Episode · The Daily Stoic · 2026-09-19
Books mentioned on What It Means to Be on That Hill | Seth Wickersham
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.
Ryan Holiday discussed Be on That Hill by Seth Wickersham.
Books mentioned, in the order they came up
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Be on That Hill
Discussed“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.”
Where to get it
Other mentions in this episode (4) — ad reads, self-promotion and passing references, never counted
Passing It's Better to Be Feared
“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. His new book, Be On That Hill, is two decades of reporting and writing about athletes and coaches”
Passing American Kings
“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. His new book, Be On That Hill, is two decades of reporting and writing about athletes and coaches”
Passing Be on That Hill
“I'd be curious for you like I mean whenever I go into the office of a coach your books are in their office like what is it like being the guy that everyone turns to for wisdom”
Plugged Ego Is the Enemy
“so like it is really important I think we can deceive ourselves with our own outcomes like I've actually talked about this in the ego book like it's very common for instance like someone makes a great general and then somebody says you should run for office”