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Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
In this episode, bestselling author Ryan Holiday explores Stoicism with host Chris Hutchins, revealing how this ancient philosophy can help modern professionals focus on what truly matters. (01:06) Holiday explains that Stoicism isn't about being emotionally detached, but rather about recognizing that "we don't control the world, but we control how we respond to the world." The conversation covers practical applications of the four Stoic virtues—courage, discipline, justice, and wisdom—and how they can help us navigate everything from parenting challenges to professional setbacks. (30:13) Holiday shares personal examples of applying Stoic principles, including how he approaches book launches and success metrics, demonstrating that even experts in philosophy continue to struggle with and learn from these timeless teachings.
Ryan Holiday is a bestselling modern philosopher and author whose books on Stoic philosophy have sold over 10 million copies in 40+ languages. He has written influential works including The Daily Stoic, The Obstacle Is the Way, Ego Is the Enemy, and Stillness Is the Key. Holiday is also the founder and host of The Daily Stoic podcast, helping millions apply ancient wisdom to modern life through daily insights and practical applications.
Chris Hutchins is the host of the All The Hacks podcast, focused on helping ambitious professionals upgrade their money, points, and life. He creates content designed for high-achieving individuals looking to optimize their personal and professional decisions through actionable insights and expert interviews.
Holiday emphasizes that most people waste precious mental energy focusing on things outside their control—other people's opinions, market conditions, external outcomes—while neglecting areas where they have actual influence. (09:49) He uses his book publishing experience as an example: instead of anxiously awaiting reviews or sales numbers, he focuses on showing up daily to write and defining success by his own standards of improvement and gratitude for the work itself. This approach requires constant vigilance because, as he notes, "we spend a good chunk of that focused on the parts of it that are not up to us, and then we wonder why we don't get the things that are up to us as good as they can be."
One of the most practical Stoic techniques Holiday discusses is the concept of testing your initial impressions before reacting. (14:45) He explains how Epictetus taught that we should examine our immediate emotional reactions like skilled money changers testing coins for authenticity. When you feel insulted, angry, or disappointed, pause and ask: "Is this actually true? Is this as important as my initial reaction suggests?" Holiday shares how he applies this when evaluating external validation like awards, realizing that many prestigious recognitions are effectively purchased through expensive campaigns and decided by people he may not even respect.
Holiday reveals a crucial insight about modern information consumption: most news and social media are designed to provoke high-valence emotions, particularly anger and frustration. (39:52) He argues that real-time information isn't necessary for most people unless they're running hedge funds or seeking political office. Instead, he suggests consuming well-edited, weekly publications that provide balanced perspectives you actually pay for. The constant stream of developing stories keeps us in a perpetual state of incomplete information and emotional arousal, which serves engagement metrics but destroys peace of mind and clear thinking.
Contrary to popular belief, Holiday explains that discipline isn't always about doing more—sometimes it's about knowing when to stop. (33:54) He references Aristotle's concept of the golden mean, explaining that all virtues sit between two vices. For high-achieving individuals, the real discipline often involves turning down opportunities, taking rest days, or recognizing when optimization itself becomes counterproductive. Holiday admits his own struggle with this, noting that successful people often get rewarded for their drive, making it difficult to know when enough is enough.
Holiday challenges the common assumption that wisdom comes automatically with age and experience. (54:22) He references Churchill's observation about someone who "stumbled over the truth, quickly picked himself up and carried on as if nothing had happened." True wisdom requires intentional work: reading, seeking mentorship, teaching others, and actively reflecting on experiences. He shares the story of Zeno being told he would become wise when he learned to "have conversations with the dead"—which turned out to mean engaging with the accumulated wisdom of great thinkers through books and philosophy.