Book · 2026 · Sports & Recreation
Be on That Hill
Stories from the Summits of Sport
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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.
Ryan Holiday · The Daily Stoic · Sep 2026 What they say about it
- Explores the pursuit of greatness“pursuit of greatness”2
The best things said about it
These are all about internal struggles of people trying to achieve something.
When I was putting together 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 you know, 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 and anyone who does creative work.
There's two stories in the book that kind of deal with those moments.
Why people recommend it
Every mention
Seth Wickersham when I was putting together stories for the collection, you know, again, some of these things can sound kin… 4
Discussed
“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.”
Discussed
“when I was putting together 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.”
Discussed
“and you know, 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 and anyone who does creative work.”
Discussed
“there's two stories in the book that kind of deal with those moments the smaller one is from the AFC championship game this past year where Sean Payton goes for it on fourth and one yeah and they don't get it and that ends up being kind of the difference in the game”
Ryan Holiday His new book, Be On That Hill, is two decades of reporting and writing about athletes and coaches and that… 2
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.”
Discussed
“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”
Other mentions (1: passing, ad reads, own books)
Passing
“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”