The Daily Stoic - What It Means to Be on That Hill | Seth Wickersham

Episode Date: September 19, 2026

How do you keep climbing when there’s no guarantee your work will pay off? Sportswriter Seth Wickersham joins Ryan to talk about the Springsteen lyric that inspired his new book Be On That Hill, the role luck plays in success, and what keeps ambitious people showing up when the work gets hard. 📚 Books Mentioned: Be On That Hill by Seth WickershamIt’s Better To Be Feared by Seth WickershamAmerican Kings: A Biography of the Quarterback by Seth Wickersham 🎶 Lyrics are from Darkness on the Edge of Town - Bruce SpringsteenSeth Wickersham is a senior writer at ESPN and the New York Times bestselling author of Be On That Hill, It’s Better to Be Feared: The New England Patriots Dynasty and the Pursuit of Greatness, American Kings: A Biography of the Quarterback. Focusing primarily on longform enterprise and investigative work on the National Football League, Wickersham has been a finalist for the National Magazine Award for Reporting, and his stories have been anthologized in the Best American Magazine Writing, the Best American Sports Writing, and Next Wave: America’s New Generation of Great Literary Journalists, among others. Released in 2021, It’s Better to Be Feared was named Nonfiction Book of the Year by Sports Illustrated and Best Sports Book by the National Sports Media Association. Follow Seth: X & Instagram: @Seth.WickershamGrab copies of It’s Better to Be Feared, American Kings, and Be On That Hill at The Painted Porch | https://www.thepaintedporch.com🎟️ DAILY STOIC LIVE | Ryan Holiday is coming to a city near you! Grab tickets here |  https://www.dailystoiclive.com/🎙️ AD-FREE | Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail--Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are.--Wealthfront’s high-yield cash account: https://www.wealthfront.com/stoicThis experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Ryan Holiday, who’s a client of Wealthfront, receives cash compensation from Wealthfront Brokerage for paid testimonials in his podcast, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new clients) when you direct deposit $1,000 a month, plus open, fund, and maintain an investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms apply. Full details at wealthfront.com/promo-terms.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of January 30, 2026, is representative, requires no minimum, and may change at any time. References to the APY for the Wealthfront Cash Account, including any APY increase, are to the APY paid by insured depository institutions that participate in our cash sweep program (the "Program Banks”). Wealthfront Brokerage does not pay interest. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY.Instant and same-day withdrawals use the Real-Time Payments (RTP) network or FedNow service. Transfers may be limited by your receiving institution, daily caps, or participating entities. New Cash Account deposits have a 2–4 day hold before transfer. Wealthfront does not charge fees for these services, but receiving institutions may impose an RTP or FedNow Fee. Processing times may vary.. Fees & Eligibility requirements may apply to certain checking features.Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Investing involves risk, including the possible loss of principal. Securities investments are not bank deposits, bank-guaranteed or FDIC-insured, and may lose value.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome to the Daily Stoic Podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world. Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I am a Bruce Springsteen fan to my kids to see Bruce Springsteen here in Austin. A couple of months ago, I had to fly into New York to do a talk. I flew back. And I flew into JFK, flew out of Newark, and I was at the airport in a Bruce Springsteen shirt. And this guy's like, oh, my gosh, you're wearing a Bruce Springsteen shirt. And I was like, oh, yeah, I forgot. I was in New Jersey. But I think people who are Bruce Springsteen fans, there's just something about little lines,

little things that he says that just sort of worm their way into your brain. I talked, I think in the Daily Dad book, about this line that warmed its way into Johnny Cash's mind, that line about how there's nothing better than blood on blood. Well, my guest today, the sports writer Seth Wickersham, who's been on the podcast before, one of my favorite writers, also has a line from Springsteen that warmed its way into his brain, something he's carried around with him for years. And it's this line about being on that hill. Let me actually play the Springsteen lyric for you real quick.

