In this episode, Caleb talks with Massimo Pigliucci about his new book, How to Be a Happy Skeptic, and the thinker at its center: Cicero. They trace skepticism from Pyrrho’s radical doubt to the Academics, who found a better path. You don’t need certainty. You need to know how sure to be, then act (or not).

The Stoics and skeptics argued for decades over whether truth leaves a mark you can trust. What happens when you admit you might be wrong?

Read How to Be a (Happy) Skeptic.

(03:00) Pyrrhonism: suspend judgment, find peace

(06:50) The Academics go back to Socrates

(08:40) Fallibilism: senses and reason both fail

(10:20) Carneades and the degrees of probability

(18:00) Skeptics versus Stoics: the cataleptic impression

(22:20) Certainty, polarization, and the case for doubt

(25:30) Cicero, friend and critic of the Stoics

(27:00) On Divination: the first book against pseudoscience

(31:40) On Ends and the gift of aporia

(37:00) Virtue, friendship, and the good life

(41:50) Seneca and skeptical Stoicism

(44:50) Cicero’s life and death

(55:40) Being useful to others

Download the Stoa app (it’s a free download): https://stoameditation.com/pod

If you try the Stoa app and find it useful, but truly cannot afford it, email us and we’ll set you up with a free account.

Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

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

https://ancientlyre.com/

Get full access to The Stoa Letter at www.stoaletter.com/subscribe