#1001 - Ryan Holiday - Stoicism’s Lessons on Becoming Wise

Modern Wisdom

Chris Williamson

Society & Culture, Health & Fitness

4.7 • 4.6K Ratings

🗓️ 2 October 2025

⏱️ 112 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Ryan Holiday is a podcaster, marketer and an author. If intelligence were enough, the smartest among us would also be the wisest. Yet time and again, they stumble over life’s simplest lessons. Wisdom isn’t about knowing more; it’s about seeing deeper. So how do we shed the illusion of being ‘smart,’ and actually grow into wisdom? Expect to learn what Ryan learned from his near-death experience, what most people get wrong about wisdom, how daily habits compound into wisdom across a lifetime, what Ryan learned from studying the Wright Brothers, why in a culture of shortcuts and “life hacks,” how Ryan convinces people that wisdom is worth the long, uncomfortable path, what a Stoic would say about when you’ve lost yourself in life, why humility is such a crucial ingredient for wisdom, and much more… Sponsors: See discounts for all the products I use and recommend: https://chriswillx.com/deals Get 5 Free Travel Packs, Free Liquid Vitamin D, and more from AG1 at https://ag1.info/modernwisdom Get $100 off the best bloodwork analysis in America at https://functionhealth.com/modernwisdom Get a Free Sample Pack of LMNT’s most popular flavours with your first purchase at https://drinklmnt.com/modernwisdom Timestamps: (0:00) Why We Need to Push Outside Our Comfort Zone (5:13) Banning Books Isn't Ethical (16:41) Does Learning Keeps Us Humble? (27:48) Why We Learn Lessons from Old Tales (33:41) Literally True, Figuratively False (50:33) Do the Work Now to Build Your Wisdom (57:55) Stoic Advice for When You’re Lost in Life (01:03:45) How Stockdale Remained Unbroken Extra Stuff: Get my free reading list of 100 books to read before you die: https://chriswillx.com/books Try my productivity energy drink Neutonic: https://neutonic.com/modernwisdom Episodes You Might Enjoy: #577 - David Goggins - This Is How To Master Your Life: https://tinyurl.com/43hv6y59 #712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: https://tinyurl.com/2rtz7avf #700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: https://tinyurl.com/3ccn5vkp - Get In Touch: Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx YouTube: https://www.youtube.com/modernwisdompodcast Email: https://chriswillx.com/contact - Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

Click on a timestamp to play from that location

0:00.0	How did the live shows go?
0:01.5	The last time we were talking, we were discussing upcoming live shows. Yeah, I think I was doing two in Australia, and you gave me this advice. You were like, well, you told me that you'd done it with no notes. And usually, like, when you do talks at events, like, they don't want you to just go up and give a speech. They want, like, a presentation. But these were, this was different. So yeah, I had to
0:21.0	figure out how to do it with no, no notes, which was, it was interesting, like, it's good to
0:28.4	pick arbitrary challenges and take something that you're good at that you've done a lot of
0:32.7	times and just figure out a way to do it the hard way. Yeah, what's new. Yeah. And so I had to sort of reinvent it from scratch. It was challenging but good. It's actually funny. In Marx's Realist's Meditations, he talks about practicing, holding the reins with your non-dominate hand. And so just like, what's the way that you're comfortable doing it? What's the way you normally do it? and then how do you force yourself to do it not the way that you like to do it? And to force yourself to do it in front
1:02.0	of the way you're not comfortable doing it in front of 2,000 people. A huge fucking audience.
1:06.0	It's a, you know, it's a whole thing. Difficulty plus. Yeah. I've always thought about doing a podcast episode with a guest that somebody had organized for me
1:15.0	and sat down opposite me and I didn't know who it was.
1:17.9	Yes.
1:18.2	And I had to try and do an episode without breaking the fourth wall that I didn't know who they were
1:23.4	and see if I could excavate what the fuck is going on here.
1:27.1	Who is this psychologist, athlete coach,
1:31.8	trying to, like, you, what the fuck are you?
1:33.5	And do it without, like, destroying the episode.
1:36.1	I always thought that would be, like, a fun challenge.
1:37.6	Well, and the reason you challenge yourself artificially
1:40.3	is that life doesn't really care about your plans.
1:44.4	It doesn't play by your rules.
1:45.4	So I had a talk I was supposed to do in Kentucky like a couple weeks ago.
1:49.7	And so I was supposed to fly in.
1:51.6	I had all day.
1:53.3	And then I would do the talk at night.
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Chris Williamson, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Chris Williamson and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.