Discourses and Selected Writings book club questions

1. 1.

   Epictetus was a former slave who argued that a slave can be freer than an emperor. Is this claim a genuine philosophical insight about the nature of freedom, or is it a coping mechanism that serves power by discouraging resistance?

2. 2.

   The dichotomy of control is at the heart of all Stoic practice. Apply it to a difficulty in your own life right now: what is genuinely up to you, and what isn't?

3. 3.

   Epictetus says suffering comes from our judgments, not from events. Does this seem true to you — and where do you find the argument's limits?

4. 4.

   Philosophy, for Epictetus, is only real if it changes your behavior. By that measure, how philosophical is your actual daily life?

5. 5.

   The Discourses are lecture transcripts, not polished treatises — they repeat, digress, and challenge. Does this form help or hinder your engagement with the ideas?

6. 6.

   Epictetus asks his students to stop caring about reputation, property, and physical health. Is this a realistic aspiration, or does it describe something that can only be approached, never achieved?

7. 7.

   He argues you should fully commit to your social roles while remaining internally indifferent to the outcomes. What does this look like in practice — and is it different from just doing your job well?

8. 8.

   The Stoics were accused in antiquity of being emotionally cold. Does reading Epictetus give you that impression, or does his philosophy allow for a richer emotional life than it's usually credited with?

9. 9.

   How does Epictetus's Stoicism compare to more familiar varieties of resilience advice — whether from psychology, religion, or contemporary self-help? What does Stoicism offer that those don't?

10. 10.

    Epictetus says you should meet any difficulty by asking: is this up to me, or not? Try applying this to a current problem. What changes — and what doesn't?

11. 11.

    The Enchiridion is a short distillation for daily use. Many people read it repeatedly rather than once. Is there something about philosophical wisdom that requires repeated reading rather than a single encounter?

12. 12.

    Epictetus argues that all people, including the powerful, are enslaved to their desires and fears, while the person who controls their own will is free. How do you read this claim in a contemporary context of structural inequality?

How to run the discussion

• Pick six to eight, not all of them. An hour of real discussion covers fewer questions than anyone expects, and racing the list is what makes a book club feel like homework.
• Open with what people noticed, not what they concluded. Asking for a verdict first hardens opinions before anyone has heard each other.
• Let the disagreement run. The questions below that split a room are the ones worth the time; the ones everyone answers the same way can be skipped.
• Ask the quiet person a specific question. A direct, narrow question is far easier to answer than an open invitation to contribute.