As someone who read a lot growing up, I will always advise people young and old to pick up a book and not put it down until you get to the other side. I particularly like reading now because books are the one thing I can read without seeing an ad every 10 seconds.

Here are the books I wanted to share and the ones I keep going back to. Grouped by what they are useful for rather than by when I read them.

51 books, 9 subjects

Financial History and Crises

Most of what looks unprecedented has a precedent, and the precedents are usually better documented than the present.

  • Principles for Navigating Big Debt CrisesRay Dalio

    The archetype chapter is worth more than all the case studies that follow it.

  • The Ascent of MoneyNiall Ferguson

    The broad survey. A good place to start and thin exactly where the other books here are deep.

  • The Big ShortMichael Lewis

    Lewis is a storyteller first. Read it for how the trade felt, not for how it worked.

  • Devil Take the HindmostEdward Chancellor

    Speculation is not a malfunction of markets. It recurs, and it recurs with the same shape.

  • Secrets of the TempleWilliam Greider

    Seven hundred pages on the Volcker Fed and never dull. Read it before forming an opinion about what central banks actually do.

  • The Great Depression: A DiaryBenjamin Roth

    A lawyer in Youngstown writing down what the Depression looked like while it was still happening. Contemporaneous beats retrospective.

Markets and Investing

  • The Intelligent InvestorBenjamin Graham

    Chapters 8 and 20 are the book. The rest is context. Extremely slow, but valuable nonetheless.

  • The Interpretation of Financial StatementsBenjamin Graham

    Graham in 130 pages. I hand this to anyone who says they want to learn to read a 10-K.

  • The Most Important Thing, IlluminatedHoward Marks

    Second-level thinking, and the memo format taught me as much as the content did.

  • Mastering the Market CycleHoward Marks

    Where are we in the cycle and what does that imply about positioning. Marks answers it without predicting anything.

  • Fortune's FormulaWilliam Poundstone

    The Kelly criterion, Claude Shannon, and the mob. Position sizing is the part of investing almost nobody teaches, and the part I have spent the most time on since.

  • All About Asset AllocationRichard Ferri

    Unglamorous and correct. Most portfolios fail on allocation, not on selection.

  • Common Sense on Mutual FundsJohn Bogle

    Bogle on costs. The arithmetic is not arguable, which is why it is still uncomfortable.

Risk, Uncertainty, and Judgment

  • Against the GodsPeter Bernstein

    The history of how we learned to measure risk. Probability as a human invention, which is what it is. One of my favorites.

  • Fooled by RandomnessNassim Taleb

    Taleb's best book and the one he is least famous for.

  • The Black SwanNassim Taleb

    The argument is right and the tone is a lot. Both are true.

  • Thinking, Fast and SlowDaniel Kahneman

    I later learned that parts of the priming literature did not hold. Nonetheless, this book taught me how to think.

  • Your Money and Your BrainJason Zweig

    Zweig on the neuroscience of selling at the bottom. The most directly useful of the behavioral books.

  • The Psychology of MoneyMorgan Housel

    Short, and the one I give to people who do not work in finance.

Economics and Political Economy

  • Capitalism and FreedomMilton Friedman

    Friedman's case stated plainly. Worth reading in the original rather than in summary, in my opinion, including by people who disagree with it.

  • Black Rednecks and White LiberalsThomas Sowell

    Sowell arguing that cultural patterns travel and persist. Heavily contested. Worth engaging with directly rather than secondhand.

  • Why We're PolarizedEzra Klein

    A structural account of polarization rather than a moral one. It sits deliberately across the table from the two books above it.

  • Ten Global Trends Every Smart Person Should KnowBailey and Tupy

    A useful corrective when the news makes everything feel terminal.

Technology and Society

  • Zero to OnePeter Thiel

    Monopoly as the objective rather than the accusation. The chapter on competition is the one that matters.

  • The FoundersJimmy Soni

    The PayPal group before they were the PayPal group. There is a reason they are called the PayPal mafia.

  • The ShallowsNicholas Carr

    What reading online does to attention. I try to reread it whenever mine gets worse.

  • The Filter BubbleEli Pariser

    Published in 2011 and more accurate now than it was then, which is the definition of a good prediction.

  • Guns, Germs, and SteelJared Diamond

    Geography as the independent variable. Historians contest it. Still a useful frame to argue with. Referenced it a lot in college.

  • Blink, The Tipping Point, OutliersMalcolm Gladwell

    Gladwell is a stylist more than a scientist. Read for the framing and verify the studies yourself. Great reads though.

Method and Craft

  • PrinciplesRay Dalio

    Another foundational book. The management half is better than the life half though.

  • Writing That WorksRoman and Raphaelson

    Ogilvy's agency on how to write. Short, and it has improved every memo I have written since.

  • The War of ArtSteven Pressfield

    On resistance. Useful on the days the work is not getting done.

Philosophy

  • MeditationsMarcus Aurelius

    A Roman emperor's private notes on staying steady. Not written to be read, which is why it works. I think the readings should be taught in schools.

  • Man's Search for MeaningViktor Frankl

    Frankl in the camps. The clinical second half is the part people skip and should not.

  • When Breath Becomes AirPaul Kalanithi

    A neurosurgeon dying at 37, on what work is for.

  • How Will You Measure Your Life?Clayton Christensen

    Christensen applying strategy frameworks to a life. Sounds glib. Is not.

  • The Miracle of MindfulnessThich Nhat Hanh

    On attention. Quick read.

History and Biography

  • Caesar: Life of a ColossusAdrian Goldsworthy

    Caesar without the mythology. Useful on how power is actually accumulated, which is slowly and then not.

  • Natural Born HeroesChristopher McDougall

    Cretan resistance fighters and the physiology of endurance. I read it while training for an Ironman, which probably explains the affection.

Fiction

Not adjacent to the rest of this. Just what I read.

  • Blood MeridianCormac McCarthy

    The best American novel I have read and the hardest to recommend.

  • All the Pretty HorsesCormac McCarthy

    McCarthy when he is not trying to break you.

  • The RoadCormac McCarthy

  • The Sun Also RisesErnest Hemingway

    Two hundred and fifty pages of people avoiding the subject.

  • The Nine Cloud DreamKim Man-jung

  • 1984George Orwell

  • The CircleDave Eggers

    1984 for the surveillance you volunteer for.

  • The FountainheadAyn Rand

  • A Song of Ice and FireGeorge R. R. Martin

  • The Dark TowerStephen King

  • The Darkness That Comes BeforeR. Scott Bakker

  • Hell HouseRichard Matheson

Next

Recommended, queued, not yet read. This list is honest about that.

  • Manias, Panics, and CrashesCharles Kindleberger

  • Lords of FinanceLiaquat Ahamed

  • The Price of TimeEdward Chancellor

  • This Time Is DifferentReinhart and Rogoff

  • Security AnalysisGraham and Dodd

  • Expectations InvestingMauboussin and Rappaport

  • Margin of SafetySeth Klarman

  • Wages of DestructionAdam Tooze