, like my job as a beat writer,

• 11:37Speaker 01

  was to make sense of the movements that they make. And there, I never thought about this before you asking that question, but there was a direct parallel between watching NBA players struggle to articulate why they do what they do and spending a year trying to look back at the very athlete like mentality that my dad had and extract a larger meaning from it. Because there were many things that he said, like, for example, you know, he taught me about the, the little notch in the middle of every free throw line in the world. You'll find this little indentation that completely marks the centerpiece, center of the line and of the rim.

• 12:18Speaker 01

  And my dad did not mean this as a kind of zen philosophical point of view about the world, but I certainly started to live it that way. But it took me the three weeks of writing that chapter to actually articulate what that feeling was and what those movements actually meant in a larger sense.

• 12:36Ryan Holiday?

  No, that's beautiful. And I do think athletes have, there's that idea of there's different kinds of intelligences. I think there's like supposedly seven kinds of intelligences, right? Four, I forget what it is. But the idea, when you talk to, like, I found this when I've talked to athletes, and then I've talked to, like, hip-hop artists, to demographics that I would say historically were deprived or screwed over by the education system, right? So they often will lack what you and I have, which is a lifetime of practicing explaining exactly what we mean and articulating it. That doesn't mean they don't have the exact

• 13:17Ryan Holiday?

  same observations about reality, and they're not seeing everything that's happening. They may actually be experiencing a lot more. It's just, they don't have the practice of communicating about it. So you have to, you have to, you have to find a way to get at that. And it's often beautiful and done through sort of unexpected analogies, like you just said, because they're not, they're not dealing even with the same point of reference of reality. So they find a way to communicate it, like, yeah, find the notch in the free throw line. That's like, that is a Zen observation.

• 13:50Speaker 01

  Yeah, it is. It's completely a Zen observation, like so many of the things that my dad said. But to the point you're making, I think you're right in that, having, you know, grown up, maybe being forced to write essays, that the point of it was for me to, like, analyze some situation in a meadow way. And that start to be, that cultivated in me an idea that that's how I saw the world. And maybe some of that was a class issue, and some of that was just the way different intelligences work. But what was really interesting to me, even in writing this book, was even the process of writing it and the way my brain works, was so clearly different than the way my dad's brain worked.

• 14:33Ryan Holiday?

  Yeah.

• 14:33Speaker 01

  And all, like, these basketball lessons that I take to mean so much more, I would be shocked if my dad meant them as more. Like,

• 14:42Ryan Holiday?

  Sure, sure.

• 14:44Speaker 01

  He obviously just meant, make your last dribble the hardest, because it's better going up into your shot with momentum. And I'm the one trying to, like, extract some large meaning from it. And it is a very different, it was very different getting, trying to get into my dad's brain, because it worked so much different than mine did.

• 15:05Ryan Holiday?

  Well, and yeah, I don't want to be condescending about it. It may actually be a much better way to live. Like, you know, you'll talk to an athlete and they'll be like, you know, I just went out there and did my best and you gotta, you know, thank God or something. You know, they'll like sort of repeat these like cliches, like the sports cliches. And like for a writer, you're like, oh, you can't do that. That's a cliche, but they actually mean it. Like that, they're, they're actually operating on a level often of presence and earnestness that, that like as a writer or as a, as a literature sort of based worldview that you're like, you're not allowing yourself to operate. Like I loved your dad's mantra when he gets out of bed in the morning.

• 15:48Ryan Holiday?

  Like I would, I would never allow myself to say that out loud. I would feel too awkward, but like, it's probably a much more joyful way to, to, to, to attack the day.

• 15:59Speaker 01

  Yeah. Well, so one of my, the favorite interviews I ever did when I was at ESPN was with Abby Wambach. And we were talking about the header on the cross from Megan Rapinoe at the 2011 World Cup against Brazil. It's like this famous sports moment that kept the US from being eliminated in the quarterfinals, which would have been their earliest exit ever in a World Cup. And now in particular, the US women's national team, they know that if they advance far in a World Cup, I mean, that's millions of dollars per, per player. In a way that you, a different soccer team at the world stage, like they still have their premier league team, you know?

• 16:40Speaker 01

  So, and I say this to say that the pressures in that moment are extreme for a female player because of what it might mean long-term. And in talking to Abby, I'm like, well, you must've been thinking all of this, right? You're, you're at the World Cup, you're on, you're on the field and you're thinking it's the 111th minute and if we don't. You know, equalize, get an equalizer, like your, your whole longevity and your whole ability to make it. Right. So I'm taking her through a meta-awareness of that moment.

• 17:12Ryan Holiday?

  Yeah.

• 17:13Speaker 01

  And she's like, oh, my God, no, I've never thought any of those things. I was thinking about, she's like, I was just alive and the grass was green and I was just thinking I had to, and I'm like, wait, you never thought to yourself, what are people thinking as they're watching me? And she's like, I could never do that. How could I ever succeed if I did that? And I was like, well, that is why I would have failed in that position because I am constantly analyzing how the outside view of what I'm doing will be seen.

• 17:46Ryan Holiday?

  Yeah, like the, I just went out there and did my job, or it was so beautiful to just like play as a team, you know, like, I think you may actually have to operate at that level because the, perhaps it's impossible to be physically and mentally at equal levels of awareness. And maybe you have to tune up one or tune down another to operate at that level.

• 18:09Speaker 01

  I think that's exactly what Abby was, again, an athlete who would not have been able to articulate it like that. And not to say that, I mean, I think Abby Wambach is brilliant in ways that are completely, you know, tangential to ways other people are brilliant. But you're exactly right. And that what she was getting at was that to be perfectly physically in tune and aware to what my body needed to do in that moment, I could not take any energy to consider the TV audience on ESPN and what they might be thinking about the US team, or what endorsements I might not get if we lost that game. So it's like completely tuning down the meta-awareness and completely tuning up like the in-body experience.

• 18:53Speaker 01

  And that is not something that, I don't even know that she's, she's probably doing it with practice, or it's more of her natural state, but it didn't seem like something she was controlling. It was like a default state that she'd gotten herself to.

• 19:07Ryan Holiday?

  Yeah, like I was talking to Steven Pressfield, who wrote The War of Art, and he talks about like the muses. And I'm like, you can't possibly believe that your artistic stuff is coming from the muses. And then on the other hand, it's like, that's probably a decent coping mechanism to not overthink where the hell all this stuff comes from. Like, again, when you, when you hear an athlete thank God, or, you know, thank something other than themselves, it may be part of the same thing, which is like, you can't be too self-conscious of what you're doing, or you won't be able to do it as well as if you are just in a flow state, connected with who you are and what you're supposed to be doing in that moment.

• 19:47Speaker 01

  Yeah, and I think the flow state gets you to a place where you realize that you're not fully in control of every thought and every good idea that comes in your mind. Like, they're coming from somewhere. And it's easier to kind of, to say something like them. And I do actually ascribe to this idea of like, not muses in the way that our culture, you know, suggests them, but muses in the way that I can't conjure them, therefore I'm not fully in control if they don't show up either.

• 20:20Ryan Holiday?

  Right, right. And, and to think that you're fully in control, and that this is all you, is probably actually an unhealthy way to do it, and puts too much pressure on yourself. So it's, it's a way of like, not staring directly at the sun.

• 20:34Speaker 01

  Yep, exactly.

• 20:36Ryan Holiday?

  So, so you're also an athlete, though. So where does this come from in you, where you have the ability to do both, where it seems like your father was sort of fully identified as an athlete his whole life?

