Although Taleb is "comically arrogant and kind of childish about his disagreements with others," here are 10 things I really appreciated about Antifragile.

1) Sometimes I overstrategize how to formulate my thoughts and I get stuck never voicing them, and then articulating them badly anyway. Part of the cause of this overstrategizing comes from fear of burning bridges and fear of being outcast. Taleb frequently does not formulate his thoughts well, but one cannot say he is not bold in stating his ideas and what he thinks of other people (“frauds” and “Fragilistas”). While his style is not a virtue itself, it’s worth taking his thigh-slapping puff-chested example for what it’s worth – a bit of encouragement. Taleb provides real life examples of this too. A Lebanese widow during the civil war had her windows shot out in a fire fight. The next day she went outside and confronted the enemy soldiers. Tiny, dressed in black, guns pointing at her, she nonetheless yelled at these 20 year old boys that they were messing up the neighborhood, behaving improperly and shamefully. Taleb says it was clear that although they had guns, their faces betrayed embarrassment. This incident of a widow’s heedless self-respect reminds me also of the few resistors of arrest and interrogation Solzhenitzen mentions in Gulag Archipelago (get the unabridged edition BTW, the abridged is missing important elements of the literary experiment). Why were they able to resist arrest and interrogation? They exposed the immorality of the event fearlessly, thus embarrassing oppressors.

2) If you have sour grapes about a job, academic position, or intellectual position, Antifragile might be right for you. Taleb’s litany of Anglican country priests who made impressive scientific discoveries betrays what he sees as the institutional myth. You as a scholar and researcher do not need a big institution to do your work. You can build it on your own. Intellectual entrepreneurship is essentially what Less Wrong and the Rationality community is. Maybe you can’t get into an organization that you want to be part of. There is nothing stopping you from founding your own. Start it as a hobbyist, just as the priests which made so many scientific discoveries did.

3) One thing Antifragile helped me see is the high amount of optionality in my current job, a job which like everyone I sometimes dislike. Nonetheless, I have enough time in my current job not only to engage in private citizen scholarship, but also to try different things out at work. I have some control over my own destiny: agency, or as Kelsey Piper would say, sovereignty.

4) If you thought Chesterton’s Fence was restrictive. Antifragile introduces a whole new level of systemic skepticism. Previously, I would analyze systemic strengths and weaknesses based upon how well the system accomplished explicit goals. This is a reasonable way of looking at such things. But now I look beyond “what gets accomplished well or badly” to “What could destroy the system? What random event would benefit the system? How well can the system adapt to variation?” This might be common sense, but, alas, keeping common sense in the forefront of one’s mind is hard.

One consequence of this change of outlook, is that I am more forgiving of chaos, can see the use of “broken” systems, or things that “don’t quite work” (like speed limits). David Friedman was the first to help me see this with his brilliant book Legal Systems Very Different from Ours. Taleb provides some the tools one might need to think this way.

I especially like his analogy about traffic. 80,000 cars can get from A to B in the same amount of time as 90,000 on a particular road. But suddenly at 100,000, traffic gets heavy. At 110,000 gridlock for hours. That’s some serious nonlinearity.

As Scott Alexander has recently shown, the brain intelligence probably works like this. Cortical neurons are not linearly correlated to intelligence.

5) I appreciate Taleb’s insistence on the value of the ancient classics. Although Taleb makes only a small half-convincing argument that time destroys many books and thoughts, the ones that made it through the sieve of randomness are likely to be valuable and especially insightful for those who look to them for insights.

Taleb follows the classical dictum from Horace that the purpose of literature is to “delight and instruct.” Taleb does something more like “entertain and lambast.” Still, I appreciate his vitriol because he brings with him a legion of enemies to fight, swords to cross, and windmills to tilt at.

One place I think this phenomenon of the value of the ancients manifests itself quite clearly is in the Classical model of historical writing, which is similarly for the purpose of instructing important citizens and patricians. And so each of us, thinkers who can and truly do have an effect on our communities as free and equal citizens, can benefit from this type of history too.

Take, for instance, Livy’s introduction to his history of Rome.

The subjects to which I would ask each of my readers to devote his earnest attention are these - the life and morals of the community; the men and the qualities by which through domestic policy and foreign war dominion was won and extended. Then as the standard of morality gradually lowers, let him follow the decay of the national character, observing how at first it slowly sinks, then slips downward more and more rapidly, and finally begins to plunge into headlong ruin, until he reaches these days, in which we can bear neither our diseases nor their remedies.

There is this exceptionally beneficial and fruitful advantage to be derived from the study of the past, that you see, set in the clear light of historical truth, examples of every possible type. From these you may select for yourself and your country what to imitate, and also what, since it is mischievous in its inception and disastrous in its effects, you are to avoid.

