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

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Dec 6, 2025

Guest

Andrew Ross Sorkin

Andrew Ross Sorkin, a prominent financial columnist and author, shares insights into the complexities of success. He discusses how insecurity and comparison often haunt even the wealthiest, revealing that true contentment is elusive. Andrew recounts powerful historical anecdotes, from Churchill to Mark Twain, highlighting the pitfalls of fame. The conversation navigates the delicate balance between ambition and satisfaction, exploring why the quest for 'enough' remains a common struggle among high achievers.

44:41

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ADVICE

Use Small Daily Wins To Stay Productive

Block time and set small daily goals to keep momentum while writing a large project.
Mark progress by asking, "Did I move the ball forward today?"

question_answer

ANECDOTE

All-Nighter Writing Routine

Andrew Ross Sorkin described writing late nights with Diet Cokes, chips, and Corona beer to sleep.
He said the routine left him feeling "so disgusting."

insights

INSIGHT

Success Rarely Feels Like Enough

Success rarely stops the inner drive; people keep chasing the next thing.
Andrew Ross Sorkin calls this a human attempt to fill a hole that rarely gets filled by achievement.

Get the Snipd Podcast app to discover more snips from this episode

How Ryan Met Andrew and Book Context

03:09 • 1min

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Writing Habits and Procrastination

04:32 • 7min

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Author Routines and Health Tradeoffs

11:39 • 3min

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Historical Anecdotes: Churchill and Mark Twain

14:57 • 4min

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Keeping Your Bearings Among the Wealthy

18:56 • 3min

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The Question of 'Enough' and Contentment

What Satisfaction Feels Like After a Book

25:29 • 4min

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Dealing with Reviews and External Validation

29:52 • 3min

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Family, Agents, and Editing Boundaries

32:50 • 2min

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Historical Losses: Grant and the Market

35:00 • 6min

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When Success Breeds Overconfidence

40:55 • 3min

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The Peril of Cloistered Genius and Podcasts

44:15 • 4min

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Money's Margins: What Wealth Actually Buys

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In 'Right Thing, Right Now', Ryan Holiday argues for the necessity of doing what’s right, even when it isn’t easy. He draws on stories of historical figures such as Marcus Aurelius, Florence Nightingale, Jimmy Carter, Gandhi, and Frederick Douglass to illustrate the importance of justice, kindness, honesty, integrity, and loyalty. The book emphasizes that justice is not an abstract concept but a daily practice that shapes one’s character and impacts those around us. Holiday challenges readers to develop their own moral code and uphold it consistently, providing concrete steps and exercises to help incorporate these values into their lives.

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1929, Inside the Greatest Crash in History and How It Shattered a Nation

Inside the Greatest Crash in History and How It Shattered a Nation

Andrew Ross Sorkin

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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