• 20:49Speaker 01

  Well, I think, I don't know if this is why, but my dad seemed to have been born to be an athlete, in that he loved it, and it was the thing that made him, that, that made him feel complete. Like, he played basketball up until and through his ALS diagnosis, until he physically couldn't do it anymore. And I never felt that way about sports. And I never thought sports were like, my, my full passion. I didn't feel fully alive when I did sports. Like, because I think that- I think that when I talk to somebody like Abby Wambach, not like she's obsessed with soccer

• 21:32Speaker 01

  and she loves it forever, but that sometimes when she plays it, she can forget who she is and she can go into that state where you lose time. I never really was able to achieve that in basketball. I am able to achieve it in writing. And so I think that's where my dad was able to achieve that in basketball and I was not that person.

• 21:54Ryan Holiday?

  Got a quick message from one of our sponsors here and then we'll get right back to the show. Stay tuned.

• 22:01Ryan Holiday?

  Can you be great at sports or anything without that thing? Do you think is that like, because you were good and you made it to a certain level, but not the Abby Wambach level of basketball? Do you think that that was just, just, you know, just like some people are born two inches too short? Do you think that's what it was for you?

• 22:22Speaker 01

  I think that the main, I don't think I ever could have been great, like WNBA All-Star great. But I do think I could have played at the professional level if I hadn't had that attribute. If I was more, if I could lose time playing and I was passionate about it, I think I would have been better. I think that when we talk about the all time greats of things, this is, this is me thinking on the fly here, not something I've like studied. But I think when we talk about the all time greats, they probably have the perfect mix of all of those things.

• 22:59Ryan Holiday?

  Yeah.

• 23:00Speaker 01

  I don't think that you can be an all time great and not think that that sport is somehow your passion, whatever that means. Not that you're not going to fall out of love with it or have times when you don't want to be doing it. Those things will still exist. But I think that you are able to lose time when you play it. I think to be an all time great, that needs to be true for you more often than not.

• 23:23Ryan Holiday?

  Yes. Yeah. Like when I talk to people who are thinking about doing books, and I'm sure you have ideas or you see things that could be good books all the time, but you can really only write, I say you can only write the ones you can't not write.

• 23:36Speaker 01

  Yeah.

• 23:36Ryan Holiday?

  So like it has to be something that it would be physically painful not to do. That's the only way you're going to get something great, like. You had to write this book, right? Or there was something about Maddie's story that like you had to solve by writing about it. And then all the other books that you haven't written fall in the other category.

• 23:58Speaker 01

  Yeah. Or I think there are people who write books and they just write them because like that's convenient for them then. And I don't think, again, if we're, if we're making the comparison to like what separates the all time greats like a Kobe or an MJ, I think it's, you can't not do this thing versus I'm doing this thing because it's convenient. Cause I think there's plenty of books that exist because, all right, well, I have to do something this year and this was a good idea and I'm writing it. But I think there's a difference, like this book for me, All the Colors Came Out is not that. It's not, well, I had this year free and I guess I'm, I guess I write books, so I guess I'll write this idea.

• 24:37Speaker 01

  No, this was like, this was my collision of both love and dedication and voice and momentum and motivation. It was like a collision of all of those things.

• 24:52Ryan Holiday?

  Well, I think that makes for the best stuff and weirdly the, the, the stuff that allows you to sleep at night because obviously you want this book to be successful, but to a certain extent, because of what you just said, that it exists is the first victory or, or is a form of success that's totally up to you and totally on you that really no one else could have prevented. Like you wanted to write the book, you, Rick Rubin just tweeted something about this, that the day your thing comes out, like you've already succeeded. And I think that's true. The only caveat I would put on it is like, unless you didn't do your best. Like if you had to write this book and then because you were distracted or you were afraid

• 25:36Ryan Holiday?

  of being vulnerable, you only gave it like half of what you knew or you held something back, then it could be a failure, I suppose. But I think when you do something that you can't not do. By nature of doing it, you've won, unlike sports, which like the box score at the end determines who won or lost.

• 25:55Speaker 01

  Yeah, and, and writing this book for me was, I guess my through line of this conversation with you is Abby Wambach. But it was my Abby Wambach header against Brazil moment because it was really the first thing I'd ever worked on, that while writing it, I was fully present and joyful at the writing of it. Whereas other things I'd written, I spent a lot of time Googling bestseller lists, wondering if I'd make them, or like, you know, when you're writing your first book, you're spending most of your time like looking at agent message boards or something, or you just spend more

• 26:37Speaker 01

  time wondering what the product of your creation will get you, rather than really living in the writing of it. And this was the first book I'd written where I was fully satisfied at the end of every day, just taking a walk in my neighborhood after having written whatever words I was gonna write, and actually saying out loud, oh, the process of writing is the victory. And the process of writing this story is the victory. And that was my very much, I'm on the field and I'm taking joy in the moment and I'm not worried about the, the outcome or the validation that comes on the backside of it. That, that always comes later, that always comes later. Once you, once you publish, you can't help but worry about that, but.

• 27:18Ryan Holiday?

  But there is something to be said also, I think, for having, having had done, done those things. So, you know, Maddie was a number one New York Times bestseller. So, there, there is also something where you can feel a little bit satisfied having crossed those things off the list. And then you can go like, okay, I've arrived, I don't really have to prove anything. And I think that actually generates better work because like, as you said, you spent in, we all spent a not inconsiderable amount of energy focusing on those external things, which is. By definition, energy you're not spending like in the flow state making the thing you should be doing. So there's a cost to it, to the wandering eye.

• 28:01Speaker 01

  Oh, yeah, in the same way that there, you know, the thing I'm sure you've you've talked about a lot is like, there's a cost to checking your email while you're on the phone call with somebody. And I can see that, I can feel that cost when I come back to a conversation that I'm having while I'm checking my email. And I have, I don't even know what the cost is, but it's probably, you know, tenfold. If you're writing a book, but you spend 30 minutes Googling the bestseller lists. Like, that's a, that is a cost on it. But one, one thing I've, one, one reason why I think this book in particular

• 28:44Speaker 01

  feels different to me than other books is that like I, it's not, and this is going to be counterintuitive. Like, it's not timely in any way. It's not, it's not built around a cultural phenomenon that is particular to 2021. It's because a lot of books are created that way. Like, what, what will people care about in 2021? Are they going to care about these three topics? And I guess I'll build a book around it. I mean, this book, you know, is, it's tough to get people to pick it up because it's, there's no reason to talk about it on June 24th versus any other day of the year. And it's really sad, or people think it's sad based on the topic.

• 29:26Speaker 01

  And I don't think people gravitate toward wanting to deal with that, especially after a pandemic. So I feel like, anyway, I feel like all those reasons make it obvious it was the right book to write for me because there was no other motivation than writing it.

• 29:44Ryan Holiday?

  Yeah, there, and I've experienced that with some of my books where the downside is, yes, there's no news hook or news peg, as they call it, so it's not timely. But the upside is that it's timeless, right? So, so you, on the one hand, you don't have as favorable conditions. And yet, over a long enough time, you actually get sort of more, I don't know, at bats. Or you have, you have a longer runway. I'm getting ridiculous with the analogy, but it's, it's better because it, most books have an expiration date. And And then when you write something that connects to something that goes to what makes

• 30:27Ryan Holiday?

  us human, it could be relevant 50 years from now or 100 years from now. There's a beautiful book called, I'm now forgetting the name, but John Gunther, who was like one of the great journalists of the 20th century, like the 30s, 40s, 50s, he wrote this book about about his son, I want to, I want to find the name, whose son was dying of cancer or something, his younger son, and he wrote this beautiful book about it. And it's like, I'd never heard of John Gunther. I'd never heard of his son. It was no longer a news story. And you read this sort of heartbreaking book, a sort of a letter from a father to a son about trying to capture this, this boy's life, this brief life, you

• 31:09Ryan Holiday?

  know, the upside is that it's completely timeless and it, it's, it's impacting people far after both of them are gone.

