Some of Nassim N. Taleb’s books have been classified as the “most influential books of the past 70 years”. You might have heard about “The Black Swan”. However, he has written other four books where he develops several important ideas as those of [Antifragility] and [Skin in the Game].

Why is it a good idea to have his books in your library? Because they offer practical insights and timeless wisdom that are valuable not just in the business and scientific fields, but also in our personal lives.

From my perspective, his main contributions relate to:

  1. The depth and broadness of his thinking: he takes us into a fascinating, and sometimes rough, trip spanning ideas from philosophy, science, business, psychology, literature, history, and more. This would be uncommon among other thought leaders and challenges the narrow world view that persists in the “techie” ecosystem;
  2. The awareness he brings about those things that we often disregard simply because of lack of evidence and which, ultimately, tend to hurt us the most. This is something fundamental to understand for those of us in analytics fields where it has become almost a mandate to base our conclusions “on evidence” discounting what is unknown. Nassim shows that preparing for the unknown is what makes systems and organizations strong;
  3. His assertion that by injecting greater uncertainty in our lives, by taking greater risks, we actually are better prepared to face the growing complexity of our world.

 
He organized his five books into an Incerto, which stands for the word uncertain revealing the core idea explored through all of the five books: “the exploration of everything we know about what we don’t know”.

The first two books, “Fooled by Randomness” (FBR) and “The Black Swan” (TBS), are considered by Nassim as introductory and theoretical books where he sets the foundation for his later book Antifragile. In FBR he describes how we tend to assign much weight to things or events that in most cases are the result of pure random behavior. In TBS he focuses on explaining those events that are rare, unpredictable and have severe consequences. The main goal of these two books in words of Nassim himself are: (1) To make it clear that human history is full of black swans and (2) that we usually don’t understand how much uncertainty is present around us and, by consequence, we interpret reality in foolish ways.

In Antifragile, he extends these two concepts and explains how organic systems are in essence antifragile systems. Antifragility, in contrast to the widely spread concept of “resiliance”, implies not only being able to rebound but also to learn and grow from past mistakes. He talks about how antifragility allows us to better navigate chaos and uncertainty and how modernity has deprived us in many ways from opportunities to become more antifragile. He praises the “boring” professions (cab drivers, prostitutes) and mocks corporate jobs and culture.

In Skin in the Game Nassim talks about the basic ethics that make life worth living and which unfortunately have increasingly been lacking in our modern societies where we prefer stability and comfort rather than brutal honesty (which leads to living in the margins of society but in peace with ourselves).

 
I recommend reading the Incerto starting with Skin in the Game because it is very practical and, almost certainly, will provide the incentive to read the other books. After this, if you want to follow a logical progression, read FBR and then TBS because, as I said, they will give the foundation to later read Antifragile, his most important work. But, if you want to go straight to the core of Nassim’s ideas and have a basic grasp of the concepts of randomness and black swans (somehow covered in SIG) read Antifragile right away where he also briefly touches upon those two concepts. If you are a data scientist, or directly work in the interpretation of data, spending time reading FBR and TBS will help you question traditional quantitative approaches and see them under a different light.

The Bed of Procrustes, integrates a variety of Aphorisms many of which are mentioned throughout his previous work. It’s an enjoyable read on its own, but its full meaning becomes more apparent after you’ve read the other books.

 
In addition to the Incerto, Taleb has written a technical book “Statistical Consequences of Fat Tails” where he describes statistical distributions that can lead to extreme events and how to use them for both statistic inference and decision making.

 
Moreover, in his mini MOOC YouTube series he debriefs some of the key concepts covered elsewhere. Here is the list of topics included:

Series Topic
1 The concept of standard deviation
2 Intro to fat tails
3 Law of large numbers
4 Central limit theorem
5 Correlation
6 Spurious metrics
7 P-values & p- value hacking
8a Power of laws
8b Power of laws 2
9 Particularizing the general
10 Sympson’s paradox
11 Path dependance
11b Drawdown & logs
12 Risk of vaccines
13 Claims of drop in violence is not statiscal
13b Power of laws & compact suppor
14 Fragility, convexity & antifragility
15 Condition vs unconditional correlation