Ryan Holiday

550: Why Smart People Make Bad Decisions | Ryan Holiday

What does it mean to live wisely in a loud, distracted, and often reactive world?

On today’s episode, bestselling author and modern Stoic thinker Ryan Holiday returns for his fourth appearance on Finding Mastery. Ryan has spent his career studying the timeless lessons of Stoicism and translating them for modern life. I always love Ryan’s insights. In this conversation, we explore why wisdom isn’t something you acquire with age — it’s something you practice every day through attention, humility, and the courage to reflect rather than react.

We examine the four dimensions of wisdom, what it means to raise children wisely in an age of noise and ego, and why courage and discernment are essential in a world of endless information and powerful technology. 

Ryan also opens up about the moral weight of leadership, how to stay grounded in truth amid political division, and why philosophy is only valuable if it’s lived.

Takeaways:

  • Why wisdom is a verb, not a noun — something you do, not something you have
  • How to practice reflection and discernment in a world built on reaction
  • What Stoicism teaches about parenting, leadership, and moral courage
  • Why courage, discipline, justice, and wisdom are inseparable virtues
  • How to stay grounded when modern life rewards speed, noise, and certainty
  • The key to staying human — and kind — in inhuman times

This conversation goes beyond ideas — it’s about living wisely when life feels anything but quiet.

“Wisdom is a verb and not a noun.”


Resources + Links

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