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Podcast 2020-10-08

Ryan Holiday || Lives of the Stoics

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Today it is great to have Ryan Holiday on the podcast. Holiday is one of the world’s foremost thinkers and writers on ancient philosophy and its place in everyday life. He is a sought-after speaker, strategist and the author of many bestselling books including The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph, Ego Is […]

Episode Details

Show Notes


Today it is great to have Ryan Holiday on the podcast. Holiday is one of the world’s foremost thinkers and writers on ancient philosophy and its place in everyday life. He is a sought-after speaker, strategist and the author of many bestselling books including The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph, Ego Is the Enemy, The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living , and the number one New York Times bestseller Stillness is the Key. His books have been translated into over thirty languages, and been read by over two million people. He lives outside Austin, Texas with his family, and his most recent book is Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius.

Time Stamps

[00:01:10] Stoicism and “works over words”

[00:04:04] Modern day Stoicism

[00:05:16] Knowledge for knowledge’s sake vs. practical purposes of philosophy

[00:06:58] The four virtues of Stoicism

[00:07:59] Living well versus living the good life

[00:10:04] The founding fathers and Stoicism

[00:11:18] Ryan’s writing vs. academic writing

[00:17:43] The deeply personal Meditations by Marcus Aurelius

[00:19:21] Zeno the Prophet and the founding of Stoicism

[00:20:41] Living in harmony with nature

[00:22:16] How COVID-19 has given Ryan perspective on being zoomed into life

[00:25:33] Eastern and Western conceptions of stillness

[00:29:30] The relationship between Stoicism and humor

[00:30:11] Aristo the Challenger and the influence of cynicism on Stoicism

[00:31:01] Zeno the Maintainer and the repetition of names in Roman times

[00:33:38] Antipater the Ethicist and transcending individual selfishness

[00:37:56] Panaetius the connector and Stoicism beyond virtue

[00:39:36] Women in Stoicism and Portia Cato

[00:40:58] “Cancelling” Stoicism and the tearing down of Confederate statues

[00:44:48] Posidonius the Genius and the battle between our lower urges and higher nature

[00:46:26] The omission of frivolity in Stoic writing

[00:48:16] Cato: Roman among the Romans

[00:51:58] Epictetus and the nature of freedom

[00:54:27] How Marcus Aurelius became the emperor of Rome

[00:57:13] How Ryan has grown since his earliest engagements with and writings on Stoic philosophy

Seven core insights

What 11 years of conversation
revealed

  • 01
    Being over DoingThe richness of presence and inner life over constant productivity.
  • 02
    Creativity over EfficiencyMaking space for imagination and originality in a world that prizes optimization.
  • 03
    Self-Actualization over AchievementBecoming the fullest version of yourself, not just reaching the next milestone.
  • 04
    Deep Fulfillment over HappinessPursuing meaning and depth rather than fleeting positive feelings.
  • 05
    Self-TranscendenceGoing beyond the self to serve something larger — the highest expression of human potential.
  • 06
    Meaning & CompassionThe threads that run through every great conversation — purpose, connection, and care.
  • 07
    Human PossibilityThe unwavering belief that every mind is capable of far more than we’ve been told.

About the guest

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11 years of
human possibility

478 episodes exploring creativity, intelligence, well-being, and what it means to be fully human. The archive is yours to explore.