• 31:19Speaker 01

  Yeah. And I think about that a lot, even in terms of the, my first book, What Made Maddy Run, even though I think it has a long shelf life, it's not timeless because it's about-

• 31:35Ryan Holiday?

  It's about social media. It's about a specific time and place. And yeah.

• 31:39Speaker 01

  Yeah. I mean, I think that it's not like it's like a three month window of accessibility for people, but I don't think in, unless as a historical artifact in 2070, are people going to be picking it up, except to think, oh, wow, that's what they, that's how they responded when social media first came out. And I think about that a lot in terms of all the colors came out in that there's nothing about it that pegs it to 2021. It is very much just a human story that I think would be, will be relevant whenever. And at least there's, there's hope on my end when it comes to the universality of the story I'm trying to tell.

• 32:20Ryan Holiday?

  Yeah, so I found this book. It's called Death Be Not Proud. It was written in 1949. I pulled up the Wikipedia page. Listen to this sentence. This sentence is incredible. So it says, "Soon after the book's release, Dorothy Thompson, who's apparently a, oh, she's the first American journalist expelled from Nazi Germany in 1934." Anyway, she says, "Had his son lived to be 90 and had his achievements filled encyclopedias, he could have made no greater achievement than this transmitted by his father to show us what, on its highest levels of courage, serenity, truth, and beauty, a human life can be, to show us that as we live, we die, and that life and death are one." Oh, man, that's amazing.

• 33:01Speaker 01

  I mean, other than the title, that's essentially what my book is about. But other than its title, which might date it to 1949, other than that, that is exactly, that is the timelessness that I think All the Colors came out has. And I don't mean that in like a egotistical way. It's just by nature of the story being about the decisions we make around death and when loved ones die, and the honest conversations that hopefully we're having, and the honest, and the thoughts we have that sometimes seem unsavory to us but are universal. I mean, all of that, to me, is a universal story. It just happens

• 33:42Speaker 01

  to be about a father and a daughter who grew up loving the 90s Knicks. You know, that's the specifics of the universality.

• 33:50Ryan Holiday?

  Well, so one of the things that was kind of timely about your book that I wanted to talk to you about, I was reading, I think, a piece in The Economist, and it was saying something like, "One out of every five families is estranged," like a son or daughter is estranged from their parents, or vice versa. And they didn't really explain why this was, but it was striking because your book kind of talks, it's not that your father, you and your father were estranged, but as you got older, you kind of drifted apart. You weren't as close as you were at the end of the book. I mean, obviously, that's one sort of message of the book, is to sort of be with people while you can be with them. But I was just curious, what do you think when you hear that statistic?

• 34:32Speaker 01

  Well, what comes to mind for me is that

• 34:37Speaker 01

  I I I I'm surprised that that number is so high, actually, although it's not like I've read a lot of data on estrangement. But what what comes to mind for me is the fact that the estrangement that my dad and I had, I think is more common. And that is that we still talked all the time. We just avoided anything important or deeply meaningful. And so when I talk about the relationship with him, it's not, it's not a physical estrangement. It's an emotional estrangement.

• 35:12Ryan Holiday?

  Right.

• 35:13Speaker 01

  Because he he would call me twice a day. He'd always call me when he got in the car on his way to work and we got in the car on his way home from work, at a minimum, two times a day. So, I mean, this guy liked to be in touch. So there's, there's no part of our relationship where I'm, where it meets the, the technical definition of estrangement, except for the fact that when you look at the childhood we had up until I left from college, there was so much more of a, of a closeness, an emotional closeness, a willingness to be vulnerable with each other. And I think the story I'm trying to tell is one that so many people can relate to and that it's one of those relationships in life where you've known for a long time that something's

• 35:54Speaker 01

  missing and that there's something that has happened, maybe you've said or done something that you want to reconcile and apologize and get to a better place with this person, but you, you're not quite sure if the thing you feel is real.

• 36:10Ryan Holiday?

  Yeah.

• 36:10Speaker 01

  Or if it's a figment of your imagination, or if they feel it too. So it's like, it's a very nuanced kind of estrangement, if we're going to use that word. And I think it's much more common that people experience it this way, rather than we haven't talked in 10 years. Although one in five is, is actually a lot.

• 36:29Ryan Holiday?

  Got a quick message from one of our sponsors here and then we'll get right back to the show. Stay tuned.

• 36:36Ryan Holiday?

  Yeah, I think it's partly a boomer thing, too. I saw a meme the other day that was something, the effect of it was like, your parents are telling you something like, you know, the neighbor three doors down just put in new flower, like, you know, the neighbor three doors down's cousin just put in new flowers in their garden. And then it's like, you also find out, like, a month after it happened, that your mom fell down the stairs, broke her arm, and it's now has like 15 pins in it. You know, like, like this sort of weird sharing and, and focus on things that do not matter at all, at the expense of even the most basic personal information, or to say, to say nothing of emotions, or vulnerabilities,

• 37:21Ryan Holiday?

  or fears, or worries.

• 37:23Speaker 01

  Yeah, to not even get that deep as that. These are just like exchanging, just, and I, and I didn't, maybe it is a, it is a boomer thing that you're talking about, this idea of, of just like arcane details that are happening in the neighborhood and being, and being shared. But the, the thing that I've come to realize going through this with my dad, because I still have people in my life who are engaging with their parents in the way that, that you talked about. And it seems to me that that behavior is motivated by sparing people?

• 37:58Ryan Holiday?

  Yeah.

• 37:58Speaker 01

  Or not being a burden on a loved one or, or a kid. And the one thing that I will always be grateful to my dad for, among a lot of things that I'm grateful to him for, was that he didn't come to this disease, to ALS and the process of it, believing that I had to be separated from it to either spare me or spare him. He was very, he was very much from the beginning, and this is... This surprised me because he seemed to, he seemed like he couldn't be vulnerable about things, but when it came to the physicality of the disease and the emotion that the disease

• 38:42Speaker 01

  brought, he very much wanted me to be a part of it. And I, I will be grateful for that because I think that when people, when people separate their loved ones from what they're going through, they're actually keeping their loved ones from what can be a very a positive emotional experience to be present for someone going through something like this.

• 39:07Ryan Holiday?

  Yeah, there's that expression, you're only as sick as your secrets. And I think a lot of people are very sick and they keep secrets about things that not only like are not shameful, but like would be very helpful to everyone involved with that we would share, you know, like, like finding out, oh, hey, there's this rampant history of drug addiction or mental illness in our family that by not sharing, you make the kid face this thing totally alone and think that they're the problem, right? Like, I, I, I think this is also, I think one of the messages of, of what makes Maddy run is like on both, both

• 39:48Ryan Holiday?

  sides, like parents pretend everything is fine. And then when the kid really struggles with something, they have no support network, no frame of reference to be able to share what, what to, to, to be able to notice that something's wrong. And then conversely, when something's wrong, they don't feel safe or good sharing it because they don't know how it's going to be received. You have to create like habitually over the course of a life, space where this stuff can get talked about because the one time you don't talk about it, that's, that's, that's the thing that changes everything.

• 40:24Speaker 01

  Yeah, well, that's an, that is a through line between those two books that I hadn't even connected, being that what made Maddy run and Maddie's family not communicating openly about mental health issues that were running in her family, which, Ryan, like you said, leads her to go to college. And when she starts to battle her own depression, she thinks, what is this thing? I have no idea what this is. I have not, to me, it feels like, you know, Maddie saying to herself, this must be something that's going to go on forever. Because I have no frame of reference to say, well, I know people in my life have gone through it and gotten to the other side. And then on top of that, feeling like the problem is her, rather than, actually, this is something that we, that runs in the family

• 41:09Speaker 01

  we could talk about. And so I think that idea of like, but that takes vulnerability. And, and similarly, I think, when it came to my dad, it took vulnerability to be able to say, I'm so sick. And how sick, not that he could have hidden, I mean, you can't hide ALS, but you can, but you can shut yourself away. And a lot of people do do that because the disease makes you, you know, physically and emotionally at times, someone that you don't recognize. You don't recognize yourself in the disease. But, so the idea that he could be vulnerable enough to say, I'm going to let you in and see me when I don't even

• 41:49Speaker 01

  like who I am, that took a level of vulnerability. And they're different vulnerabilities. But if you don't, if you're not open to them, right, not open to speaking about things that run in the family, or not open to this idea of letting your kids in. And again, I don't, that's not to say every caretaking, every, every child whose caretaking is always a beautiful experience, because it's not.

