I recently finished Skin in the Game: Hidden Asymmetries in Daily Life by Nassim Nicholas Taleb. Although there were some interesting tidbits I ultimately found it disappointing. Although I haven't read all of Taleb's books, I did find Antifragile to be interesting and thought-provoking, but occasionally frustrating. Skin in the Game emphasizes the things I find aggravating about Taleb as a writer without having enough deep ideas or valuable insights to offset the negatives.

(cover image from Amazon.com)

A collection of essays

The book tells you up front that it's a collection of essays, so it reads like it moves from topic to topic rather than delivering a powerful central message. The essays all touch on some common themes about risk and probability, so it doesn't read as disjointed, but I also felt that it didn't really build to anything or develop any main points in an interesting way. The writing itself is fairly good and engaging so I found it enjoyable while I was reading it, but I can't imagine revisiting any of it in the future. One of Taleb's preferred heuristics is to use something's longevity as a proxy for its quality, since that means it has been able to survive lots of potential pitfalls, which he shortands by referencing the Lindy effect – I don't anticipate this book doing very well by that metric, in contrast to something like Antifragile which still feels relevant to me.

Taleb has a tendency to strike bold positions and call it like he sees it, and sometimes expresses that in ways that seem to contain some wisdom, such as these observations about society:

The more you have to lose, the more fragile you are. Ironically, in my debates, I've seen numerous winners of the so-called Nobel in Economics (the Riksbank Prize in Honor of Alfred Nobel) concerned about losing an argument. I noticed years ago that four of them were actually concerned that I, a nonperson and trader, publicly called them frauds. Why did they care? Well, the higher you go in that business, the more insecure you get, as losing an argument to a lesser person exposes you more than if you lose to some hotshot.

And

There is inequality and inequality.

The first is the inequality people tolerate, such as one's understanding compared to that of people deemed heroes, say, Einstein, Michelangelo, or the recluse mathematician Grisha Perelman, in comparison to whom one has no difficulty acknowledging a large surplus. This applies to entrepreneurs, artists, soldiers, heroes, the singer Bob Dylan, Socrates, the current local celebrity chef, some Roman Emperor of good repute, say, Marcus Aurelius; in short, those for whom one can naturally be a “fan.” You may like to imitate them, you may aspire to be like them, but you don't resent them.

The second is the inequality people find intolerable because the subject appears to be just a person like you, except that he has been playing the system, and getting himself into rent-seeking, acquiring privileges that are not warranted—and although he has something you would not mind having (which may include his Russian girlfriend), you cannot possibly become a fan. The latter category includes bankers, bureaucrats who get rich, former senators shilling for the evil firm Monsanto, clean-shaven chief executives who wear ties, and talking heads on television making outsized bonuses. You don't just envy them; you take umbrage at their fame, and the sight of their expensive or even semi-expensive car triggers some feeling of bitterness. They make you feel smaller.

His basic prescription for most of the problems he discusses is the titular “skin in the game”: people shouldn't be insulated from the risks and downsides associated with their course of action. With things like banking executives and government officials who never paid a price for the bad decisions that led to the financial crisis it's very easy to be sympathetic to this view.

Taleb's “most interesting man in the world” routine

What I found frustrating about Antifragile and is similarly on full display here is Taleb's self-satisfied use of his own lifestyle as an illustration of the superiority of his positions. His success as a trader is seemingly treated as a universal solvent that allows him to speak with authority while dismissing views he doesn't respect. When his target seems to deserve the scorn, such as bailed-out bank executives, that's fine. But in less clear cases, such as the ire he directs towards Steven Pinker or his anti-GMO positions, it comes across to me as cheap name-calling or self-congratulatory back-patting. Similarly, his eclectic set of interests does allow him to sprinkle lots of interesting references into his writings, but his scorn for academic rigor strikes me as resulting in this book gesturing toward some interesting ideas without ever really grappling or engaging with them in meaningful depth. He'll say things like that he disproved someone's argument via proving a mathematical theorem without giving the context or showing what the theorem is or how it applies. He treats his unorthodox approach to intellectual life as being unwilling to play the bureaucratic games that academics are enthralled to, and maybe there's some truth to that, but it seems to me that there may be more than a small element of blowhard-ism in Taleb's work that his opponents may be fully justified in opposing.

Overall conclusion

I can't really recommend this book. I think there's some virtue in Taleb's iconoclasm, but in this instance he struck me more as a know-it-all holding forth to his admirers rather than someone boldly striding into the intellectual arena. I think there's a lot of value in taking what is essentially an evolutionary approach to things – “not dead” is the only long-term metric – but I suspect that other writers with a more rigorous approach and more interest in making solid cases will do that better in other places.