The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living

What is the Stoic approach to dealing with conflict, or “haters”? Explain in detail. What are some drawbacks to the approach?

Why does Holiday want to persuade readers that philosophy should play a prominent role in their lives? Is this at odds with his insistence that philosophy should be lived rather than debated?

What is the Stoic view on wealth and success? Does Holiday make allowances for his readers’ inclination to be ambitious or materialistic? Why or why not?

Research the works that 2-3 of Holiday’s quotations come from. In what context in the original work does each appear? What effect does it have to de-contextualize Stoic philosophers the way Holiday does?

Why does Stoicism place importance on observing and managing one’s own thoughts? What are the benefits of controlling one’s thoughts, and the consequences for neglecting to do so?

Explain the Stoic view on cultivating emotional neutrality or indifference to external events. What is the expected benefit of this approach? How does it conflict with a more mainstream understanding of empathy?

Stoicism is not an ascetic philosophy, but it does advise people to strictly manage their relationship with pleasurable activities. Discuss the Stoics’ relationship with pleasure.

Holiday dismisses the idea of preaching Stoicism rather than setting an example by embodying its principles. How does this belief square with his motivations in writing this book?