• 42:11Ryan Holiday?

  Yeah.

• 42:11Speaker 01

  But I think being, being open to expressing the vulnerability that he had was a gift to me, that he was willing to do that.

• 42:19Ryan Holiday?

  Well, and this is why I like Brene Brown's work because you keep saying as vulnerability, the other way to define that would be it was immensely courageous, right? Like, it takes, we think of courage or strength as the ability to just sort of grit your teeth and bear it, to sort of, to suffer silently, to put on a brave face for everyone. But actually, the courageous thing for your father was to let you in, to be, to allow himself to be seen as something other than the person he'd wanted to be his whole life or worked his way to be. And, and, and the reason this is so important is that it's a, it's an incredible gift

• 43:01Ryan Holiday?

  to you and the people around him who, in the future, will suffer and go through things and need help or need to be vulnerable. And you have an example of someone having done that.

• 43:14Speaker 01

  Yeah. And on a very like, you know, on a very, almost like quid pro quo level, it's like, I was there for him. And so then, when I'm sick, I won't think, well, I should just shut myself away.

• 43:27Ryan Holiday?

  Yes.

• 43:28Speaker 01

  Because that's the model that has been shown to me is that you should, you shouldn't ask for help from your loved ones. It's almost like I've paid into it now.

• 43:36Ryan Holiday?

  Mm-hmm.

• 43:37Speaker 01

  Both the emotion of it and the physical nature of it, I've, I've paid into it. And I, and I know now, as I get older, like, there are things I learned that I wanna, ways I, I wanna behave when I get sick, that he very much either showed me or taught me or opened the door to me feeling. And the interesting thing about courage in all, in this was like, his, his decision to let us be a part of it, even though he didn't feel like who he was, like the big, strong, tall dad anymore, that was one level of courage. And then the next level of courage was...

• 44:14Speaker 01

  Him being willing to surrender to death. Because there was a period of time in which he wasn't. And he thought he was being courageous by continuing the fight. And, you know, no weakness, no surrender, all of that belief system. And the rest of us in his life didn't see him continuing the fight against ALS as a courageous thing. We started to shift and be like, actually, the most courageous thing right now is to realize the impact on your family, the impact on the collateral damage all around you, and the winless battle, and bow out gracefully, to use all of my sports cliches.

• 44:58Speaker 01

  And that was kind of the final step of courage. We don't always have to battle until the bitter end. That doesn't always have to be the way.

• 45:06Ryan Holiday?

  Well, and final step, it's sort of the ultimate thing, right? Going back to Cicero, Cicero says that to philosophize is to learn how to die. That that's what we're all doing. We're all, over the course of a life, learning how to do the one thing that we all have to do, the one thing that all humans have shared for all time. And yeah, it seems like, in a sense, by allowing you in, and the real gift that your father gave you all, and then gives the readers by opening up to a writer, is that he allowed you to experience and struggle with the struggle that we all have, which is being afraid to die.

• 45:47Speaker 01

  Yes. I mean, that's the through line of the book, well, in part being like life lessons that were taught through the game, and then life lessons in that last year of his life, as he's in the final year with ALS. I'm trying to show a portrait of an athlete, which is a different mentality than other mentalities. It's very much a portrait of an athlete, like you said. Working through the mindset of who he wants to be and how he's going to, one, accept death and then approach death. And for much of the book and the story, he is unwilling to do so.

• 46:28Speaker 01

  Because he just, he sees it, one, as, I think he sees it as failure to some degree, that he's giving up.

• 46:35Ryan Holiday?

  Yeah.

• 46:35Speaker 01

  And then, and then of course, it's just, it's losing. It's definitely in his mind for much of the book, losing. And then there's just fear on a very primal base instinct of fear.

• 46:47Ryan Holiday?

  Sure.

• 46:47Speaker 01

  And it's not until the very, very end that he starts to realize that surrender is what he needs to do. But the complicated thing about, you know, the book is that by the time he realizes this, he has completely lost his voice. So there's, there's this section of time where I, I'm, I'm very, I'm almost desperate to know what it's like for him. Because aren't we all just so curious of?

• 47:15Ryan Holiday?

  Sure.

• 47:15Speaker 01

  When someone is finally looking at death and, and has come to philosophize to the point that they are accepting that death is going to happen, I want to know why and how and what that feels like. But he couldn't talk anymore. And so was trying to piece together small things that he was doing and ways in which he was communicating by blinking and trying to, in my own mind, as the writer of this story, piece together what he must be feeling and thinking and what it all means.

• 47:49Ryan Holiday?

  What do you learn from like how he lays there and how he holds his head up and, and yeah, uses his eyes? What, what, what do you feel like he communicated with you about the hardest thing that we all have to do?

• 48:05Speaker 01

  I think what was, what was most compelling to me was that the, so, the, the very unique way in which he died was that we decided to take him off his, his ventilator, his tracheostomy. So, but we had about 48 to 72 hours before the hospital was willing to transfer us and make this happen and have all the paperwork done. So it was almost like. I mean, in a way, he's almost like a death row, right? He knows, he knows when this is going to happen, but we can't do it yet. So he has this chunk of time. And it was really interesting to me, the things he was bringing up.

• 48:48Speaker 01

  Because even though he couldn't talk, he could, he could mouth something and we could try to read his lips. Or we had a system where he could, you know, left eye was yes, right eye was no. And the night before we transferred him to the ICU to start the morphine drip, which would end his life, he was really, he was really forceful about translating this one sentence. And when I finally got it translated, he, the sentence was, "The, the fight outside CVS." And it was this fight that my dad and I had had 15 years prior in Rhode Island.

• 49:30Speaker 01

  And it was the biggest fight we'd ever had outside of a CVS. And it was about a stupid thing, doesn't matter now, but like, we'd really gotten into it. And it was really compelling to me to, to see that the point that he brought this up, the second I said, "The fight outside CVS?", you know, he blinks his eye, "Yes, yes, yes." And then he mouthed, "I'm so sorry." And it just, I was like, we all think that at the end of life, we're going to be like reminiscing about the weddings and the vacations and, and deaths of other people. But like, that was something that had given our relationship like texture.

• 50:14Speaker 01

  It was this thing. And, and that's what he was thinking about in these final hours, was like moments in his life that he, maybe he hadn't communicated properly and he wanted to go back and just make sure I knew, as I kept forward in life, that I knew that he too wanted more from our relationship and that he too had made mistakes. Um, and so it was very compelling to me. Not that it's not common sense that we want to reconcile all of these things, but that very specific thing we'd never talked about since the day it had happened, until the day before he died.

• 50:54Ryan Holiday?

  Well, and obviously, I didn't know your father, so this might not be what he was trying to say. But I think the other part of that is, you know, we think, and we say this, like, when you were thinking about leaving ESPN, you know, we go like, am I going to regret doing this or not chasing my passion? Am I going to regret not going to this opportunity to do X, Y, and Z? We think we're going to regret things that have to do with like pleasures that we didn't take, or roads that we didn't take, or things that we didn't do. But in reality, you know, I think what we end up regretting is the times we lost our temper about things that didn't matter, that we regret the way we treated people that we cared about, and the way

• 51:38Ryan Holiday?

  we treated them wasn't a reflection of what we actually felt about him. So I wonder if what your dad was, your dad didn't want that thing, which is so meaningless in retrospect, to mean anything years later. You know, like, he didn't want, he didn't want that to go unaddressed because it didn't matter. But at the same time, it mattered so much.

