What It Means to Be on That Hill | Seth Wickersham
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What Springsteen lyric inspired Seth Wickersham’s book “Be On That Hill”?
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. Took 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 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 wormed 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 wormed 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.
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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 Sisyphus, 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 and 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's written about, about who he aspires to be as a writer, and all the things it evokes, right? Ambition and obsession and perseverance, what it costs to keep climbing that hill, what it costs to try to stay on that hill. Whether you conquer the hill or not is not up to you, I think the Stoics 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.
How does the “being on that hill” metaphor define showing up and paying the price?
And you can follow him on Instagram and on Twitter at Seth.Wickersham. And you can pick up copies of Beyond the 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 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, 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. And so... You know, I love Springsteen.
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Chapters
8 chapters
1
What Springsteen lyric inspired Seth Wickersham’s book “Be On That Hill”?
0:00–3:25
2
How does the “being on that hill” metaphor define showing up and paying the price?
3:25–6:13
3
Why does Seth say luck and “black‑swans” matter as much as hard work for success?
6:13–9:58
4
What was Seth’s early career path and how did he finally land at ESPN?
9:58–12:38
5
How does Seth view competitiveness versus collaboration in sports and writing?
12:38–15:19
6
What internal struggles do elite athletes and writers face while chasing the hill?
15:19–17:44
7
How does Seth balance ambition, discipline, and the acceptance of outcomes?
17:44–21:22
8
What practical lessons does Seth share for staying motivated when the work gets hard?
21:22–25:36
Speakers
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