Ryan Holiday in Conversation with Stephanie Ruhle: Wisdom Takes Work

In a world that rewards instant reaction over reflection, outrage over understanding, and convenience over depth, how do we hold on to the values that actually make life — and society — better?

Ryan Holiday, one of the world’s bestselling living philosophers, believes that the answer lies in a virtue that feels almost endangered: wisdom. He’s not talking about a quick dose of inspiration or a clever hack; wisdom, he says, is hard and sometimes uncomfortable work. But it’s the virtue on which all the others — courage, discipline, justice — depend.

In Wisdom Takes Work, the final book in his Stoic Virtues series, Holiday draws on the lives of thinkers, leaders, and artists from Seneca to Lincoln to Joan Didion to show what it means to listen more than talk, question our own beliefs as rigorously as we question others’ and keep learning for a lifetime. In conversation with MSNBC’s Stephanie Ruhle, he’ll explore why these practices matter even more now, when attention spans are eroding, and the habits of sustained effort are slipping away.

Holiday’s appeal reaches far beyond philosophy buffs — his millions of readers and listeners include CEOs, athletes, military leaders, students, and anyone hungry for practical, timeless tools to think more clearly and live more fully. With stories that span centuries and insights you can apply today, he’ll make the case for slowing down, going deeper, and resisting the shortcuts that cheat us of real understanding.

Join us for an evening that promises not just ideas, but the kind of conversation that can change how you see the world, and how you move through it.