Nassim Nicholas Taleb (2011 photo by Bloomberg via Taleb’s website


By Daniel Wilcock

A random mistake at the airport earlier this month—checking in the book I intended to read along with the bag that contained it—reintroduced me to Nassim Nicholas Taleb‘s “Incerto” series of books. Even though I’d read and loved the Black Swan a few years back, the other three volumes, Fooled by Randomness, the Bed of Procrustes, and his latest Antifragile, somehow hadn’t caught my attention despite my knowing about them. How foolish. Taleb is an intellectual of the street fighting variety. His books pull brains out of stupid mode and light them on fire. They awaken readers to errors and misperceptions everywhere. That for me is the mark of a good philosopher. Yet a grain of salt or two may be needed. His stridency and dismissiveness of others are also the marks of an egotist cult leader, which I don’t think he is, but more on that later. How did I figure that his other books weren’t worth reading? Consider this blog post a way to make amends for this error.

By good fortune, but not randomness since the book is a perennial bestseller, a bookstore at Dulles International Airport happened to have a copy of Taleb’s second edition (2005) of Fooled by Randomness. Purchase made. Thus instead of reading the third volume of Lord of the Rings on the flight to Tokyo, an equally fine endeavor, I had the pleasure of jolting my worldview a bit. In Taleb’s hands, the hours ticked by pleasantly despite the cramped conditions, bland food, and impossibility of sleep.* If you enjoy non-technical philosophy and contrarian viewpoints, I’d say give this author a try.

Each of Taleb’s books is a fractal component his larger oeuvre, which argues that the “knowledge” and advice we encounter fail to adequately take into account the random, the opaque, and the unknown. This turns most modern human beings, particularly those who pay attention to mass media, into suckers and turkeys. His focus is on how to make decisions in an environment where we are continuously deluded and blind to the big disruptions he calls “black swans.” He thinks that these big events, which we never can predict, end up running our lives. He prefers negative to positive advice. These lessons, heavily informed by ancient philosophers like the stoics and contemporary behavioral economists such as Daniel Kahneman, mostly boil down to “don’t be a fool.” This is ultimately an impossible edict for humans, but archers aim high to hit distant targets.

Fooled by Randomness is the humblest and perhaps the most endearing of Taleb’s works. It shows how he gathered the bearings of his world view and contains the key admission that contextualizes the brash and seemingly arrogant way he battles with status quo thinkers. He admits repeatedly that he is a fool himself. One thing he attacks in others is their lack of similar humility, which is risky and ultimately destructive. Without this baseline caveat, it’s easy to misinterpret as self-righteous Taleb’s attacks on most other professional thinkers, particularly financial analysts, economists, journalists, and academics.

Fooled by Randomness is Taleb’s initial takedown of professional predictors. Like all of his books, it’s a mélange of autobiography (he worked as a trader for 20 years, then as an academic who writes books and doesn’t seem to like the academy much, and now as a flâneur, which is French for an idler who lives well by not making plans), philosophy, real-world observation and fictional narrative. It introduces a semi-autobiographical character called Nero Tulip (a name suffused with wry references), a financial trader who follows a seemingly lackluster “barbell” investment strategy of bonds plus small bets that pay off big in the event of market crashes. Despite having a risk-adverse worldview, Nero envies the flashy lifestyle of his neighbor, a fellow trader getting rich quickly with the latest financial trend. The neighbor “blows up” in the end and leaves the market. Nero is vindicated and remains in the market before he randomly ends up crashing a helicopter.

Later, in the Black Swan, Taleb introduces other semi-autobiographical characters like Fat Tony, another trader (and a necktie-free wise-guy gourmand that judges people subconsciously by smelling them) who functions as a comical mirror image of the experts Taleb attacks. Despite his argument that narratives pull the wool over our eyes, he calls it the “narrative fallacy,” Taleb uses these little stories nonetheless since humans’ brains function through narratives and also because he savors their artistic side. He appreciates style and intellectual pleasure, and finds great value in novelists and thinkers whose works have withstood the erasure of time. He’s a man who since his teens has read voraciously—40 to 60 hours a week, which reminds me of the number of miles run by marathoners each week—and I think these “Incerto” books are the output of his idiosyncratic inputs.

After putting down Fooled by Randomness, I picked up both the Bed of Procrustes, and Antifragile. The former is a collection of Taleb’s aphorisms, pithy little sayings that contain his wit and wisdom, and I think best enjoyed piecemeal, perhaps a page a day. Antifragile is another beast altogether, but similar in structure and content to the Black Swan. Taleb writes that Antifragile contains his main argument, the central idea of the Incerto. The title is a new word he invented. Antifragile refers to the quality of things that benefit from randomness, volatility, damage. These things have convex shape rather than concave when plotted on an axis. They have more of an upside than a downside when stressed. Examples can include the human body (up to a certain limit), the world of small businesses, barbell-style investors, and authors. In other words, he’s come up with a philosophy based on his own path to the good life. Again, he favors negative advice, a time-tested school of thought called “via negativa.” He finds wisdom in the concept of “small is beautiful” since larger size makes things more fragile. I could go on, but if you find these ideas tantalizing, the best thing to do is pick up the original.

As promised, a grain of salt. I think any thinker who warns you off most other thinkers, and one who is so clearly impressed with his own pathways in life, runs the risk of being an egotistical cult leader. Were Taleb more of a religious fanatic, rather than what I perceive to be a very erudite and broad-minded deist, his brash denunciations of others would come across (to me) as highly suspect. He’s a rich and confident man making sweeping statements. You might argue that being a notoriously cantankerous philosopher is his retirement hobby. His words often lack much humility other than his early admission (and not often repeated by the time he gets to Antifragile) that he’s human and fooled by life just like the rest of us. I think his arguments in each book are highly worthwhile, but need to be placed in the deeper context of all four books taken together. Taleb says the books can be taken in any order, but I think Fooled by Randomness is the best place to start. Just reading the Bed of Procrustes, one might legitimately ask “who is this jackass?”

Taleb’s a self-confessed fool, but he’s grappling with the tools that illuminate his foolishness and even provide the chance for a good life. That’s why I won’t repeat the mistake of sleeping on his work. As Taleb the flâneur would argue, and as my mishap with my copy of Tolkien suggests, we gain from being open to randomness.



ANA economy-class does have a few good things going for it, such as the opportunity to savor Japanese beer such as Premium Malt’s (sic), but trans-pacific travel is still a grind. Having a good book for the 13 hour flight is an indispensable remedy for the pain of temporary captivity.

One thought on “Rediscovering Nassim Nicholas Taleb, Almost at Random

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