Andrew Ross Sorkin on writing a 600-page history book across eight years

Executive overview

Writing a major history book while holding two full-time jobs requires extreme constraint over time and attention. Sorkin spent eight years researching and writing 1929: Inside the Greatest Crash in Wall Street History, working in stolen blocks — nights, airplanes, vacation beaches, tennis sidelines.

The central challenge: archival history demands a different kind of reporting. Unlike living sources, the dead don't give interviews. Everything depends on what survives in boxes.

The forcing mechanism of a constrained schedule turned out to be an advantage, not a liability.

The writing process

• Needs a minimum two-hour block; the first 30–40 minutes is ramp-up just to re-enter the work
• Writes at night, on planes (wifi off), and on vacations — anywhere with uninterrupted time
• Cannot write in open newsrooms post-pandemic; requires a closed door
• Avoids the "splatter and fix" approach — believes first-draft quality caps how good a revision can be; a C draft can never become better than a B without starting over
• Audio book recording revealed repeated words and patterns invisible during normal editing
• A publisher deadline was the only thing that stopped further revision

Research and archival reporting

• The 1929 project began on vacation after downloading books about the crash and sensing a gap worth filling
• Primary fear: not finding granular detail to make characters from 100 years ago feel real and consistent
• Used a PhD researcher to learn how to navigate archives and libraries
• Photographed tens of thousands of pages on an iPhone; built a Dropbox system to store them
• During the pandemic, paid graduate students to photograph specific archive boxes when libraries were closed
• AI was not reliable for OCR on handwritten documents — hallucination rate too high to trust
• Found crucial documents years after first encountering them, only recognizing their significance once more context had accumulated

Understanding historical characters

• It took years to understand what motivated Charlie Mitchell, the book's main character — what insecurity or gap he was trying to fill
• Spent time trying to inhabit how each person rationalized decisions that today seem illegal or immoral
• Carter Glass (architect of the Federal Reserve and Glass-Steagall) was also an active segregationist — Sorkin had to hold both truths simultaneously without collapsing the contradiction
• The key insight from David McCullough: they didn't know what was going to happen. History is always gray from inside the moment.

Schedule and time blocking

• Wakes at 4:30am, on live television by 6am, anchors three-hour show
• Spends afternoons planning, writing, editing the Dealbook newsletter (published six days a week)
• Uses time blocking extensively: calendar showed "1929" in orange for years — specific windows on weekends, afternoons, trips
• Tight schedule functioned as a Pomodoro-style forcing mechanism: two hours meant two hours, no procrastinating
• All the parallel work — TV, newsletter, the Showtime series Billions — fed each other rather than competing

On book tours and repetition

• Almost every interview on the 2025 book tour opened with the same question: are we in a bubble now?
• Giving the same answer dozens of times creates a strange phoniness — the words stop feeling like genuine thought
• Also: outfit-tracking across media appearances to avoid looking like you own one shirt

Journalism versus history

• Daily journalism is structurally incapable of the depth that books allow — it's the first draft of events, by nature a snapshot
• Reporters who cover the same beat for 20–30 years (Peter Baker, Maggie Haberman cited as examples) produce work with contextual depth that approximates historical understanding
• Most journalists rotate beats every few years — they become well-rounded but lose depth
• Books let you present the full iceberg; journalism shows only the tip