The Question That Haunts the World’s Most Successful People | Andrew Ross Sorkin (PT. 2)

The Daily Stoic

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Education, 694393, Daily Stoic, Society & Culture, Stoic, Stoicism, Self-improvement, Business, Stoic Philosophy, Philosophy, Ryan Holiday

4.6 • 4.7K Ratings

🗓️ 6 December 2025

⏱️ 54 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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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Transcript

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