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In this conversation, Michael and Caleb discuss Ryan Holiday’s book The Obstacle is the Way. They cover the good, bad, and provocative.

Both argue that it’s practically inspiring even if philosophically shallow. Michael argues that in a real sense, it’s not a Stoic book. Caleb pushes back.

(05:30) Protreptic Philosophy

(11:44) The Necessity of Popularization

(14:35) Stoicism as An Operating System

(19:00) Motivational Power

(22:01) Shallow Stoicism

(31:16) Holiday Didn't Understand Stoicism

(33:32) Muddling Through Stoic Theory

(41:38) The Cognitive Theory of Emotions

(47:03) The Spiritual Aspect of Stoicism

(48:54) 3 Disciplines

(53:43) Meditations 5 20

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Thanks to Michael Levy for graciously letting us use his music in the conversations.