BONUS | Ryan Holiday's Best Book Recommendations for Dr. Becky Kennedy

Summary

The Daily Stoic: BONUS | Ryan Holiday's Best Book Recommendations for Dr. Becky Kennedy

Date: July 14, 2026
Host: Ryan Holiday (Daily Stoic)
Guests: Dr. Becky Kennedy, others

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Episode Overview

In this special bonus episode, Ryan Holiday sits down with Dr. Becky Kennedy to exchange book recommendations—particularly those related to parenting, personal growth, and the subtle art of navigating family dynamics. The discussion explores unconventional parenting books, transformative novels, and memorable biographical stories that touch on Stoic philosophy and the human experience. The tone is conversational, enthusiastic, and full of practical wisdom for readers, parents, and lifelong learners.

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Key Discussion Points & Book Recommendations

1. Unexpected Parenting Books (02:41 – 04:57)

• Dr. Becky Kennedy’s Favorites:

  • Emily Oster’s books (data-driven approach to parenting)
  • Adult Children of Emotionally Immature Parents (“Such a crazy book because it was like basically self-published and just became this sort of word of mouth, enormous book.” – Ryan Holiday, 02:50)
  • Books by Evrodsky, Siblings Without Rivalry, How to Talk So Kids Will Listen and Listen So Kids Will Talk

• Ryan’s Highlight:

  • Kafka’s Letter to His Father
    • “Kafka had a difficult relationship with his father…He writes this letter and he gives it to his mom and she of course doesn’t give it to the dad, which gives you an insight into the family dynamic…It's beautiful.” (Ryan Holiday, 03:09)
  • The Road by Cormac McCarthy
    • Not typically labeled as a parenting book but deeply evocative of the parent-child bond and the pursuit of goodness in a chaotic world.
    • “The famous image in the book is…‘we’re carrying the fire.’ And the fire is goodness.” (Ryan Holiday, 04:04)

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2. Novels That Illuminate Parenting and Growth (04:57 – 07:13)

• John Green’s The Anthropocene Reviewed

  • Ryan calls it “an incredible book,” prized for its sincerity and unique perspective—written against the grain of publisher expectations. (05:05)

• The Wedding People

  • Dr. Becky: “The last book I couldn’t put down that was fiction is The Wedding People. I love the characters. I was sad to see them go at the end.” (05:36)
  • Reminded the group of Where’d You Go, Bernadette?, for its page-turner quality.

• Memoirs of Hadrian (Marguerite Yourcenar)

  • Recommended by Ryan; a novel written as Emperor Hadrian prepares Marcus Aurelius for leadership, tying in Stoic themes of mentorship.

• Raising a Wild Hare (possibly Raising Hare or Wild Hare, discussed during 06:26–07:13)

  • Story of moving to London countryside, raising a baby wild hare (leveret).
  • “It's all about doing. It's very good.” (Ryan Holiday, 07:14)

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3. Short and Powerful Reflections (07:13 – 09:39)

• Claire Keegan’s Small Things Like These

  • “A nice little short one. Incredible.” (Ryan Holiday, 07:30)

• Totto-chan: The Little Girl at the Window (Tetsuko Kuroyanagi)

  • Hugely popular in Japan; tells of a creative, misunderstood child who finally finds a school that fits her spirit.
  • “It's like it captures what it is to be that kind of kid. It gives you a lot of sympathy.” (Ryan Holiday, 08:46)
  • “If I couldn't get somebody to read a parenting book, this is the book.” (Guest 2, 10:15)

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4. Family Stories & Challenging Fiction (09:39 – 10:27)

• Wilder Shores / Wild Dark Shores (Title uncertain, discussed as books about single fatherhood, family tragedy, and resilience.)

  • Explores family dynamics, single parenting, and grief.

• Stories involving family tragedy

  • Discussion of books where a child dies and family dynamics are deeply explored. “There's so many parenting lessons.” (Guest 1, 10:13)

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5. Sports Biographies & Leadership (10:47 – 12:22)

• What Makes Maddy Run (Kate Fagan)

  • Ryan: “I give it to all the coaches that come in. It's about this like all-American cross country athlete [who] commits suicide. And it's like, what happens? Why? What did everyone miss?... It's very haunting but powerful.” (10:48–11:16)

• Chris Bosh’s Letters to a Young Athlete

  • Recommended for young readers and sports fans. “Do that one.” (Ryan Holiday, 11:31)

• Book by Ryan’s mentor (Nike & Civil Rights figure)

  • Anecdote about a mentor who gave MLK’s speech back to him and later encouraged Michael Jordan to sign with Nike. “He owned the ‘I have a dream’ speech.” (Ryan Holiday, 12:05)

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6. On Curation and Recommendations (10:27 – 12:23)