• 52:04Speaker 01

  Yeah. Well, you're definitely spot on because it was the last thing I remember. It was the last element of our relationship that had been conflict that we hadn't talked about since he'd gotten sick. Like, there had been other mistakes I'd made, decisions I'd made that we hadn't talked about, that over the last years of his life, I brought up, or he brought up, and we talked through, and we both got into this place where we're like, that's done, you know? It's that is, that no more holds any power in how I think about you, or how I think about our relationship. But the, but the fight outside CVS had gone unaddressed.

• 52:43Ryan Holiday?

  Yes.

• 52:44Speaker 01

  And, and it was still, I assume, this thorn in his mind about, okay, well, we talked about this thing, we talked about that thing, I regret that, I regret that. And we had gotten it all out, except this one thing. And you're completely right in that enough in those, it was such a fascinating case study of like those last forty eight, seventy two hours, like the things we were talking about.

• 53:06Ryan Holiday?

  Yeah.

• 53:07Speaker 01

  It was just, it was just reliving memories, all, you know, reliving memories, reliving stories and making sure any thorn that had existed got pulled out. And it was all relationship, always.

• 53:18Ryan Holiday?

  Like I, I think about like with my wife, like let, let's say I was to list like the fifteen biggest fights that we've ever had. I don't think there's a single one that I'm like, I would still die on that hill. Right? You know what I mean? Like, none of them matter in retrospect. Right? And so we get so worked up about things and then they, it becomes this sort of feedback loop. And then all of a sudden, yeah, you're having a fight outside CVS and fifteen years later, it's, it remains unaddressed, you know?

• 53:49Speaker 01

  Yeah.

• 53:50Ryan Holiday?

  And I think death puts all those things in perspective.

• 53:51Speaker 01

  Yep. And that was what we were watching him do was putting everything in perspective.

• 53:58Ryan Holiday?

  And he, and yeah, it was very courageous that he did that because he could have shoved you all away. He could have shut down. He could have focused on the pain that he was feeling or the, the, the, the biological struggle that he was in. But instead he went at a higher level and le- left a, a legacy in that sense.

• 54:18Speaker 01

  Yeah. And, and we have, we have stories now that we tell or jokes that he created from those last forty eight hours. Right? Like this, like, just, you know, you can imagine as someone, you're trying to read someone's lips to glean what's insightful to them in their last forty eight hours. But you're also going to have some mishaps in that, in that process.

• 54:42Ryan Holiday?

  Yeah.

• 54:43Speaker 01

  And even that, even that process and that community that we had in those last forty eight hours is now a legacy that he left. Because he decided to not, he decided to show up in those last forty eight hours in the best way he possibly could and engage and be present and want to share with us as best he could by lip reading and winking and staying awake as much as he could, like the things that were mattered to him. And now we, now we have memories that come from that that are beautiful.

• 55:16Ryan Holiday?

  Yeah.

• 55:18Ryan Holiday?

  The Stoics would probably love the absurdity of it, though, and I hope this isn't making light of it, but that one gets to this horrible place where you are deciding to die, right? And what does it say about life and modern life specifically that then the holdup is bureaucratic paperwork? That administrative work then determines when you're allowed to leave life on this planet?

• 55:46Speaker 01

  Yeah, it's not funny now in retrospect, but I'm grateful for those 48 to 72 hours. But the comedy of my dad finally, after like putting, going through so much with ALS, finally saying, "I'm surrendering. It's best for me, it's best for you." You know, and we had to lip read him saying, "I want to die." And then we have to go back to him after we meet with everybody in the hallway, you know, the doctors, the hospital administration, we have to go back to him and say, "So it's scheduled for Monday." And meanwhile, it's Friday. And so, just the amount of frustration that he had to be like, "So now I have to live

• 56:31Speaker 01

  with the knowledge that I'm gonna die on Monday?" That's a special kind of bureaucratic bullshit that has to happen.

• 56:37Ryan Holiday?

  Yeah, you get to a place where you say, "I want to die, I'm ready to die." And then the lawyer say, "Not so fast."

• 56:43Speaker 01

  Exactly. It doesn't look so good for us. We have to clear all the red tape.

• 56:48Ryan Holiday?

  Have you read the Springsteen biography, Born to Run, his autobiography?

• 56:54Speaker 01

  There were two, and I read the Bruce one by Carlin.

• 56:59Ryan Holiday?

  Oh, so I'm talking about the autobiography, the one that Bruce wrote?

• 57:03Speaker 01

  I think I've read both, but I only know for sure that I've read one. But go for it anyway, because I'm a big Bruce fan.

• 57:10Ryan Holiday?

  I was just thinking about it because there's so many Bruce Springsteen quotes in the book. And I was thinking about this scene in the book where, where I think it's Clarence Clemons, the saxophone player is dying of cancer. And that sort of the whole East Street Band is there in the hospital room as he's dying. And they sort of like, sort of what's, what's one last song that you want to hear? And they all play Sandy, like Fourth of July at Ashbury Park. And I, I remember thinking that, I think about it all the time. Whenever I hear that song, I go like, that'd be a good way to go. Like, just like of all the songs surrounded by the people that you love, that you worked with your whole life, to hear a thing you participated in making, that's pretty good.

• 57:54Speaker 01

  Yeah, that's pretty, I mean, I, I don't know why Sandy in particular compared to any other of the East Street Band songs, but it does have a nice, like melancholy undercurrent.

• 58:04Ryan Holiday?

  Yes, that's what I mean. Yeah. You wouldn't, you wouldn't, you wouldn't go out to like Born in the USA or something, right? Like, that, that's not the right, and darkness on the other side of town or something like, you know, that's not, but there, there is just a sort of a, like, at the end of it, that, I don't know, there, there's something that, that struck me. I, I don't know why I thought of that scene when I was, when I was reading the end of your book, but that something about that song struck me as, as, and then the, the scene of, of, of him going out to it.

• 58:34Speaker 01

  Yeah, no, actually, I think that that song Sandy is very representative of what the energy of the last 48 hours with my dad was, because there's like the sadness undercurrent, but there's the, the reminiscing about the beauty of life.

• 58:50Ryan Holiday?

  Yes.

• 58:50Speaker 01

  And, and that song is a, from what I remember of Sandy, I haven't played in a couple of years, but it's very much about a relationship and, and love in a time and place. And so all of that wraps up into a very nice little microcosm of life.

• 59:06Ryan Holiday?

  Yes, yeah, it's a, it's a song of nostalgia and love that's gone. And that's what, yes. I had a couple of other questions sort of related to this, but that I thought of lessons from the book. So you talk about the decision to leave ESPN, which we talked about when we talked about last time. But I, then reading this book, I saw another layer on it, which is your dad, you said your dad loved you working at ESPN more than you did, or it was more important to have you work at ESPN to your dad than it was for you to work at ESPN, as far as identity goes. And there's been parts of my life where I've noticed,

• 59:46Ryan Holiday?

  like, I go like, man, I sort of checked off a bunch of boxes. Why these specific boxes? Is that because I chose them? Like, am I interested in X, Y, and Z because I chose it? Or did I not even inherit that? Did I pick that target because I wanted something from these people? And do you find that some of the things, whether it's even basketball, that you did things because you wanted a connection with this person that was maybe there all along, or that you should have gotten other ways?

