Even the giants of history couldn’t outrun insecurity, comparison, or the feeling of not having enough. In today’s episode, Ryan continues his conversation with Andrew Ross Sorkin to talk about why success rarely feels satisfying in the way you expect, why the goalposts always seem to move, and how Andrew has seen this pattern play out in some of the wealthiest and most accomplished people in the world.

Andrew Ross Sorkin is a financial columnist for The New York Times and a co-anchor of CNBC's Squawk Box. He is also the founder and editor of DealBook, a financial news service published by The New York Times. He wrote the bestselling book Too Big to Fail and co-produced a movie adaptation of the book for HBO Films. He is also a co-creator of the Showtime series Billions. His new book is 1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation. 

You can grab signed copies of 1929 by Andrew Ross Sorkin at The Painted Porch: https://www.thepaintedporch.com/

Follow Andrew Ross Sorkin on Instagram @SorkinSays and on X @AndrewRSorkin 

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The myth of the self-made man is just that, a myth. There has never been such a thing.

🎥 Check out the Arnold Schwarzenegger episode:  https://www.youtube.com/watch?v=PBQlSMOVTAg

📚 Pick up a copy of Arnold Schwarzenegger's book Be Useful: Seven Tools For Life at The Painted Porch: https://www.thepaintedporch.com/

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It doesn’t matter how smart you are. In the moment, if you can’t control your emotions, you will be stupid.

🪙 Carry The Daily Stoic Pause & Reflect Medallion as a reminder to pause. A pause creates space. A pause creates clarity. A pause can change everything. | Grab The Daily Stoic Pause & Reflect Medallion at dailystoic.com/pause

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Power is corruptive and corrosive no matter your age. To the young and inexperienced, it is even worse.

📕 Book Mentioned: Wisdom Takes Work by Ryan Holiday

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How do you stay locked in on one project for eight years? Andrew Ross Sorkin shares what he learned while writing his bestselling book 1929: Inside the Greatest Crash in Wall Street History and How It Shattered a Nation in today’s conversation with Ryan. They talk about what it really takes to write a massive, deeply researched book while juggling a demanding career and family life. Andrew opens up about the fear, insecurity, and obsession that fueled his eight year journey into the world of 1929. Ryan and Andrew get into why writing still feels hard for him, the surprising reality of how much of history comes down to human behavior, and the strange process of trying to understand people who lived a century ago.

Andrew Ross Sorkin is a financial columnist for The New York Times and a co-anchor of CNBC's Squawk Box. He is also the founder and editor of DealBook, a financial news service published by The New York Times. He wrote the bestselling book Too Big to Fail and co-produced a movie adaptation of the book for HBO Films. He is also a co-creator of the Showtime series Billions. His new book is 1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation. 

You can grab signed copies of 1929 by Andrew Ross Sorkin at The Painted Porch: https://www.thepaintedporch.com/

Follow Andrew Ross Sorkin on Instagram @SorkinSays and on X @AndrewRSorkin 

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We have to illustrate those virtues of courage and justice toward and for and through others. To help people from going hungry. To alleviate someone’s worry and fear. To put food on their table.

Feeding America | We donated the first $30,000 and would love your help in getting to our goal of $300,000—which would provide over 3 million meals for families across the country! Just head over to dailystoic.com/feeding—every dollar provides 10 meals, even a small donation makes a big difference.

📚 Books mentioned:

On the Shortness of Life: Life Is Long If You Know How to Use It by Seneca

The Daily Stoic Journal: 366 Days of Writing and Reflection on The Art of Living by Ryan Holiday

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Let us be good Stoics today and prove that we don’t just talk about this philosophy—we live it.

Feeding America | We donated the first $30,000 and would love your help in getting to our goal of $300,000—which would provide over 3 million meals for families across the country! Just head over to dailystoic.com/feeding—every dollar provides 10 meals, even a small donation makes a big difference.

Resources Mentioned:

- Action Against Hunger: https://www.actionagainsthunger.org/

📘 Grab the hardcover edition of The Daily Stoic here: https://store.dailystoic.com/

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There’s so much happening in the world, and so much of it feels terrible. There is dysfunction. There is conflict. There is outright lawlessness. There is corruption. There is cruelty. But there’s a really easy way to feel better. 

Feeding America | We donated the first $30,000 and would love your help in getting to our goal of $300,000—which would provide over 3 million meals for families across the country! Just head over to dailystoic.com/feeding—every dollar provides 10 meals, even a small donation makes a big difference.

🎟️ Come see Ryan Holiday LIVE: https://www.dailystoiclive.com/

• Seattle, WA  - December 3, 2025 
• San Diego, CA - February 5, 2026 
• Phoenix, AZ - February 27, 2026

👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/

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 Most of what people know about Stoicism is totally wrong. They might recognize names like Marcus Aurelius or Epictetus, or they assume the whole philosophy is about being stoic in the modern sense, cold, emotionless, shut down, resigned. But that picture couldn’t be more off.

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Facing death rewires your view of the world. Today's guest, bestselling author and legendary war reporter Sebastian Junger, can explain how. In this episode, Sebastian opens up to Ryan about the sudden, freak medical emergency that nearly killed him in minutes and how that moment completely rewired the way he thinks about time, technology, fear, fatherhood, and what actually matters.

Sebastian Junger is the #1 New York Times Bestselling author of The Perfect Storm, Fire, A Death In Belmont, War, Tribe, Freedom and In My Time Of Dying.   As an award-winning journalist, a contributing editor to Vanity Fair and a special correspondent at ABC News, he has covered major international news stories around the world, and has received both a National Magazine Award and a Peabody Award. Junger is also a documentary filmmaker whose debut film "Restrepo", a feature-length documentary (co-directed with Tim Hetherington), was nominated for an Academy Award and won the Grand Jury Prize at Sundance. He is also the founder and director of Vets Town Hall.

Follow Sebastian on Instagram @SebastianJungerOfficial and on X @SebastianJunger 

📚 Grab signed copies of Sebastian’s books Tribe, Freedom and In My Time Of Dying at The Painted Porch | https://www.thepaintedporch.com

🎥 Watch Sebastian Junger's first episode on The Daily Stoic Podcast: https://www.youtube.com/watch?v=kApbOu6bXt0

🎟️ Come see Ryan Holiday LIVE: https://www.dailystoiclive.com/

• Seattle, WA  - December 3, 2025 
• San Diego, CA - February 5, 2026 
• Phoenix, AZ - February 27, 2026

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