• “The idea of the bookstore is it’s only our favorite books. So a typical bookstore of this size would have a lot more titles than we have. These are just ones that we really love.” (Ryan Holiday, 10:34)

• Ryan’s Monthly Reading List:

  • “If you want more book recommendations, I send these out in my reading List newsletter, which I’ve sent out every month for 15 years. And you can sign up at ryanholiday.net/ReadingList.” (12:23)

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Notable Quotes & Memorable Moments

• “Kafka had a difficult relationship with his father… it's a beautiful book because he's such a great writer and he just really captures like that sort of when there isn’t that parent child fit, like when the personalities don't line up and how tough that is for both parties.” — Ryan Holiday (03:09)
• “The famous image in the book is… ‘we’re carrying the fire.’ And the fire is goodness. Like in this world where people are eating each other and killing each other, and it's like the parent’s job is to help them, that they're one of the good guys and they're carrying the fire. It's beautiful.” — Ryan Holiday (04:04)
• “It's hard for an adult to write a book about what it was like to be them as a kid and somehow miraculously does that. It captures what it is to be that kind of kid.” — Ryan Holiday on Totto-chan (08:46)
• “If I couldn't get somebody to read a parenting book, this is the book that would have [them].” — Guest 2 (10:15)
• “We try to find books like... where we’re like, oh, you would love this, and you’ve not heard of it.” — Ryan Holiday (09:10)
• “[What Makes Maddy Run] is a... haunting but powerful [read].” — Ryan Holiday (11:16)

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Timestamps for Key Segments

• 02:41 – Parenting book recommendations begin
• 03:09 – Kafka’s Letter to His Father
• 04:04 – The Road and “carrying the fire”
• 05:05 – The Anthropocene Reviewed by John Green
• 05:36 – The Wedding People & Where’d You Go, Bernadette?
• 06:26 – Memoirs of Hadrian and Raising Hare
• 07:30 – Claire Keegan and Small Things Like These
• 08:01 – Totto-chan: The Little Girl at the Window
• 10:13 – Books about tough family dynamics
• 10:34 – Ryan on personal curation at the bookstore
• 10:48 – What Makes Maddy Run
• 11:23 – Chris Bosh’s Letters to a Young Athlete
• 12:05 – Mentor anecdote: Nike, MLK, and Michael Jordan
• 12:23 – Ryan’s monthly reading list newsletter

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Episode Summary

This lively, informal “book club” session between Ryan Holiday and Dr. Becky Kennedy delivers heartfelt, unconventional, and deeply personal book recommendations. The books traverse genres—nonfiction parenting guides, tragic sports biographies, evocative literary fiction—all united by themes of personal growth, family, resilience, and the Stoic virtues. Both popular and under-the-radar titles are spotlighted, offering a goldmine of reading inspiration for parents and seekers alike.

If you’re searching for books that deepen empathy, examine family ties, or illuminate the path of character-building adversity, this episode delivers with warmth, candor, and a spirit of genuine discovery.

Transcript

[Host]

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[Ryan Holiday]

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[Host]

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[Ryan Holiday]

Other than yours, do you have any favorite paragraphs?

[Guest 1]

Oh my goodness. I mean, I'm looking at these, you know. I love Emily Oster. I love adult children of emotionally immature parents. She's come to.

[Ryan Holiday]

She's amazing. That's such a crazy book because it was like basically self published and just became this sort of word of mouth, enormous book.

[Guest 1]

Evrodsky is a friend and I love her work. I love siblings without rivalry and how to talk to your, you know, how to talk to your kids Will listen Listen to your Listen to your kids. Will talk.

[Ryan Holiday]

Have you read this one?

[Guest 1]

No.

[Ryan Holiday]

So Kafka had a difficult relationship with his father. He's an artistic kid. His father's this businessman. They never got along. Towards the end of his life he writes this letter where he sort of lays it out. I sort of compare it to like family day at rehab where you finally talk about all the shit that you weren't that are secrets. And he writes this letter and he gives it to his mom and she of course doesn't give it to the dad, which gives you an insight into the family dynamic. But it's like, it's a beautiful book because he's such a great writer and he just really captures like that sort of when there isn't that parent child fit, like when the personalities don't line up and how tough that is for both parties. It's beautiful.

[Guest 1]

Oh, great.

[Ryan Holiday]

Thank you. Oh, she's, she's been here. I think about like, what are parenting books that like people don't think of as parenting books? Like the Road. Have you read the Road?

[Guest 1]

No.

[Ryan Holiday]

You've never read the Road?

[Advertiser Voice]

No.

[Guest 1]

I'm embarrassed.