In Seth's interpretation, that line is about showing up. It's about being willing to pay the price. It's about wanting something so badly, even when it's hard, even when no one's watching, even when you're not sure how it's going to turn out that you do the work. I do think there's something stoic in there, too, right? You don't control whether you win. You don't control whether people appreciate it. You just control whether you're out there doing the work.

You don't control whether you get to the top of the hill like Sisyvus, but you control whether you're doing what you're supposed to. be doing. Seth and I are going to talk about that in today's episode. It's a shorter episode, but Seth, who is a great writer at ESPN, is the author of It's Better to Be Feared in American Kings, which is a great book about the position of quarterback. And his new book, Be on That Hill, is two decades of reporting and writing about athletes and coaches and that pursuit of greatness, the people who are fighting to be on that hill. And in today's episode, we're talking about that phrase. Where the idea of being on the hill comes from, how he thinks it captures something

essential about the people he has written about who he aspires to be as a writer and all the things that evokes, right, ambition and obsession and perseverance, what it costs to keep climbing that hill, it costs to try to stay on that hill. Whether you conquer the hill or not is not up to you, I think the Stokes would say, but whether you're on it or not is. Seth has been a finalist for a National Magazine Award. He's been anthologized in some of the best magazine sports writing in this country. His book, It's Better to Be Feared, was a nonfiction book of the year by Sports Illustrated. And you can follow him on Instagram and on Twitter at seth.wikersham. And you can pick up copies of Beyond That Hill. It's Better to Be Feared and Love and American Kings at The Painted Porch,

which we have carried since before I first had him on the show because I am a big fan. I'll link to that in today's show notes. Let's get into it. Okay, so tell me about this idea of being on that hill, because it's sort of the through line of the book, but I think it's an interesting, it's an interesting concept. I've listened to that Springsteen song many, many times. I don't think that lyric ever jumped out at me. So what does it mean to you?

You know, when I collected the stories in the book and you try to find like a unifying theme, right? And my working premise at the moment, and I reserve the right to change my mind. But my working premise is that like these are all about internal struggles of people trying to achieve something. Yeah. And so, you know, I love Springsteen.

I have since I was a kid. And, you know, I go around and around about what album is speaking to me best at a moment. But I find when I'm in the darkest creative places, you know, that darkness on the edge of town speaks to me the best because it's not, it's an adult album. It was really his first adult album.

And, you know, when he sings that, lyric. It's at the last song and the last verse of the last song. And, you know, he says, I'll be on that hill because I can't stop. I'll be on that hill with everything I've got. And I'm like,

you know, that's the prayer. You know, that's the hope in a weird way. And, you know, he was once explaining that line and he said, you know, the setting for personal transformation is often found when we're at the end of our rope. And I really

you know, your work helps, you know what I mean? These, all these internal monologues that you're dealing with and you're wrestling with all the time. But those are, that's one of those lines that I can, like, I can cling to when, you know, you're just kind of creatively stuck or in a dark place and you have to figure out a way through it. So does being on the hill for you,

is that kind of the aspirational element of Springsteen where it's like, you know, I got to get out of this town, I got to make my mark. But then also it's like, I got to, conquer these demons. It's, it's sort of all of it and more of like, where I am isn't working, so I got to get there. Well, it also just showing up. You know, it's all those things. You know what I mean? But it's also just like, you know, whatever the thing is you need to do being there and being on time and, you know, being propelled by something that is kind of mysterious and depending on how you

talk about it can either sound like incredibly romantic and cool or, you know, incredibly annoying and precious. Yeah. But, you know, it's the, you know, again, it's all these internal forces that you have within you and where they take you. And, you know, being on that hill, you know, means, you know, you've kind of left some of those romantic ideals behind a little bit and you're showing up for whatever the thing happens to be. And that's kind of how I looked at it.

