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

Modern Wisdom

10/02/25

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112m

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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...

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

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

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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: ⁠⁠⁠lnkfi.re/SN-Goggins⁠⁠⁠

#712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: ⁠⁠⁠lnkfi.re/SN-Peterson⁠⁠⁠

#700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: ⁠⁠⁠lnkfi.re/SN-Huberman⁠⁠

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

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Previous Episode

The Art of Living a Courageous Life - Matthew McConaughey - #1000

September 29, 2025

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118m

Matthew McConaughey is an Academy Award-winning actor, producer and an author.

Expect to learn why Matthew says life often “rhymes”, why it’s okay if you do everything right and still not get the result you want, how Matthew views the role courage plays in his life, how to learn to deal with failure, the difference between a nice guy and a good man, the most important principle Matthew refuses to compromise on, the appropriate balance of running toward a life you want vs. away from one that you fear, how to balance self-confidence with humility, the difference between “being” and “acting”, what it means to be more impressed with the wow instead of the how, rumors on Matthew’s return to the True Detective franchise, and much more...

Timestamps:

(0:00) What It Means When Life “Rhymes”

(9:34) How Forgiving Betrayal Can Free You

(20:32) Hope, Faith, and How To Become Your Own Hero

(25:47) This Approach to Success is Everything

(31:57) The Mindset That Will Change Your Outlook on Life

(41:11) How To Find Significance in the Noise

(53:30) The Power of Courage and Conviction

(01:00:31) How To Find Balance Between Life and Work

(01:10:31) The Difference Between a Nice Guy and a Good Man

(01:17:17) Principles Matthew Refuses To Compromise On

(01:29:15) Why We Need to Stop Cancelling Men

(01:34:31) Why Living Better Outweighs Living Longer

(01:40:55) How to Build Confidence

(01:47:10) How to Stop Worrying & Trust the Process

(01:52:16) On the Road with Matthew

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 a Free Sample Pack of LMNT’s most popular flavours with your first purchase at https://drinklmnt.com/modernwisdom

Get $100 off the best bloodwork analysis in America at https://functionhealth.com/modernwisdom

Get 35% off your first subscription on the best supplements from Momentous at https://livemomentous.com/modernwisdom

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: ⁠⁠⁠lnkfi.re/SN-Goggins⁠⁠⁠

#712 - Dr Jordan Peterson - How To Destroy Your Negative Beliefs: ⁠⁠⁠lnkfi.re/SN-Peterson⁠⁠⁠

#700 - Dr Andrew Huberman - The Secret Tools To Hack Your Brain: ⁠⁠⁠lnkfi.re/SN-Huberman⁠⁠

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

Next Episode

Political Violence & The Lunatics of Your Own Side - Andrew Doyle - #1002

October 4, 2025

•

153m

Andrew Doyle is Titania McGrath, host of GB News, a comedian and a writer.

The world has shifted dramatically over the past few years, and the pace of change has only accelerated in recent months. Ideas that once lived outside the mainstream have quickly entered the Overton Window, while others have been pushed out. So what does the future hold for “woke”? Is it fading, primed for a resurgence, or simply mutating into the next cultural battleground? And more importantly, what new culture war is waiting just over the horizon?

Timestamps:

(0:00) Are Liberals Becoming More Violent?

(9:42) Why Out-of-Context Clips are So Damaging

(14:44) Was Charlie Kirk a Future President?

(18:50) Wokeness is Dying

(35:28) The Dangers of Pushing Too Hard

(45:40) Andrew’s Stance on the Wokeness

(55:22) Does Environmentalism Fit into the Woke Movement?

(01:00:48) The Woke Movement is Homophobic

(01:16:09) Why Queers for Palestine is So Juxtaposing

(01:22:41) Authoritarianism in the UK

(01:36:18) The Attack on Free Speech