[Ryan Holiday]

Now this, this. It's different once you have kids. But it's a father and a son at sort of the end of the world. And he's just trying, he's desperately trying to get his nine year old to the coast. Everything's falling apart. He doesn't know. He has no plan, just trying to get them away and all this stuff along the way. It's heartbreaking and beautiful. The famous image in the book is. And a kid repeats it to me. He's like, we're carrying the fire. And the fire is goodness. Like in this world where people are eating each other and killing each other. And it's like the parents job is to help them, that they're one of the good guys and they're carrying the fire. It's beautiful. So I think, I like that. I love this I give this book

[Guest 2]

to a lot of people, too.

[Ryan Holiday]

I don't know if you read that. I haven't yet, because that's what I think. We're trying to. We're trying to raise outdoor kids, definitely.

[Host]

All right, so that's.

[Ryan Holiday]

That's parenting.

[Guest 2]

I really like everything.

[Ryan Holiday]

Oh, my God. John Green's incredible book.

[Guest 1]

So interesting.

[Ryan Holiday]

It's like the per. Like, when somebody writes about something that, like, you could tell their publisher didn't want them to write about, and they didn't think it would have any, but they are just so obsessed with it and that only they could have written that book.

[Guest 1]

He's amazing. I'm sure you've.

[Ryan Holiday]

So good.

[Guest 1]

You've met him. He's so impressive.

[Ryan Holiday]

Actually, Savannah's who told me about your books. She's looking for a fiction recommendation.

[Advertiser Voice]

Yeah.

[Guest 1]

So nice to meet you.

[Ryan Holiday]

What kind of fiction?

[Guest 1]

You know, the last book I couldn't put down that was fiction is the Wedding People.

[Guest 2]

Oh, I love the Wedding People.

[Guest 1]

Fun. I love the characters. I was sad to see them go at the end. You know, it's over.

[Guest 2]

The main character's journey. That one really surprised me. I read the whole thing on it.

[Guest 1]

Did you? Yeah. Like, where'd you go, Bernadette? Is that what it's called? Like, back? Yeah, like, that was, like. It reminds me of that. I just didn't want to put it down. I actually have it. How did she just know? I haven't.

[Advertiser Voice]

Is it great?

[Advertiser/Promoter]

So.

[Ryan Holiday]

Yes. They have two just here. We have a sign.

[Guest 1]

Yeah.

[Ryan Holiday]

So the main character is a stoic philosopher.

[Guest 1]

Oh, man.

[Guest 2]

Okay.

[Host]

She.

[Ryan Holiday]

Yeah, she. I got a call from Oprah's people to ask me to come, and I was like, how did you hear about my stuff? And they were like, well, we just did Maria's book, and she told us about it. So she just sort of made my life up, which was very cool. New love. It's very good.

[Guest 2]

Did you give her Raising Hair?

[Ryan Holiday]

Oh, yeah. Have you read Raising Hair? No. All right, we'll do that in a second. This is another Stoic, but it's a novel. This is Memoirs of Hadrian. It's the fictional memoirs of Hadrian preparing Marcus Aurelius to be emperor, so. And he's adopted him as his son. But it's beautiful. By this French novelist. It's one of those books that, like, was famous a long time ago, and then people, sort of losses. Very beautiful. Okay. We actually have a copy of Reason here. This is. So during the pandemic, she moves to this country house in London. And she finds, like, a baby rabbit. A wild hare. Yes. It's a wild hair. You're not allowed to. But I can't pronounce the word.

[Host]

What is.

[Ryan Holiday]

Is it a leveret? I just. It's. Is it a leverette? It's a bait. She raises it. It's all about doing. It's. It's very good.

[Guest 1]

Amazing. Thank you.

[Ryan Holiday]

What do you have, Samantha?

[Guest 2]

I have small things like these, and I want them to do well.

[Ryan Holiday]

Have you. Have you read Claire Keegan?

[Advertiser/Promoter]

No.

[Ryan Holiday]

Very good. I gave her the Road. It has a similar scene in it to. To the Road, but it's very good. A nice little short one. Incredible. Thank you.

[Host]

So pretty.

[Ryan Holiday]

Any think of anything else? Oh, have you read Totochan?

[Guest 1]

Nope.

[Ryan Holiday]

Okay. We have to do Totan.

[Guest 1]

Really? Yeah. I have a lot of nose. No, Very, very poorly read. Oh, right here.

[Ryan Holiday]

Oh, okay. Oh, last one.

[Guest 1]

Wow.

[Ryan Holiday]

Okay. So Totochan, she is basically the Oprah of Japan. Okay. Like, this book sold like 10 million copies in Japan, which is like an insane number. So. But she's this little sort of precocious, creative kid in World War II era Japan. And it's about this untraditional school she goes to with this kind of like, amazing, amazing teacher. How would you describe it? Did I get it right?

[Guest 2]

I think it's a school that just beats her where she is. So they're kind of.

[Guest 1]

They.