And, you know, when I was putting the other stories for the collection, you know, again, some of these things can sound kind of insufferable. So I'm trying to be careful. But what stood out was just how hard they all were and how, you know, I didn't want to ignore that. And so when I was kind of trying to, you know, write an introduction to it and introduce the ideas and the themes that I get at and the conversation, really, that happens throughout the book, you know, I kind of want to. to say without trying to say that it's harder for me than anybody else, because I don't think it is, just that these things are struggles, and they're all struggles. And everybody who I really write about in the book is, you know, struggling internally. And in some part, maybe their idea of themselves

or what they could become is in peril. And how do they go forward? And how do they reconcile with that and deal with it? Well, because I was thinking about it, because you do talk about this sort of, in the intro, you talk about sort of like the scene of writers. that you came up with, how few slots there are to actually be able to do what you do, which is obviously something that sports writers have in common with athletes in a way that maybe we don't think about it with like movie critics. Even though there's not that many movie critics, we don't go like movie critics and movie directors are both, you know, trying to be on that hill. For some reason, I think that's because maybe, you know, the role of the critics

seems to, you know, not always be to sort of celebrate and tell stories, but to sort of tear down or to say what's wrong. But I don't know, I related to that and I relate to it because, like, the phrase I always use, like, as a writer, like, I'm not trying to sell the most or be the most famous or what, but I am trying to be in the league. That's how I think about it. Like, I think about how many guys are in the NBA. Obviously, some leagues have more players than others. But I just think about, like, being in the league, that, like, hard work and a little bit of luck can get you in the league. Now, whether you're the Jordan of that league or the highest paid player in that league or, you know, on a championship team in that league, all these things tend to, at some level, be more outside your control than just, like, making it period. But I'm curious how you think about that.

Yeah, well, so when we were in college, you know, me, Wright Thompson, Justin Hecker, Steve Olentick, Tony Rehagen, all these guys who were just like fantastic writers and great friends, you know, we all had our different versions within the palette of what we wanted to do, but I think we all kind of settled on wanting to be magazine writers. Yeah. Like I think that's where we found the most combination of creativity and depth and, you know, timelessness, all these things. And so, you know, we would look at it.

the mastheads of magazines, kids, you can look up what a mast head is. Yeah. And, you know, the odds weren't good. You know, Sports Illustrated at the time had something like 28 writers. I think ESPN magazine might have had nine or ten. And then you're talking about the S-Quires and the GQs that have like seven or eight writers. So, you know, those odds are not good. And we kind of had a little bit of a blind faith that, well, we're the best things that, you know, that are coming up.

you know, we're going to do this, whatever it might be. And, you know, then writing as it always does will, you know, take a sledgehammer to that idea and make you work through it. But that was like kind of where we were coming from. It's like, how do we get from Columbia, Missouri to, you know, to the point where one of these editors and chief, who has a fancy office in Midtown Manhattan, you know, says that's the voice that I need.

So when I was applying for jobs, I had a really, at college, I had a really high opinion of myself. And I applied to like six places, right? Yeah. The New York Times, Boston Globe, Washington Post, ESPN Magazine Sports Illustrated. I think that was it. Right and I took a trip to New York to try to meet with those people and try to, you know, increase the odds. And like, you know, it wasn't going well.

And I printed up 40-some resumes and clips and cover letters to send out to just like every major metro newspaper because I, you know, it was coming up on not getting a job. ESPN called with an opening. They couldn't get me in the in right away, but, you know, just come here, we'll pay you, and then we'll hire you when we get clearance to fill this position. So I did that. And, you know, my parents weren't thrilled about it

because at the time, until I got brought in full time, it wasn't, you know, benefits, you know, that type of thing. It was a couple months without that. But like, if I had been offered a job by Sports Illustrated or the Washington Post, rather than ESPN, in that context, I probably would have taken them. I don't know for sure, but I probably would have.

And if I had, look, I probably would have been part of the Sports Illustrated layoffs at some point. I probably would have been part of the Washington Post closing at sports section. And so you look back on those things and you're just like, holy cow, was I fortunate to land where I did and, you know, be surrounded by the people that I was surrounded by? Because you can't predict that stuff. Yeah, there's a Nassim Talib thing that I think about all the time and I'm going to forget the specifics of it. But he basically says, like, you know, hard work can get you a professorship.