Clearly, Livy believes the enterprise of history is instructional. It does not matter whether his history is up to modern standards of historiography, because in any case he will write and give examples that are for the benefit of leading citizens in a city or country. It's up to you decide whether the lessons he offers are worth taking.

Similarly, Diodorus Siculus, another historian gives these awesome examples of rules and constitutions of different charter cities of the ancient world. In Thurii, for example, they abolished the death penalty for cowardice in battle and replaced it with three days of public shaming, under the theory that moral outrage produces better results for courage in the polity than execution, which is both final and less humane (and he gives this reason of humanity!). Another example of an unexpected law in Thurii: If a legislator wanted to change a law, he had to put his neck in a noose during the voting. If he lost the vote, he would be hanged immediately. I must say, that is putting one’s neck on the line, and is far more impressive than mere “skin in the game.”

These examples are mine, but Taleb has hundreds of his own.

One last example of the power of classics. In the opening scene of the TV show “Servant of the People” which got Zelevskiy elected president of Ukraine a few days ago, Zelevskiy, a history teacher, is lying in bed asleep with a copy of Plutarch’s Parrallel Lives across his face.

The moral force of Zelevskiy’s classically inspired, cuss-word infused speech about the importance of history and the evil of corruption, got both the character and the actor elected to president.

6) Taleb’s skepticism about the limit’s of human knowledge and human capacity resonate with what Paul Christiano, George Dyson, and Nick Bostrom have recently been pointing out. Taleb’s insistence on empiricism over rationalism made what was for me a fairly philosophical point about incomputability, extremely visceral. I am reminded of Nick Bostrom’s point about the Manhattan Project paper in which they investigated whether a Nuclear Reaction would cause a chain reaction, burn up the atmosphere, and destroy the earth. The answer the paper gave: probably not. This should not be reassuring to us.

7) I have always been concerned about skepticism, since I, like most rationalists, want to avoid saying we can’t know anything. I cannot believe in a world which has no structure to it or which cannot be understood. Such a world goes against my direct experience in so many ways. There are patterns and regularity. It was not until Antifragile that I realized skepticism could be thought of as a “pro-living” philosophy. The idea being that daily life has primacy over theorizing about life. Instead of creating theories about life and then trying to falsify them, alla Karl Popper. The process of daily life consists in applying rationality to trial and error so that errors are not too costly, and the trials provide new information.

I am reminded of Eliezer’s insistence in Inadequate Equilibria that we need to be bold in just testing out ideas and intuitions, especially if they are low cost. We don’t need to wait for a study or an expert to give us a theory about why something will or will not work. Sovereignty. Liberty. Exercise it. Apply for that position you want and see if you get it.

8) Antifragile reinvigorated my appreciation for Ludwig Wittgenstein. Read Ray Monk’s Duty of Genius if you want to understand the life and thought of Wittgenstein. He is a fantastic person to get to know. Skepticism and an empirical attitude means that one starts with what works in navigating the territory, before one starts theorizing and creating maps.

Aristotle dissected thousands of animals and discovered that dolphins are not fish. He looked at all these parts and then posited ideas about the roles of different organs. Were his biological theories correct? No. But his method was at least correct. Life first, theory second. Or as Aristotle would have it. Start with the particulars we know and start abstracting from there.

9) Taleb is extremely upfront about the book. He gives the main idea in the introduction and again in the epilogue. If you don’t like literature you can just read the Appendix and get the ideas. He puts his cards on the table. This is the core idea:

Things react differently to randomness and variations in their environment. Some things are fragile, some robust, some antifragile – meaning they get stronger because of randomness. Optionality means that the system or thing is a position to benefit from randomness. Some things get weaker because of intervention in randomness. Taleb uses the medical term iatrogenic. He wants to avoid unnecessary interventions as much as possible since they introduce unknown fragilities. In general we should be trying to live and build systems which are antifragile. Most of the modern world is terribly fragile because Seeing Like a State requires building large systems that can harm, chew up, and destroy individuals and communities in an attempt to survive the vicissitudes of time.

The core math of the book is helpful epistemology and philosophy. “There are bad events which cannot in principle be predicted.” Generally, humans find ways of life, habits, and attitudes that are adaptive before we have an account which explain why the behavior or the belief is adaptive. This raises a strange puzzle… is truth necessarily adaptive?

10) Antifragile is another arrow in the quiver of a category of writing I would call anticanonical for the American Institutional Status Quo. Along with Nick Bostrum, James C. Scott, Alison Wolf, Ariel Rubinstein, recent Daniel Kahneman, Samual Bowles, Herbert Gintis, Alasdair McIntyre, David Friedman and Gerd Gigerenzer there is a noticeable growth of skepticism in mathematical solutions to messy problems in this semi-chaotic system called life.

One conclusion to draw: either we will work much harder to downsize risks inherent in our vast interconnected global system, or we will destroy ourselves.