[Guest 2]

I think she didn't feel like she fit in or find a place, and she was miserable in the situation she was in. And then she found a school that celebrated her for her, and it made her feel. I mean, it's like literally a very, very good book, I think, on par with your message.

[Ryan Holiday]

I think it's hard for an adult to write a book about what it was like to be them as a kid and somehow miraculously does that. It's like it captures what it is to be that kind of kid. It gives you a lot of sympathy for that.

[Guest 1]

What is my hit rate compared to most people? I feel like everything. I'm like, nope, haven't read that. No.

[Ryan Holiday]

No.

[Guest 2]

I don't think a lot of people have read very many of the books that were invented.

[Ryan Holiday]

We try to find books like. Like the ones where we're like, oh, you would love this, and you've not heard of it.

[Guest 1]

Oh, great, great.

[Guest 2]

But you were. Seemed like. I think because I'm familiar with your material.

[Guest 1]

Yeah.

[Guest 2]

You're easier to write my books too.

[Guest 1]

Oh, yeah.

[Guest 2]

And there's things that, like, I think that I'm. If I've read and digested your book. When I'm reading other books, if I know that there's a tie between two or for. To me something.

[Guest 1]

Yeah.

[Guest 2]

Like, I would say I didn't see them at Wild Dark Shores. That was like a. Have you read that? That is like, not that it's not a parenting book.

[Guest 1]

It is fiction. It is very much about

[Guest 2]

this, like, single dad's experience with his kids in a weird situation.

[Guest 1]

I love, I love books like that. Like, what is the book with the kid who like dies in the ice and do you know what I mean? In that pond? And it's like a whole family story. They just talk about it.

[Guest 2]

Yes.

[Guest 1]

It's by an author who wrote some other books too, but yes. Anything where there's like family dynamics. Like.

[Guest 2]

So is that the same author?

[Guest 1]

It is.

[Guest 2]

It's a Wilder Shorts?

[Guest 1]

No, I don't think so. But it's like family dynamic.

[Guest 2]

Like seeing the family dynamic.

[Guest 1]

There's so many parenting lessons.

[Guest 2]

If I couldn't get somebody to read a parenting book, this is the book

[Guest 1]

that would have Wilder Shorts.

[Guest 2]

But I also. And I was like, high school. But that's just.

[Guest 1]

I love high school. I'll see if I have. Okay, thank you.

[Guest 2]

We also really like recommending books to people.

[Guest 1]

I mean, great. I will take all the recommendations. Now I know who to text.

[Ryan Holiday]

The idea of the bookstore is it's only our favorite books. So a typical bookstore of this size would have a lot more titles than we have.

[Guest 1]

Yeah.

[Ryan Holiday]

So these are just ones that we really love. Have you read what Makes Maddie Run?

[Guest 1]

No, but I love sports stuff.

[Ryan Holiday]

This is a tragic book. I give it to all the coaches that come in. It's about this like all American cross country athlete commits suicide. And it's like, what happens? Why? What did everyone miss? What? And it's like you can see.

[Guest 1]

Start to connect the dots.

[Ryan Holiday]

You can start to connect in and then. And yeah, it's a. It's a. It's a very haunting but powerful.

[Guest 1]

My 14 year old is a pretty cool. And my 11 year old's a big, big reader. So I feel like he. And he reads a lot of. He actually gave me everything. Tuberculosis.

[Ryan Holiday]

Really?

[Guest 1]

Yeah.

[Ryan Holiday]

Okay, then he would like. Does he play sports?

[Guest 1]

Yes.

[Ryan Holiday]

Okay. This is.

[Guest 1]

Oh, amazing.

[Ryan Holiday]

Chris Bosch's. Okay. Letters to Young.

[Guest 1]

He's a basketball player.

[Ryan Holiday]

Okay, there you go.

[Advertiser/Promoter]

Do that one.

[Ryan Holiday]

Do that one. And then this. He was my mentor. I worked on this book with him. But he's the one that brought he. So he. He brings Jordan to Nike okay, so the two sort of crisscrosses of his life. He's, he's, he's on the, he's working security the march in Washington. And as Martin Luther King Jr. Walks down the stairs, he goes, Dr. King, that was an amazing speech. And he hands him the speech. And so he owned the I have a dream speech.

[Guest 1]

Wow.

[Ryan Holiday]

And then if that. So if that was the only part of his life, you'd be like, what an incredible life.

[Guest 1]

Yes.

[Ryan Holiday]

He becomes a basketball coach. He works on the 84 Olympic team, and he's the one that goes, hey, Michael, I think you should give Nike another look. And that's where that comes from. He's an incredible dude. So I think your son would like those.

[Guest 1]

Great. Thank you.

[Ryan Holiday]

If you want more book recommendations, I send these out in my reading List newsletter, which I've sent out every month for 15 years. And you can sign [e-mail] ReadingList.

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