It can get you a BMW. You know, it can get you like a book deal or something like that. But he's like, luck and black swans are a private jet, you know, a Pulitzer or a Nobel Prize. Right? Like there's making it and then there's like superstardom and that, that like, we'd like to think that the difference between Tom Brady and and Tiger Woods and whomever and then the people in the, league that you've never heard of is just like they work that much harder. But it's not. It's a whole other set of circumstances usually. And then, you know, obviously there is a cost. Some people are willing to pay that other people aren't willing to pay. But that's why I like the title of the book,

it's like the goal should be to be on the hill. Like to necessarily make it to the top of the hill and knock everyone else off the hill and be recognized for being. Like all those things, you know, that's like a dream on top of a dream on top of a dream. But the core motivating force has to just be that main one. It's like, I want to get there, right? Like, I want to make it to the hill. I want to be on it. And then I'll figure out from there.

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Quince makes it easy to upgrade. Find your next fall favorites at Quince. Download the Quince app for app exclusive offers or go to quince.com slash stoic. You can get free shipping on your order and 365-day returns. Now available in Canada and the UK to Q-U-I-N-C-E.com slash Stoic. You know, I write about Tom Brady. I've heard about him a lot of my life. I've talked to you about him a lot. And he's, you know, some of my magazine stories on him are in the book. And there was two separate conversations I had with him that were about a decade apart. And the earliest conversation was, you know, he's just getting started. And, you know, the first couple years of his career just happened so fast. And he goes from zero to global

superstar just like that. Yeah. And he said to me, you know, I think of all the time, if I had been drafted by like the Arizona Cardinals at 198, rather than the New England Patriots of 199, you know, I might be out of the league right now. Yeah. And it was an interesting perspective to have when he was, you know, 25, 26, 27 years old. So then fast forward, I'm interviewing him as he's entering the back third of his career. So he's like late 30s. And I kind of referenced that.

And I, you know, I said, do you ever think about the randomness of your career, you know, and how easily it could have been someone else? And it was so interesting because his reaction was so different. I mean, he tilted back, he wear at his house, and he tilted back in his couch, and he just kind of stared at the ceiling, and I was like, and he goes, well, it was very defensive. Yeah, you can no longer conceive of you not making it, right? The story becomes too real. I was doing these things and the other ones weren't.

Yes. And, you know, there's a lot of truth to that. There's a ton of truth to that. And yet there's also the luck of circumstance. And, yeah, you know, and I think that, like, when you're talking about wanting to be, on the hill or, you know, I think you put it great, you know, I want to be in the league. You know, whatever it is, I hope that I'm one of those guys that, you know, yes, a lot of it comes down to discipline and, you know, choices you make and all these things, but a lot of it is

you have to be able to just kind of be at peace and kind of celebrate the fact that a lot of it's out of your hands. No, it's funny that Brady story is funny because in the Halberstam book on on Belichick, they talk about how they would keep that picture of Brady on their desk as a reminder that they didn't know, like, that they didn't actually make an incredible draft pick, that they thought they were picking somebody up who was worth more than, you know, the 199 spot, but they were not picking the goat. And I think that is a seductive part of the story as you get older and you get more accomplished. You lose the ability to conceive of the alternate realities or the other timelines.

which just as easily could have been true. The self mythology to a certain extent. And I think that to be successful, there's a part of you that has to self-mythologize. And you can sound incredibly precious and insufferable talking about it, or you can almost kind of sound endearing at times talking about it, but it has to exist a little bit within you.

And the people that I write about in the book, You know, they're extremists. And, you know, a lot of them are happiest when they're unhappy, which is, you know, another kind of like really prevalent theme in anyone who does creative work. Well, it's interesting with sports compared to, say, writing, like, obviously sports is driven by competition because it is a contest between you and another person. It's a contest between you and a record. There is this binary win-loss thing.

