(New York: Random House, 2012, 2016), 480
Taleb's chapter summaries on xix+, and mine are below. My full notes/underlines are in my paperback copy.
Book I: The Antifragile: An Introduction
Chapter 1: Between Damoclese and Hydra
Summary: We don't have a name for the interesting half of life, which he calls antifragility. Domain dependence has blinded us to recognizing how systems need stress and agitation.
Chapter 2: Overcompensation and Overreaction Everywhere
Summary: Abundance is harder for us to handle than scarcity (Cato), and layers of redundancy are the central risk management of natural systems.
Chapter 3: The Cat and the Washing Machine
Summary: Acute stress is good for us, and if you are actually alive something in your soul craves randomness and disorder.
Chapter 4: What Kills Me Makes Others Stronger
Summary: Parts of the system must be fragile to make the entire system fragile (let banks fail). Keep your mistakes small enough so you can survive them. We should treat ruined entrepreneurs like we do dead soldiers.
Book II: Modernity and the Denial of Antifragility
Chapter 5: The Souk and the Office Building
Summary: The two very different risk profiles of extremistan vs mediocristan: small regular volatility or the facade of stability followed by dislocations.
Chapter 6: Tell Them I Love (Some) Randomness
Summary: Taleb shows the benefits of randomness in antifragile systems (annealing, forest fires) and the greater volatility caused by denying randomness (Egypt and Saudi). He closes with a compelling definition of "modernity" as—at its core—a denial of antifragility.
Chapter 7: Naive Intervention
Summary: Taleb gives examples of over-intervention in antifragile systems and the costs ("iatrogenics") of doing so. We should leave antifragile systems alone to correct themselves and allow that signal to be heard by checking data less frequently.
Chapter 8: Prediction as a Child of Modernity
Summary: Don't forecast, focus on avoiding fragility to things you can't forecast.
Book III: A Nonpredictive View of the World
Chapter 9: Fat Tony and the Fragilistas
Summary: Nero and Fat Tony are antifragile by betting against fragility.
Chapter 10: Seneca's Upside and Downside
Summary: Antifragility is when you have more to gain than lose. Seneca demonstrated this in his mental write-off of losses.
Chapter 11: Never Marry the Rock Star
Summary: Taleb introduces the barbell (bimodal) strategy of removing all risk possible in areas to cap downside and then taking speculative risk in others for upside. Robust to negative Black Swans and antifragile to positive Black Swans. Also the concept of path-dependence, i.e. you can't separate economic growth from risk of recession.
Book IV: Optionality, Technology, and the Intelligence of Antifragility
Chapter 12: Thales' Sweet Grapes
Summary: The option—the right but not obligation—is the way to achieve asymmetry and antifragility. Optionality achieves what we can't by knowledge or forecasting.
Chapter 13: Lecturing Birds on How to Fly
Summary: Taleb uses the example of wheels on suitcases to show that randomness is needed for both invention and implementation. He then uses the example of lecturing to birds to show how delusional we are about causality in these cases of epiphenomena.
Chapter 14: When Two Things Are Not the "Same Thing"
Summary: "Fooled by Randomness" of conflating associative vs causal, and how too much "education" doesn't actually make us smarter.
Chapter 15: History Written by the Losers
Summary: Taleb argues that theories lead to practice (not the other way around) and that overly theoretical work can lead to fragility. He demonstrates how the antifragile (right-skewed) underestimates and fragile (left-skewed) overestimates.
Chapter 16: A Lesson in Disorder
Summary: Taleb gives an autobiographical sketch of his learning to show the weakness of structured learning and the benefits of an autodidactic approach.
Chapter 17: Fat Tony Debates Socrates
Summary: Nietzsche's insight that the "unintelligible is not necessarily unintelligent" as a recognition of antifragility. Textbook "knowledge" (a la Socrates) misses a dimension: real decisions are based on risk and reward.
Book v: The Nonlinear and the Nonlinear
Chapter 18: On the Difference Between a Large Stone and a Thousand Pebbles
Summary: Fragility is graphically represented by concavity where non-linear effects compound downside. Efficiency causes fragility which is always worse the larger you are.
Chapter 19: The Philosopher's Stone and Its Inverse
Summary: We can measure the antifragility of models by measuring the impact of change in assumptions (second order effects). If you have favorable asymmetries it will pay off in the long run.
Book VI: Via Negativa
Chapter 20: Time and Fragility
Summary: Taleb observes how older things are more antifragile than new ones and likely to be around (Lindy Effect). He opposes "neomania" or the love of the new for its own sake. So...read old books, learn from history, and you can bet technologies that have been around for a long time are more likely to be around in the future.
Chapter 21: Medicine, Convexity, and Opacity
Summary: Taleb discusses convexity effects & iatrogenics in medicine. Discussion of how we are suckers for theory, but should instead act like we don't have the full story.
Chapter 22: To Live Long, but Not Too Long
Summary: Taleb shows how we are antifragile to variability in our food, showing the wisdom of religious fasting. And we are not made to live forever.
Book VII: The Ethics of Fragility and Antifragility
Chapter 23: Skin in the Game: Antifragility and Optionality at the Expense of Others
Summary: Taleb identifies the transfer of fragility as the worst part of modernity, where some get all the upside with no skin in the game and society gets the downside. People need to have skin in the game and take the consequences of their forecasts and we need to build more redundancy into systems. Your portfolio should match what you say. And the danger of capitalism is the manager agency problem.
Chapter 24: Fitting Ethics to a Profession
Summary: Taleb shows how proximity for comparison leads to the treadmill effect and shame serves as a valuable disciplinary function in small communities. He proposes a rule of not trusting those who stand to gain from their arguments and making them share in the downside of their audience. He also shows how big data leads to more cherry-picking in science and increasingly can only really be used to disprove rather than prove.
Chapter 25: Conclusion
Summary: Everything gains or loses from volatility. Fragility is what loses from volatility and uncertainty.