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What It Means to Be on That Hill | Seth Wickersham

September 19, 2026

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5 min read

What It Means to Be on That Hill

Bruce Springsteen sings a line in the last verse of the last song on Darkness on the Edge of Town: "I'll be on that hill 'cause I can't stop / I'll be on that hill with everything I got." For ESPN writer Seth Wickersham, that lyric became a kind of prayer. When he collected two decades of his best magazine stories into a new book, he realized that every piece was about the same thing—people struggling internally to achieve something, showing up when it's hard, when no one is watching, when the outcome is uncertain. The hill is not the summit. It's the willingness to keep climbing.

The Unifying Theme: Internal Struggle

Wickersham's working premise, as he put it, is that his stories are "all about internal struggles of people trying to achieve something." The athletes and coaches he writes about are not simply competing against opponents. They are wrestling with their own ideas of themselves, with what they could become, and with the possibility that those visions might be in peril. The question that runs through the book is: how do they go forward, and how do they reconcile with what they find?

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What you'll learn

  • 1 (00:00) **Introduction** - Ryan Holiday introduces the episode and the theme of "being on that hill," drawn from a Bruce Springsteen lyric.
  • 2 (03:49) **What "Being on That Hill" Means** - Seth Wickersham defines the central metaphor of his new book.
  • 3 (07:52) **The Scarcity of Slots in Sports Writing** - Seth connects the struggle of athletes to the struggle of writers trying to make it in a limited field.
  • 4 (12:12) **The Difference Between "Making It" and Superstardom** - Ryan and Seth discuss the role of luck in success and why the goal should be just to get on the hill.
  • 5 (16:03) **Tom Brady’s Changing Perspective on Luck** - Seth illustrates how success can erase the ability to see one’s own luck.
  • 6 (18:00) **The Necessity of Self-Mythology** - Ryan and Seth explore how successful people lose sight of alternate realities.
  • 7 (19:13) **Competitiveness in Sports vs. Writing** - Seth reflects on the different roles of competition in athletics and creative work.

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Show Notes

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: 


🎶 Lyrics are from Darkness on the Edge of Town - Bruce Springsteen


Seth 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 Nonfict

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