And so, you know, to get, not to stretch the metaphor, it's more of a game of King of the Hill, right? Like where you're driving to knock other people off the hill. Whereas what we do, or imagine your journey, that competitive drive, it's there a little bit because you're measuring yourself against your heroes and what you see as great work. And at the same time, it is not so zero sum as other things. So when you think about, like, getting to the summit, as you've seen it at athletes and then in your own life, how do you think about competitiveness? Yeah. I mean, you have to have an insane internal competitiveness. Like, I was always very internally competitive and very hard on myself.

I was never one of those guys that, like, when they lost, you know, was screaming and whining and all those things. It was more like self-loathing that took over. You know, when I was playing quarterback or playing basketball, you know, in high school, whatever might be. I think that, like, what I've learned, I think, in the course of, you know, writing and doing these stories is that, you know, if you define yourself by those zero-sum things, you're asking for a really tough existence. Because even the people who define themselves, you know, wins and losses, after Brady lost one of his Super Bowls, I think it was a Super Bowl. Kurt Warner texted him and he said, you know, being the best doesn't mean you win every time. It just means you win more than everyone else. And it meant a lot to Tom in the moment, even though, you know, he clearly defines himself

by how this, you know, winning the last game of the season. And I think as a writer, you know, there's a real balance between being competitive, being, you know, proud of what you do, and also being able to be happy for other people and celebrate their successes. And, you know, even if they might beat you out for an award or whatever it might be, I think that, like, the people that I see in my career who are writers who struggle with just being able to celebrate their friends and their peers who can't handle it, I don't know if that really helps them in any way.

Like, I don't think it's a differentiator. I think it's just like one of those things that they have to figure out a way to limit. You know, you can't unwire it for yourself, but you have to figure out a way to limit it. Well, that's the tricky thing because you're in the league of the people doing the thing, but you're also your own league, you're your own brand. Like one of my favorite lines of all time. I just sort of used to shape my career. The manager of Iron Maiden was once asked, you know, some question about the music business.

And he goes, I'm not in the music business. He says, I'm in the Iron fucking Maiden business. Yeah. And his point is like, I don't really care what the trends of the industry are going. it doesn't matter if somebody else sells a lot of records. Like, my job is to sell this band, right? Like, my job is to help this band to do what it wants to do. And I think that that is like an important lesson.

Like, you're not actually in publishing or the magazine business. Like, you chase the stories that you like chasing and you write them in the way that only you can write them. And then when you realize the logical conclusion of that is that actually there is no competition because there's no one doing what you were doing, right? Like you have this monopoly. Right. And so it becomes, yeah, much more this sort of personal, this sort of race or exercise

and maximizing your potential or realizing what you have within you or, you know, doing what you're capable of doing as opposed to, yeah, getting certain awards or, you know, having the biggest contract with this magazine or publishing the most stuff or the most reader. Like all that stuff is not actually a good metric of what you're doing. No, and it's also lonely. You know, and I think that like one of the things that I was really fortunate, I think you also, you know, to come up at an era where you can have access to perspective on writing very easily. Because writing is so lonely and it's such a, you know, that idea you just expressed of it being you and the keyboard.

And it's really like all of these things are ingrained within you. And it's the race, so to speak, is to get the best version of it out. And that can be liberating and it also can be debilitating. And, you know, going back to, you know, Tom, Juneau, or, you know, some of these, like, great writers who, you know, I think especially around, like, I want to say, 07, 08, 2009, 2010, there was just a ton of these websites that, came up that wanted to interview writers about writing processes. Yeah. And, you know, learning about Tom Juneau's writing process, who's, you know, might be the greatest magazine writer ever.

I mean, certainly, he's definitely in the league. And hearing about how, you know, difficult it is and how he fully scrap stories and starts from scratch and all these things, I think it's just reassuring in a way because, again, I've been to your office, you know, outside of Austin. You know, there's not a lot of room for other people. It's you in that office and that writing chamber. And, you know, it's what you make of it that day or what you're able to make of it. And I think that, like, having the ability to zoom out and to gain a little bit of perspective

in context for your peers or people you look up to and how difficult, you know, this craft can be has been one of the kind of enormous blessings, you know, of my professional life.