The Daily Stoic Podcast

Episode: Can You Get Inside? | The Top Books Ryan Holiday Recommends
Host: Ryan Holiday
Date: January 9, 2026

Episode Overview

In this episode, Ryan Holiday explores the theme of truly internalizing philosophy—specifically Stoicism—and how the same immersive approach applies to great books. He opens with reflections on “getting inside” Stoic texts so that their lessons become not just knowledge, but a part of who we are. Ryan then pivots to a wide-ranging, passionate discussion of his all-time favorite book recommendations across genres, offering insights, anecdotes, and the reasons each book has stayed with him.

Key Discussion Points & Insights

The Importance of Absorbing Stoic Wisdom

• [00:05–03:46]
  • Ryan illustrates that significant figures—including the Stoics themselves—would revisit foundational texts constantly until they became part of their thinking.
  • He draws parallels to musicians making songs their own, referencing Johnny Cash, Luke Combs, and Phoebe Bridgers:

    "I have this thing where I listen to songs over and over again if I like them a lot...then I have to play this. It's an extra level...I have to get inside it.” (Phoebe Bridgers, cited by Ryan, [01:24])

  • Marcus Aurelius is contrasted:

    "Marcus Aurelius wrote about how the philosopher is one with their weapon, like a boxer more than a swordsman...we are trying to fuse ourselves with our philosophy, to make it instinctive, inseparable from who we are.”* ([02:18])

  • Seneca’s advice to deeply digest a handful of master thinkers, rather than skimming widely, is championed:

    “Not skim, not sample, but digest, till the wisdom takes firm hold inside you and never to be dislodged.”* ([02:48])

  • The Daily Stoic book is intended as an ongoing daily practice:

    “The Stoics aren’t something you have read. They should be something you are reading always, at every age, at every area in your life. Ideally every day, just a little bit here or there.”* ([03:14])

Ryan Holiday’s Book Recommendations: A Guided Tour

• [06:52–19:04]

Books That’ll Blow Your Mind (Nonfiction, Narrative)

• Night of the Grizzlies
  • Gritty retelling of 1967 grizzly bear attacks:

    “When you read about the lead up...you realize it was inevitable...mind blowing.”* ([07:31])

• The Tiger by John Vaillant
  • Enthusiastically praised:

    “If you haven’t read it, I don’t know what you’re doing with your life.”* ([07:45])

• Marriage at Sea
  • Story of survival after a whale sinks a boat:

    “Absolutely incredible...their marriage is under strain throughout all of it.”* ([07:56])

• Stranger in the Woods & The Art Thief
  • Real-life tales of a hermit and a prolific art thief.

Iconic and Underappreciated Biographies

• The Black Count
  • Black general in Napoleon’s army, father of Dumas.
• The River of Doubt
  • Roosevelt’s harrowing expedition:

    “Mind blowing...he took a copy of Epictetus with him.”* ([08:58])

Brilliant Books with “Terrible Titles”

• Colossus of Maroussi by Henry Miller:

  “Should just be called ‘Henry Miller Travels Through Greece’…but it is this sort of rhapsodic, beautiful book.”* ([09:19])

• Invisible Man by Ralph Ellison:

  “No, this is about figuratively, an invisible man. One of the all-time great novels.”* ([09:45])

• Notes to John by Joan Didion:

  “Sounds incredibly boring, but it’s actually...one of the greatest writers...writing these letters to her husband.”* ([10:06])

Thrillers and Narrative Nonfiction Destined for Film

• Tunnel 29: Smuggling people under the Berlin Wall, supported covertly by CBS.
• The Art Thief by Michael Finkel:

  “Is an insane book that you almost cannot believe it’s happening.”* ([11:02])

• What Makes Sammy Run by Budd Schulberg:

  “One of my favorite novels. It would make a great movie.”* ([11:23])

Books Where the Title Delivers

• The Fish That Ate the Whale
• Why Fish Don’t Exist by Lulu Miller:

  “I won’t spoil what it’s about...one of the insights is that fish don’t exist.”* ([11:57])

• Forget the Alamo
• A Confederacy of Dunces: Includes the Jonathan Swift epigraph.