• 1:00:23Speaker 01

  I think that that is accurate, but with one layer removed, in that I think I started playing basketball because I adored my dad and I wanted to spend time with him. And that was the thing he was doing, therefore, that was the thing I was going to join him on. And then I was going to practice and get better at it because he could be by my side doing it. And I think that making those choices when I was just a little kid, then very much led me on a course where sports became the defining characteristic of my

• 1:01:01Speaker 01

  life. And then that led to, after college, pursuing sports journalism because I already had this background of having played with my dad, and then played in high school and played in college. And then that leads me to ESPN. And so, all of who I was in life up until my dad died, was a repercussion of...

• 1:01:26Speaker 01

  Wanting him to love me.

• 1:01:27Ryan Holiday?

  Yeah.

• 1:01:28Speaker 01

  But and he did love me and he liked me a lot. So it's not like I was chasing after some love that wasn't there, but it and then the older I got, the farther away I got from like what I really wanted. And it was more like, well, this is an echo. It was nostalgia. It's like an echo of a choice I made when I was eight.

• 1:01:46Ryan Holiday?

  Yeah.

• 1:01:47Speaker 01

  I mean, seriously, my career to his family was an echo of wanting to make him proud on the basketball court when I'm eight years old.

• 1:01:55Ryan Holiday?

  Yeah.

• 1:01:55Speaker 01

  And and I think that that is not a bad thing, but you do lose when it's that far removed from what you actually genuinely are in love with or care about. When it's that far removed, it's time. It's time to like reassess and and refocus on like, okay, now that I'm, you know, at the time I was 37. Now, what does 37 year old me want? Not as an artifact of eight year old me.

• 1:02:22Ryan Holiday?

  I think this is why Gatsby is such a beautiful book and why it's resonated now for almost 100 years. Is there this idea of the guy trying to get either back to a thing or try to capture this thing that you can't possibly capture, you know, sort of the boat beating ceaselessly back against the current? That's what we're all doing. Sometimes it's trying to go back in time. Sometimes it's trying to bring someone back from the dead. Sometimes it's trying to win the love of someone that you should have had inherently, naturally, never had to earn. Maybe it's not love, you know, because as you said, you know, your parents love you, but it's usually like pride. You want them

• 1:03:00Ryan Holiday?

  to be proud of you. So you end up orienting your entire life around trying to earn something that by definition should not have to be earned. And it's kind of the trap, the beautiful tragedy of a lot of high achievers.

• 1:03:17Speaker 01

  Yeah. And and the thing that comes off of it is for me that. I now, I don't think there's any way to reset if even if I wanted to.

• 1:03:30Ryan Holiday?

  You can't become a doctor now.

• 1:03:31Speaker 01

  Yeah, and there's like, there's no way you can unprogramme me from being an athlete and with that past and those skillsets.

• 1:03:41Ryan Holiday?

  Yes.

• 1:03:42Speaker 01

  So it's like, so yeah, I leave ESPN to go help my dad, but like now I now I work at Metal Arc Media, which is started by the former president of ESPN. And so it's like, it's not as if that experience then reset me completely and I'm on a completely different trajectory now because you, I think you can try to shape, reshape the experience of your childhood and like bring in things that are more in tune with who you are now, but it's, but it's still the skillset I have and who I was at nine is still programmed in there so deeply. I can't get that far away from it, I feel.

• 1:04:20Ryan Holiday?

  Yeah, it's like you still do the same profession, but you want to get to a place where you're doing it from a place of fullness as opposed to emptiness. Like emptiness is if I win this award, if I become this person, then mommy or daddy will be proud of me or love me or whatever. You, you sort of, you have to get to a place where you're like, okay, that is independent of what I do professionally, even if that's why I entered the thing to begin with and realising that no amount of accomplishment, nothing is ever going to get you that. And that you have to do the thing because you're like for the pleasure of doing it or because you like doing it or because you're good at it or because it's lucrative. You have to find a new reason to do it because the old reason is, is a heartbreaking

• 1:05:05Ryan Holiday?

  reason to do it.

• 1:05:07Speaker 01

  Yes, the old reason is, or when people, you know, and this might be just be a movie trope, but like they're marrying someone to piss their mom off. Like, these are all things that people do. And thankfully, my form of this was more, oh, my dad loved a sport and so I played that sport, which is, which is, I think, a thing that probably a lot of people can relate to, whether it's a sport or an instrument or something like that. But I still can't get away from that. I, I, I can't. I can only, within the skillset I have and the things that motivate me, try to find, try to find projects within that field that I feel more fulfilled by, like you said, than.

• 1:05:53Speaker 01

  Then what I entered, my motivation entering was probably more like, oh my God. But it's, everyone thinks sports are so cool and I'll be super cool to my dad and to everybody if I do this thing. And that's not sustaining.

• 1:06:06Ryan Holiday?

  Yeah, yeah. All right. So last question for you. So when I was wrapping up the Malcolm Gladwell interview, I decided to touch the third rail and talk to him about vaccines in sports. So I wanted to touch a third rail with you, which is something that I've seen you tweet about it. So I'd be curious, um, what is, I'm trying to understand the logic of it. Cause I, I, I would identify probably as sort of a centrist, maybe a little bit center right. But there's so many people that I know that are sort of conservatives, Republicans that are, that are good people and compassionate people, sort of love thy neighbor people. Why are people so worked up about this transgender sports issue? Like

• 1:06:48Ryan Holiday?

  I, I'm trying to think about it from the perspective of, like, I get why transgender people care about it. It's very important to them. I can't understand why someone who has never given a shit about women's sports ever before in their life, suddenly has very strong opinions about who should be allowed to be in women's sports.

• 1:07:11Speaker 01

  Well, I think, I, the way I saw this form, as someone at ESPN and now, now paying attention to these, to these topics in sports, it started first as the, like, North Carolina anti-gay bill that, that got passed. And then there was one in Indianapolis and Indiana. And like, even the, the NBA all-star pulled out of Charlotte one year because of like a bathroom bill. And it seemed as if... In the world of politics, it was like this, let's get everybody on board for these bathroom bills. And then those didn't seem to catch on.

• 1:07:55Speaker 01

  And it seemed to me as a political talking point to pivot from bathroom bills. Okay, that didn't work, but we need a lightning rod issue that will galvanize everybody

• 1:08:04Ryan Holiday?

  Yeah.

• 1:08:05Speaker 01

  to one side. And you could slowly see it over the course of a year or two pivot to trans issues in sports. And then the rallying cry became

• 1:08:16Ryan Holiday?

  Interesting.

• 1:08:16Speaker 01

  defend women. So one, from a political perspective, you could see it go from, okay, well, we're not galvanizing enough momentum and drawing enough people to our side with the bathroom bills. It's not working. Let's pivot to trans issues in sports. And I think that's working right now. So there's, there's that whole piece of it to begin with. That's kind of what has happened. There's the larger question about, okay, well, even though I don't think this is a problem right now, as someone who pays attention to sports, I think there's like, you know, you could, you could come up with maybe two incidents where you're like, maybe there's some fairness questions here.

• 1:08:51Ryan Holiday?

  Yeah.

• 1:08:51Speaker 01

  But it's not an actual, like, it's not an issue right now. But I, I will allow for the fact that over the next generation or two, it's something we need to understand how we're going to,

• 1:09:02Ryan Holiday?

  Yeah.

• 1:09:02Speaker 01

  you know, respond to. I think the question that I, that I think women's sports has right now as a protected class of sport is that when we defined sports, you know, it was like, first it was just sports and then our, our, our culture evolved and we're like, well, we want women to play sports too. Therefore, we're going to have a classified part of sports, which is women's. When we did that,

• 1:09:26Speaker 01

  gender non-binary and, and transgender in sport wasn't even a conversation. So we might've defined sports differently if 40 years ago, gender non-binary was more of a conversation topic and trans issues in sports were being talked about. We would have said like, well, let's define this category differently. And that, so I think, so I think now we're in this place where like it's women's sports and we, we've defined it as such. I think we need to have a redefinition. So that's my perspective, having watched it evolve.

