Notes from the Road: On Judgment and Humility
What writing 1929 — and a year of being asked to judge — taught me about hindsight, certainty, and the limits of confidence.
You start to notice patterns in the questions you’re asked.
This year, the questions — mostly about my new book 1929 — were about judgment: who failed, who should have known better, who today might be making the same mistakes. They often arrived with an expectation of clarity — clear villains, clear warnings, clear lessons.
Answering them repeatedly forced me to think harder about how easily judgment hardens into certainty.
Writing 1929 required long stretches of focus — time to sit with incomplete information, conflicting narratives, and decisions that only look obvious in retrospect. At the same time, much of the year unfolded at speed: studios, stages, airports, hotel rooms, and a steady demand to make the past legible to the present.
Living inside both experiences at once changed how I think about judgment.
I’ve spent most of my career being rewarded for decisiveness: for asking sharp questions, synthesizing information quickly, and arriving at clear conclusions. Judgment is part of the job. Measuring decisions, weighing motives, testing narratives — that’s the work.
But this year made something else clearer: our confidence in our judgments needs to be tempered by humility. It is a theme that many of the main actors in 1929 could have used more of.
We are constantly being asked to judge. Every day brings new characters and choices — people in the news now, people from nearly a century ago — all presented in formats that reward speed and certainty. The incentives push us to decide quickly who was right, who was wrong, who should have known better.
One of the most persistent traps of writing about history is hindsight. It creates the illusion that clarity was always available — that decisions were obviously misguided, that moral lines were clearly drawn, that outcomes were easy to foresee.
Some of the behavior that strikes us today as clearly immoral was, at the time, legal, normalized, and rarely interrogated. I tried repeatedly to find contemporaries who articulated objections in real-time that feel obvious to us now — objections to practices we would consider indefensible. I couldn’t find them.
That doesn’t make those practices acceptable. But it does complicate the story in ways hindsight often flattens — and it forces a more uncomfortable reckoning with how moral consensus actually forms.
After answering the same questions again and again — about what people missed, why no one stopped it, whether something similar could happen again — I began to notice that many of the questions weren’t really about history at all. They were about reassurance.
We want the past to tell us that mistakes are obvious, that bad outcomes announce themselves early, that moral failures are easy to spot from the inside. But history resists that clarity. It unfolds before anyone knows how it ends.
Judgment matters. Knowing its limits matters too.
📚 Further Reading
A few books I kept thinking about — on judgment, hindsight, and how easily certainty is wrong:
Daniel Kahneman, Thinking, Fast and Slow
On cognitive bias, overconfidence, and the limits of human judgment.
A related, less well-known but extremely valuable companion is Daniel Kahneman, Olivier Sibony & Cass Sunstein, Noise: A Flaw in Human Judgment, which focuses on why judgments vary so widely — even among experts.Philip E. Tetlock, Expert Political Judgment
An examination of how poorly confident experts predict outcomes — and why humility tends to outperform certainty over time.Barbara Tuchman, The March of Folly
A history of how intelligent societies persist in bad decisions, even when warnings are available.
(I don’t agree with all of these. That’s the point.)
🙏 A Note of Thanks
To everyone who read 1929: Inside the Greatest Crash in Wall Street History--and How It Shattered a Nation and made it a #1 New York Times bestseller — and especially to those who engaged with it seriously, critically, and thoughtfully — I’m deeply grateful for the questions, disagreements, and conversations that followed.
I’ve been especially grateful for the thoughtful reviews on Amazon and on GoodReads and the many notes and emails shared among friends, book clubs, offices, and classrooms. And thanks to the independent booksellers who have championed this book from the beginning.
As always, you can find me and my work daily in 📰 DealBook (subscribe here) and on 🎙️ Squawk Box on CNBC.
Andrew - thank you for writing this book and everything you do. As a PhD candidate researching cognitive biases and rational decision making (in the vein of Daniel Kahneman), I can't help but notice that leaders and important voices in all fields in the modern day do not exercise enough humility in their judgement. You are one of the rare exceptions, and that has been clear for many years now. Please don't stop doing what you're doing!
This lands directly on my biggest edge and my biggest weakness.
My errors don’t come from lack of judgment. They come from demanding certainty too early. From wanting the present to announce itself as right or wrong before it possibly can.
The past looks obvious only because uncertainty has been edited out of it. In real time, we are always acting with partial information, incomplete maps, and nervous systems that crave resolution.
The work, for me, is not better prediction. It’s staying regulated inside ambiguity long enough for judgment to mature, without rushing to interfere, fix, or force clarity that doesn’t yet exist.
Knowing when judgment applies, and when it doesn’t, may be the real discipline.