Why Smart People Make Bad Decisions | Ryan Holiday
Finding Mastery with Dr. Michael Gervais
January 28, 2026
What does it mean to live wisely in a loud, distracted, and often reactive world? Ryan Holiday—bestselling author and modern Stoic philosopher—returns to explore how wisdom actually works… not as a theory or a prize of age, but as a daily practice of reflection, humility, and courage.
Speakers Michael Gervais, Ryan Holiday
TopicsSelf-ImprovementEducationHealth & FitnessMental Health
Michael Gervais (0:00)
In a few short days, the brightest lights in American football will be on. Most people will see what happens on the field, but the real game, that happens in the mind. I'm Dr. Michael Gervais, and I'm teaming up again with Fox Sports Analyst and NFL Pro Bowler, Greg Olson, for a special five episode series called Game Inside the Games. We're recording from Radio Road during Championship Week, and these are shorter daily episodes that are dropping Wednesday, February 4th through Sunday, February 8th. Each episode pulls back the curtain on how elite performers prepare, how they think, and the psychological skills that they rely on to perform at their best when the world is watching. And whether you're leading a team, building your craft, or competing or parenting, or simply trying to live with more intention, these are tools you can use right away. Game Inside the Games is presented by Microsoft Co-Pilot, your AI assistant for work, and CDW. Make amazing happen. Subscribe to Finding Mastery wherever you get your podcasts, and join us February 4th through the 8th for Game Inside the Games.
Ryan Holiday (1:01)
Wisdom is not one thing but several things. Obviously, intelligence, insight, experience, understanding, its creativity, its perspective, it's all these things and more, but it is not something you were born with.
Michael Gervais (1:16)
What does it mean to live wisely in a loud, distracted, and often reactive world?
Ryan Holiday (1:21)
To me, what wisdom is, is like knowing what's what. You got to know what is and isn't, what matters, what doesn't matter. The reason I think wisdom matters is that all the other virtues are, in some ways, born from it or informed by it.
Michael Gervais (1:35)
Welcome back or welcome to the Finding Mastery podcast, where we dive into the minds of the world's greatest thinkers and doers. I am your host, Dr. Michael Gervais, by trade and training a high-performance psychologist. The idea behind these conversations is simple. It's to sit with the extraordinaries and to learn, to really learn how they work from the inside out. Today's conversation is with Ryan Holiday, best-selling author and one of the most thoughtful modern interpreters of Stoic philosophy. Ryan doesn't treat wisdom as an abstract idea or a badge that you earn. He treats it as a daily practice.
Ryan Holiday (2:07)
Life is constantly teaching you, and you are constantly being exposed to all sorts of information and ideas, and in some cases, like real truths about the human experience. And what are we doing with the information? Are we actually translating that into some kind of practical understanding and wisdom? That, to me, is what it's all about.
Michael Gervais (2:25)
Ryan breaks down the four dimensions of wisdom and why parenting may be the hardest job you'll ever do without a manual.
Ryan Holiday (2:31)
The idea that you're just like, well, this worked for my parents, and I'm not totally screwed up. I hate that sort of uncuriosity or certainty of like, well, it didn't screw me up. It's like a screwed up person about to screw up another person.
Michael Gervais (2:44)
As you listen, consider what might change if you treated wisdom not as something that you have, but something that you practice again and again. With that, let's jump into this week's conversation with Ryan Holiday. The chance to be able to sit down with you. And for those that haven't listened to the multiple conversations we've had before, for me, this is like it's, I'm on a learning curve with you, and I really appreciate the path that you've traveled ahead to bring back some of the sweetest berries and sometimes the sourest berries that you can find to say, hey, listen, this is what I've been paying attention to. So thank you again for doing the hard work and then come and celebrate here with us.
Ryan Holiday (3:29)
Well, I'm excited. I came prepared to be mentally exhausted, which is what I remember the first time I came down here and saw you. I was like, did I just do like a two and a half hour therapy session? Like, was that an interview or did I, or did I just get examined? I don't know if I remember.
Michael Gervais (3:46)
What was that like? I remember we were going.
Ryan Holiday (3:48)
Yeah.
Michael Gervais (3:48)
Like that was, I think maybe our first conversation.
Ryan Holiday (3:51)
It was. I think I was still just working out a lot of stuff. You were probably just asking me totally interview questions and I was like, like there's a famous Mitch Hedberg joke where he talks about, he went to a radio interview and they said, so who are you? And then he didn't know if he meant, he didn't know if it meant that he came to the wrong studio or if it was an existential question. And it's like, you never know.
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