• 1:10:00Ryan Holiday?

  No, I'm glad you said that because I think that's something that thinking sort of good people have to be really careful of, which is, let's say there's a certain amount of just like dark, toxic energy out there that human beings are capable of, right? We're suspicious, we have, you know, racial biases, we have, you know, the repugnance or disgust we feel about things. There's a darkness in human beings and it's usually directed at things we don't understand, things that are different or whatever, right? And when you do something like a bathroom bill, where that fails is it's like, who gives a shit, right? Like, I remember there was an SNL joke where it's like, you know, you can just go to any bathroom you want. There's no like police, right? Like, no one

• 1:10:42Ryan Holiday?

  polices the bathroom. He was joking, he was joking that you're sort of like enforcing a thing that you're writing a log about something that would never, ever actually be enforced because like people go to the bathroom for two minutes and then it's over and the crime, the crime has been committed and it's possible to have stopped. So that dark, the dark energy was manifesting about something that wasn't palatable, so it didn't get any resonance. But the sports thing, people have kids, people are hypersensitive about advantages between their kids and other kids. And so it's kind of like that

• 1:11:22Ryan Holiday?

  thing where, where like if you, let's say 40, 50 years ago, if you expressed some overt racial bias, maybe people would have said, hey, that's gross. But then where manipulative politicians would come in would be like, obviously, you know, people should be treated fairly, but would you want one of them to date your daughter? You know, like, it's, so it's taking the disgusting, horrible energy that you shouldn't divulge, you shouldn't indulge, and it's finding a way that it makes it more palatable, socially acceptable, so then it can be a wedge, then it can manipulate people, then it can make you do something that's bad, but that you could still look yourself in the mirror and be like, I'm not a bad person.

• 1:12:03Speaker 01

  Yep. And that right now is how, how I see the, the trans in sports issue is a wedge issue. It's a political wedge issue that is being... The the dark energy, it's shifted to that and now it's, you know, it's now it's the rallying cry. Um, so.

• 1:12:19Ryan Holiday?

  Because because who would who would become transgender to get a slight edge in women's sports? You know, like, it's a preposterous accusation.

• 1:12:29Speaker 01

  It's preposterous. And it's very similar to as someone who pays attention to these things in sports, like, one of the last bastions of, you know, misogyny, racism, and sexism that that you can that you can exhibit without being called out is just by outwardly aggressively hating the WNBA. Like, if you're going out of your if you're going out of your way, responding on Twitter, like, if ESPN puts up a post, like, you know, Tina Charles of the New York Liberty scores 32, and you're going out of your way responding to that tweet by saying, get back in the kitchen, or who cares? It's the last place where you can just be misogynistic.

• 1:13:11Speaker 01

  You can place your misogyny, or your racism, or your homophobia, and closet it behind, I just don't like the WNBA. And I think that there's a lot of issues in sports that exist like that. Like, this, the trans issue in sports, it's not really about, quote unquote, defending women's sports, it's about your own fear of the unknown.

• 1:13:32Ryan Holiday?

  Yeah, or it's really, the idea that, like, men and women are not, like, that, as a man, the the idea that men are superior to women is culturally not an acceptable idea to discuss or to to put out there, except the idea that men are better than women at sports. So the joke about, like, you know, men will say, like, oh, I could play in the WNBA, or whatever, right? That's, you you wouldn't say, oh, I could be a better CEO than, you know, the a female CEO of a of a Fortune 500 company. But you can, it is culturally acceptable to talk about how you're a better athlete than women, because historic, or, you know, that some of the the times of male sprinters are, or female sprinters are equal

• 1:14:17Ryan Holiday?

  to, you know, X, Y, and Z, of course, an unequal corresponding male time.

• 1:14:23Speaker 01

  Yeah, the biological athleticism of of men is superior to women. Therefore, if you want to take that to its natural conclusion, then you've got guys now saying that they can beat Sue Bird in one on one because they played in middle school, which is really just their way of exerting their, like, whatever inferiority they might feel and threat they might feel by just the mere existence of the WNBA. But but the the trans issues in sports, like, it's not that I'm positing that it's not something we all need to, who are involved in sports, we need to be thinking hard and deep about it. Because I mean, I heard Malcolm talking about, you know, like, the, obviously, 3% in sports

• 1:15:06Speaker 01

  is a huge amount when it's in running or swimming. So if you're saying that testosterone levels are at a certain place and someone's only having a marginal advantage, it's like, well, that, you know, the Olympics are about margins. So it's not as if I don't think we need to be talking about this. I just think that we had, the thing I said earlier, like, these classifications that we've created were created in a different time period. And I don't think any of us, like, an answer to this question isn't, well, some people won't be allowed to compete. I don't think that that's a place we want to get ourselves. So I think we need to really start thinking long and hard about how we're how we're reclassifying

• 1:15:47Speaker 01

  what what sports are and how we're going to Olympics, to WNBA, because even this is an issue even within the WNBA with gender non-binary and transitioning and how how the WNBA is even going to classify itself.

• 1:16:02Ryan Holiday?

  It's so strange, too, given that we just sort of came off, that's a weird way to say it, but that culturally or globally, we've come to an evolution as an understanding of of of of gay rights and and and what it means to be gay and what it means to go through that, that, like, people's instinct on this transgender thing is like a suspicion.

• 1:16:29Ryan Holiday?

  Or like an anger towards the people, right? As if they're like trying to pull one over on you as if this is like a thing that they're like wanting to do or that it's like an. It's weird that our default reaction is like a is like a defensive one when really it should be an empathetic one because if you think for two seconds about what that experience is and what it must be to be a minority of a minority of a minority. I don't think your reaction is like, how do I prevent this person from doing what they're trying to do? You know what I mean?

• 1:17:08Ryan Holiday?

  Like, because not only are the stakes like pretty low, but like from a human being perspective, like I don't, I don't, it's, it's striking to me that our reaction is such, such a negative one when it really should just be a like, that must be very hard. Like, it must be very, very hard to be you. So what do you need?

• 1:17:33Speaker 01

  Yeah, I, I, I do, and it's, it's almost like a cliche to suggest like media messaging. But I mean, I, when I, growing up, I saw Joanna Man. Like, that was a Hollywood movie about, about a guy pretending to be a woman so he could dominate in the equivalent of the W, the WNBA. And a lot of our, I mean, a lot of our media around trans issues is pretty bad. I mean, go back to, go back to like Silence of the Lambs, go back to Psycho.

• 1:18:11Speaker 01

  I mean, the, the portrait we have, the portrayal we have about, about like trans women in media is one that like, it's almost like a default inside our brains that like, oh, you should be, like, this is a dangerous, scary situation. And that has been happening, like in, in, in movies and in storytelling for a really long time.

• 1:18:36Ryan Holiday?

  I didn't think about that. Yeah, so people have sort of been programmed that it's this like, yeah, again, aggressive or deceitful thing, when of course, even if it was based on deceit, because I mean, let's say people are trying to pass, they're not trying to pull one over on you, they're trying not to get beat up by strangers. Like, it's not, it's so interesting that we, we perceive minorities asking for what's theirs, like what everyone is, we see that, it's like that joke about how when you're used to privilege, you know, equality sounds like

• 1:19:12Ryan Holiday?

  a step down, that we perceive what they want as, as zero sum, when it's not zero sum at all. It doesn't affect you in any way, first off, because you don't play women's sports, second of all, because you don't watch women's sports, but third, because like, when things are better for other people, they're better for, for everyone.

