The Daily Stoic Podcast

Episode Title: Why Andrew Ross Sorkin Spent 8 Years Chasing One Story
Host: Ryan Holiday
Guest: Andrew Ross Sorkin (financial journalist, author of 1929: Inside the Greatest Crash in Wall Street History and How It Shattered a Nation)
Date: December 3, 2025

Episode Overview

This episode features a rich conversation between host Ryan Holiday and renowned journalist/author Andrew Ross Sorkin. The focus is Sorkin's new book, 1929, a sweeping and deeply researched account of the infamous stock market crash. Sorkin discusses his eight-year journey crafting the book, the painstaking process of historical storytelling, and the personal and professional challenges involved in writing such a weighty narrative. The discussion also veers into themes of motivation, the complexity of human nature, and the mechanics of deep journalistic and historical research—all viewed through a Stoic lens.

Key Discussion Points & Insights

1. Are We in a Bubble Now? (09:30–10:16)

• Holiday opens by jokingly asking Sorkin if he thinks we're currently in a financial bubble—a question Sorkin says he is asked at every tour stop.
  • Sorkin: “Almost every time… The Cliff Notes version is, should I sell everything I own?”
  • Both agree that the repetitive nature of book tours and the fixation on present-day parallels sometimes override genuine curiosity about the historical subject itself.

2. The Challenge and Pain of Writing (12:23–14:38)

• Sorkin candidly talks about the difficulties behind writing a massive, detail-rich book while juggling several jobs.
  • Sorkin: “I find writing very hard… I am in pain as I am typing.” (12:49)
  • He shares that he requires a block of at least two hours to get into a productive writing rhythm, and compares the process to working out: the first 30–40 minutes are just ramping up. (13:16)
  • Writing happened at night, on airplanes without WiFi, and even during family vacations.

3. Falling in Love with the Material & the Fear of Failure (14:38–16:48)

• The book began as a passion project on vacation, sparked by reading widely about the 1929 crash.
  • Sorkin: “For the first couple of years, it actually did feel like a true hobby... I was just trying to figure it out.” (14:21)
• Sorkin confesses fears about failing to match the success and impact of his previous book, Too Big to Fail:
  • Sorkin: “‘Maybe it worked for lots of reasons that I wasn't always sure had to do with me...’” (15:43)
• The gravity of writing about dead historical figures and the challenge of finding adequate primary sources.

4. On Obsession, Perfectionism, and the Creative Process (17:18–21:04)

• Sorkin worked on the book for eight years, often in fits and starts, punctuated by daily job responsibilities and the pandemic.
  • Sorkin: “There were periods where I was, like, full pedal to the metal… and periods where I had to be super intense in my day job.” (17:25)
• He describes the persistent urge to tinker, even after publication:
  • Sorkin: “I could see a sort of obsessive nature to it… if I didn't have a publisher telling me, ‘we would like to publish it this fall,’ I probably would've taken even more time.” (18:43)
• The agony and satisfaction of continual revision: the urge to make every sentence and detail perfect—even retroactively.

5. Craft, Method, and the Evolution of Writing & Research (22:45–30:48)

• Sorkin and Holiday discuss the impact of writing tools (longhand, typewriters vs. computers), how the inefficiency of older methods may have forced higher-quality revision.
• Recording the audiobook revealed repetitions and flaws not noticed before:
  • Sorkin: “I found a whole bunch of things that I was not pleased with myself about. This is nobody else's fault, was my own…” (23:57)
• The importance of library research and involving assistants, especially when archives were inaccessible during the pandemic.
  • Sorkin: “I would befriend different librarians, find out what kids were allowed in the libraries… I need you to take a picture of every single page in the box.” (28:46)

6. Rituals, Routine, and Making Time for Deep Work (25:56–29:32, 42:01–43:40)

• Sorkin’s tightly organized schedule: up at 4:30 am, TV by 6, editing newsletters, writing blocks in conference rooms or at home for deep focus.
  • “I map it out… I’m a big time blocker. If you were to look at my calendar for many years, there would be a lot of 1929 in orange in boxes.” (42:25)

7. The Serendipity & Frustration of Deep Research (29:46–31:37, 35:29–38:48)

• Sorkin details stories of unearthing crucial connections months or years after initially encountering a document—sometimes realizing critical links only after reviewing material several times.
  • Sorkin: “I found myself even finding stuff three and four years later… I’d see something and go, oh, shit, yes.”
• The challenge of researching “characters” long dead, aiming to understand their motivations and contradictions.
  • Sorkin: “I was looking for those things in all the characters, but… some of those things did not reveal themselves to me for a very long time.” (35:58)
  • The importance and difficulty of empathy for historical figures whose morality is alien to modern sensibilities (e.g., Carter Glass).

