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Stoa Conversations: Stoicism Applied
The Obstacle Is the Way (Episode 45)
May 23, 2023
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. They analyze the value of concrete stories, the lack of systematic philosophy in the book, and misconceptions about the concept of will in stoicism. They also explore the meaning behind the book's title and encourage listeners to embrace obstacles as opportunities.
55:41
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Quick takeaways
- Ryan Holiday's book The Obstacle Is the Way switches the order of the three disciplines of stoicism, starting with perception, then action, and finally will.
- The book does not strongly emphasize the cognitive theory of emotions, overlooking a key aspect of stoic philosophy and hindering readers in understanding and managing their emotions.
Deep dives
The Book's Structure and Order of Disciplines
Ryan Holiday switches the order of the three disciplines of stoicism, starting with perception, then action, and finally will. This differs from the traditional stoic order of desire, action, and ascent.
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