On with Kara Swisher On with Kara Swisher

Ryan Holiday on the Case for Stoicism in an Age of Distraction

Aug 17, 2026 · 52m

Summary

Kara Swisher interviews Stoicism expert Ryan Holiday about the philosophy's modern resurgence and its misuse by tech leaders and politicians. They discuss how Stoicism emphasizes virtue and self-control rather than emotionlessness, contrasting ancient wisdom with today's hyper-individualistic culture. Holiday critiques Silicon Valley figures for perverting these principles to justify ego and excess, while exploring how the philosophy offers moral direction in chaotic times.

Topics discussed

Introduction: Rome, America, and the rise of Ryan Holiday The modern stereotype of Stoicism and its appeal to young men Defining Stoicism: The four virtues and controlling your response Discipline as self-mastery and the historical context of the Stoics Why Stoicism resonates during times of chaos and political failure The Pope, technology, and the search for moral clarity Marcus Aurelius, freedom, and the 'cashmere prisons' of billionaires The ethical contradictions of Roman emperors and modern leaders Sponsors: Built, Gruen, and Odoo Stoicism, gender, and why it attracts young men seeking emotional control Case study: Doug Cherny and the destruction of WeWork The common good vs. shareholder value and social media incentives Media responsibility and the dilemma of amplifying harmful voices Tech leaders, Elon Musk, and the 'brain-fucked' state of modern elites Political engagement, immigration, and the cost of speaking out Practical Stoicism: Maintaining decency in a broken world The decline of reading and the importance of literature and poetry The power of journaling and introspection for leaders
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