8. Understanding Motivation & The Limits of Journalism (38:48–41:12)

• Holiday and Sorkin explore the limits of journalism: daily news pieces lack the depth and time necessary to unravel motivations as thoroughly as a long-form historical narrative.
  • Holiday: “There’s something about that that journalism is just fundamentally incapable of doing because of the rapidness of it. It’s the first draft of events…” (38:48)
  • Sorkin: “I do think… that having reported on this world … keyed me in to the way people like this think and the different kinds of emotional reactions that they were having.” (39:14)

9. Experience, Specialization, and Depth (41:12–42:04)

• The value of “marinating” in a specialty over decades—a vanishing model in contemporary journalism.
  • “Peter Baker…or Maggie Haberman…because they’re so steeped in it…the tip of the iceberg… But in journalism, most people go from beat to beat… It makes it harder to be super deep as a result.” (41:36–42:04)

10. Productivity, Distraction, and Focus in a Hyperconnected World (45:32–46:30)

• Sorkin describes the pull of constant communication, even while needing uninterrupted focus.
  • Sorkin: “There’s no question you’re texting people…that was the thing that would throw me the most…” (45:54)
• Weekend writing and “Do Not Disturb” features help, but self-distraction remains a major challenge.

Notable Quotes & Memorable Moments

• On Book Tours & Interviews:

  • Sorkin: “Almost every time… The Cliff Notes version is, should I sell everything I own?” (09:48)

• On Writing Pain:

  • Sorkin: “I find writing very hard… I am in pain as I am typing.” (12:50)

• On Falling in Love with History:

  • Holiday: “It’s the falling in love with a world or a time period—that’s the part that’s just for you.” (15:03)

• On Fear and Legacy:

  • Sorkin: “I was scared that I wasn’t gonna be able to find the kind of granular detail that I needed to make each character pop…” (15:16)

• On Obsession:

  • Sorkin: “I could see a sort of obsessive nature to it… if I didn’t have a publisher telling me, ‘we would like to publish it this fall,’ I probably would have taken even more time.” (18:43)

• On Historical Empathy:

  • Sorkin: “I would try to think, is there some level of empathy that I can have for them, also, sort of, given the distance of today? And then try to think, how did they rationalize and justify these things to themselves?” (37:34)

• On Motivation:

  • Sorkin: “For a very long time, I don’t think I understood what really motivated him… what was the hole he was trying to fill?” (35:32)

• On Routine:

  • Sorkin: “I’m a big time blocker... There would be a lot of 1929 in orange in boxes. And those were my boxes.” (42:54)

• On Frustrations in Research:

  • Sorkin: “I thought I even saw it, like, two years earlier… it would take me two or three days to find it.” (44:10)

Structure & Timestamps

| Segment | Key Topic | Timestamps | |-----------------------------------------|---------------------------------------------------------------|--------------| | Book Tours & Bubble Questions | The repetitive nature of interviews and present parallels | 09:30–10:16 | | Writing Challenges & Process | Pain, routine, blocks, obsession | 12:23–14:38 | | Falling In Love & Fear | Obsession with period, fear of failure | 14:38–16:48 | | Perfectionism & Continuous Revision | Obsessive editing, not letting go | 17:18–21:04 | | Research Methods & Audiobook Lessons | Tools, assistants, pandemic, tech limits | 22:45–30:48 | | Routine & Deep Work | Morning schedule, blocked time for writing | 25:56–29:32; 42:01–43:40 | | Research Serendipity | Uncovering key evidence over time | 29:46–31:37 | | Motivation & Empathy for Historical Figures | Understanding “characters,” shades of morality | 35:29–38:48 | | Limitations of Journalism | News vs. deep history, narrative depth | 38:48–41:12 | | Experience, Specialization, Depth | Journalistic expertise, longevity | 41:12–42:04 | | Productivity, Distraction, Focus | Managing interruptions, mental strategies | 45:32–46:30 |

Conclusion

This episode is a tour de force on historical research, the taxing nature of creative work, and the motivations behind digging deep into a pivotal moment in financial history. Sorkin's candor on fear, obsession, and productivity offers rare insight for writers, historians, and anyone wrestling with a long-term project.

For Further Engagement

• 1929: Inside the Greatest Crash in Wall Street History by Andrew Ross Sorkin
• Follow Andrew on Instagram (@SorkinSays) and Twitter (@andrewrsorkin)
• Find more from Daily Stoic at dailystoic.com