• 1:19:35Speaker 01

  Yeah, and I know this is completely, we're off on a topic here, but I'm fine to be off on it, in that we can say that, for people who are casually paying attention, they can say, well, you know, trans, trans issue in sports, like, well, let's just, let's just, no trans people can compete. Well, what are we going to do then about like, intersex athletes? It's not as if, it's, it's not, I'm not saying those, those are the same thing, but I'm saying this is all about a classification, and it's all based on the premise that, like, sex is always binary, and it's just not. So we're either going to live, we're either going to live in a world in which we say, well, we created sports as binary,

• 1:20:20Speaker 01

  based on like, the idea that we all said and perpetuated that sex is only binary, and like, anyone who falls into any kind of middle ground, like, we just don't have the capacity as a society to deal with it, like, are we, we're either going to be that society, or we're going to say, well, let's, let's actually go back to the drawing board on this classification of women's sports, and see how we can restructure this.

• 1:20:45Ryan Holiday?

  Yeah, and there's a thing from a media perspective that I think people miss that it's worth pointing out. There's this thing called concern trolling. Do you know what that is?

• 1:20:54Speaker 01

  Yes.

• 1:20:55Ryan Holiday?

  Where you pretend to be concerned, but really you're just using the fact that the other person will care that you're concerned against you. Like, I remember I was, I did a Fox News interview not that long ago, and like, so, you know, you have to watch like the segments before you're on. And the segment was about some law in California that allowed like prisoners who identify as this or that to go to the prison of their choice. And it was all about how now all these vulnerable women, female prisoners will be exposed to people who are pretending to be women. And it's like, first off, is there any evidence that anyone has ever done this? But I was like, second, like, since when did you care about inmates in prison? Like, you don't actually give a shit, right? Like, you don't

• 1:21:37Ryan Holiday?

  give a shit at all, and now all of a sudden you're white knighting for these female prisoners in California. And it is, and that's saying it's not an issue. You do have to decide like how you protect, you know, people in prison. And are there prisoners who lie to try to get certain advantages and fucked up things happen in prisons? Yes. But like, you're concern trolling right now to use this as a wedge issue to keep people divided. And I think it's hard for people to recognize sincere anxiety and worry and sort of that dark energy anxiety and worry, which is designed to make you suspicious of someone or some other group.

• 1:22:20Speaker 01

  Yeah. Oh, just one more quick addition to that, because it's like, most, even going back to the bathroom issue. Most trans women that I know, and having, you know, looked at this issue and read it a lot, like, most trans women will go out of their way not to go in a public bathroom, because they don't want to make, they don't want to be in that situation. They don't want to make women in the bathroom, cis women in the bathroom, uncomfortable. So, most, most trans women will like, make sure they use the restroom before they go to an airport, so that they're not putting anyone in a situation where there's discomfort. So it's like, the fact that we're trying to pass a bill...

• 1:23:04Speaker 01

  About this thing that you think is going to happen when the people that you're passing it against are purposely trying to spare the feelings of cis women is like it's it's all back to the dark energy that you talked about.

• 1:23:16Ryan Holiday?

  Yeah, no, and it's it's sad that whatever we have going on as a society from a media incentive standpoint to a, you know, like polarization standpoint that like that dark energy is like kind of the through line of all our conversations for some horrible reason.

• 1:23:36Speaker 01

  Yes, yes, because the dark energy causes you to click and read about it and those are the advertising incentives. Yeah. And so whoever can manipulate the dark energy best.

• 1:23:46Ryan Holiday?

  Yes, yes. And both and both sides do do it, right? Because anger is a viral emotion. So so in the one hand, someone's using the the wedge transgender issue to to get attention. And then the other side is using the reaction about what the fucked up thing the other people are doing to get attention. And then we're all missing the fact that these are human beings who constitute like a miniscule percentage of the population that present a threat to no one who are, by the way, just trying to be fucking happy and figure out how they can do the best at whatever it is that they feel like doing. It's not it's so insane.

• 1:24:24Speaker 01

  Yep, yep.

• 1:24:26Ryan Holiday?

  Well, let's let's not wrap up on that. No, let's wrap up on the book. Any any what do you feel like coming out of this? How how did going through what you went through shape who you've what you've gone through over the last year, let's say, like coming out coming? It's sort of you got, I guess, you know, when it rains, it pours. You went through this thing with your dad and the pandemic. And then now, whatever this weird half reopening, uh, normal life thing that we're in. How has this changed who you are and where you're going?

• 1:25:01Speaker 01

  So the book, and well, and just taking time with my dad, it completely shifted how I think about career and life. And by that, I mean that I definitely adopted this idea that like life is tracks. And like you gotta, you know, if you get off, we have that saying like, oh, you got off track. And it insinuates that there's like a singular track that we should all be on. And it just has really opened my eyes to being, being able to step back and step away. And that doesn't mean that you're either moving backwards or moving away.

• 1:25:46Speaker 01

  Because I leave ESPN, I spend this time with my dad. I feel like I'm a better version of my professional self than I was before. And so it's, it's really, I'm not sure how I'm going to apply it yet. Whether I want to be someone who maybe works for, you know, three years and then takes a year off. You know, I, I just, I want to do something differently than assume that the point of my life is to get back on the ladder or the track and then move forward for the next 15 years until, you know, well, hopefully I have that long. My mom gets sick and then I have to learn the lesson again. Like, no, I, I'm not waiting for any other time period now.

• 1:26:30Ryan Holiday?

  Yeah.

• 1:26:31Speaker 01

  I, I don't, I'm not buying into the messaging of that careers define you and that you should be. And I know you've talked, I think you've talked to Tim Ferriss about this a lot. Like, if there's some other life you're waiting for, then you're, you're doing it wrong. Like if this, you're doing this thing so that someday you'll have this thing. I don't want to be that person anymore.

• 1:26:51Ryan Holiday?

  Yeah, and you already live in a small town, sort of like me, although Charleston's bigger than where I live. But the job transition, the where you live transition, I think when we're looking at these trends now of like raising house prices in all these new places and, you know, employers having trouble hiring people. I think people woke up, you know, June or July of 2020 in the depths of the pandemic and they were like, I fucking hate where I live. I fucking hate what I do for a living. Why am I gonna keep doing this? You know? It's not an incentive. So it's not incentives. It's not like, oh, you know, wages haven't been rising enough. Although, let's say that's true. That's not why people are suddenly quitting their job and moving to Montana.

• 1:27:35Ryan Holiday?

  It's that they were like, they got a, they got, they got the kind of perspective shift that you got going through this thing with your dad where you have to step back and look at your own life from a slight distance or moment of stillness and you go, I don't want to do it like this.

• 1:27:52Speaker 01

  Exactly. Yeah. And it's like the emperor has no clothes, if I'm using that metaphor correctly. Like, we all told ourselves, like, what would happen if work, if we weren't working? Or what would happen? Nothing. Nothing. Nothing happened. I mean, obviously, people kept working, but for this kind of like, the career achievement obsessive workaholics, you think the world would stop if you stopped doing your job? No. And so that, I think I got that perspective from my dad and then the pandemic on top of it. Like, I don't, I'm not here to work. That's not, that is not what I'm here to do. And that is a completely different shift than I, than I had before.

• 1:28:35Ryan Holiday?

  No, that's beautiful. And then, yeah, your dad shows that you don't even know how long you're here for. So you should do it while you can.

• 1:28:42Speaker 01

  Yeah, that's right.

• 1:28:44Ryan Holiday?

  Well, this is amazing. I'm so glad we got to talk. I love the book.

• 1:28:49Ryan Holiday?

  Thanks so much for listening. If you could leave a review for the podcast, we'd really appreciate it. The reviews make a difference, and of course, every nice review from a nice person helps balance out the crazy people who get triggered and angry anytime we say something they disagree with. So if you could rate this podcast and leave a review on iTunes, that would mean so much to us and would really help the show. We appreciate it, and I'll see you next episode.