Stylistically Unique or Experimental Books

• Edison by Edmund Morris (a biography in reverse):

  “I’ve never read a biography like that...but it fucking works.”* ([13:14])

• 84, Charing Cross Road:

  “Some lady in New York...starts writing letters to a rare bookseller in the UK...they never actually meet, and yet somehow they strike up this...lovely friendship.”* ([13:38])

The Power of Meditations

• Meditations by Marcus Aurelius:

  “There’s never been a book like this ever, in human history...the most powerful man in the world writing private notes to himself...and yet it’s so honest and authentic and unperformative.”* ([14:43])

Notable Experiments in Perspective and Format

• Lancelot by Walker Percy (second-person perspective):

  “It starts, ‘Come into my cell. Make yourself at home.’...one of the only two good second-person novels.”* ([15:47])

• Bright Lights, Big City (second person);
  • James (retelling Huckleberry Finn from Jim’s POV):

    “Turns out he is incredibly well read and articulate, and he’s just been putting on an act. Lovely book.”* ([16:34])

• Address Unknown:
  • Epistolary novel tracing radicalization and friendship torn apart by fascism.

Celebrating Montaigne’s Essays

• The original essayist:

  “If you haven’t read Montaigne’s essays, you should. They have been a staple for more than 500 years for a reason.”* ([17:21])

Great Biographies of Women

• Clementine by Sonia Purnell (Winston Churchill’s wife):

  “Churchill would say that his greatest accomplishment was getting his wife to marry him...”* ([17:45])

• Queen Victoria by Julia Barrett
• Queen Elizabeth II

  “Read something like 4,000 pages on Queen Elizabeth II when I was writing Discipline is Destiny...but was by no means the complete story.”* ([18:24])

• Anne Frank by Melissa Müller

  “More and more people don’t know what the Holocaust was, don’t even know who Anne Frank is, and you have to read this book.”* ([18:44])

Notable Quotes

• On Internalizing Philosophy:

  "We are trying to fuse ourselves with our philosophy, to make it instant, to make it instinctive, to make it inseparable from who we are." — Ryan Holiday ([02:18])

• On the Daily Stoic Practice:

  "The Stoics aren’t something you have read. They should be something you are reading always, at every age, at every area in your life." — Ryan Holiday ([03:14])

• On Great Books with Strange Titles:

  "One rule about books is usually the better the title, the worse the book is. But there are some exceptions to this rule." — Ryan Holiday ([11:28])

• On Meditations:

  "There’s never been a book like this ever, in human history...and from this specificity comes one of the most relatable and accessible works in all of philosophy." — Ryan Holiday ([14:43])

• On Montaigne:

  "Before this, no one had written an essay before...now the idea of just riffing on a handful of topics...it’s obviously very well established because what was once transgressive became commonplace." — Ryan Holiday ([17:21])

Timestamps for Key Segments

• 00:05 — Opening meditation: Getting ‘inside’ Stoicism, making philosophy instinctive.
• 06:52 — Bookstore anecdotes and Ryan’s philosophy on recommending books.
• 07:20–14:40 — Detailed recommendations: standout narratives, nonfiction gems, and books with odd or misleading titles.
• 14:43–16:34 — Meditations and other unique narrative experiments, including second-person novels and retellings.
• 17:21–18:44 — Classic philosophical texts and remarkable biographies of women.

Memorable Moments

• Ryan’s description of visiting Charing Cross Road and discovering it had become a McDonald’s, reflecting on literary history contrasted with modern life. ([13:57])
• His candid, passionate advocacy for books he believes are underappreciated or misunderstood because of their titles, offering a peek into his personal reading philosophy.

Conclusion

This episode serves as a powerful reminder, not only of the value of immersing oneself in Stoic literature, but also the lifelong habit of returning to—and truly digesting—books that challenge, move, and sustain us. Through entertaining stories and candid endorsements, Ryan Holiday turns a straightforward book list into an invitation to live philosophically, every day.