I like this book, and agree with its main points. You can find those by searching for "Black Swan" on Wikipedia. Having said I like the book, my comments below start with a few complaints.
Complaint 1. I don't really like the analogy of the black swan from which the book takes its title. Taleb's idea is that biologists used to say that swans had to be white, and if it wasn't white, it wasn't a swan. Then a species of black swan was discovered in Australia. He claims this is an example of a new, totally unexpected event. Everyone knew that Australia existed before, so I doubt anyone was very surprised that when they studied a new place they would find a differently-colored bird. If there are swans on Alpha Centauri, I don't think we have strong predictions about what color they should be. The more surprising black swan events are ones where people believed they understood why a situation not only was a certain way but that it had to be that way. I don't think anyone claimed that there was something about whiteness that was essential to the workings of the bird -- everyone knew it was basically an accident or the result of some mundane force of natural selection. I suppose "black swan" is a pleasing image, amenable to succinct explanation, and has a few properties of what he's getting at.
Complaint 2. Taleb comes across as not very nice, and not very mature in the area of human relationships. The book is full of cheap shots and fantasies about doing bad things to the people he doesn't like. He believes experts and economists and so forth dispense worthless advice, and I bet he's pretty much right. It sounds like he has (figuratively) jumped up and down and shouted this at them for some time, and they not only don't switch careers, they become defensive or go on the attack against him. But there's nose-thumbling -- with very little compassion and very little tolerance. It's very hard to give up your career and watch your earnings plummet, and all people will go through great psychological contortions to justify keeping on as they are. The advice all the rest of us give and get is to not childishly belittle our opponents. On the other hand, he has gotten as far in spreading his message as writing a bestseller. Possibly being mean gets attention, and readers might accept his ideas once he has their attention. Ironically, he suggests in a few places that he views religion as a positive thing, but he hardly shows many religious virtues, Christian or other.
Complaint 3. At one point he describes what happens when people are asked to make estimates of some number, and give a range describing their certainty. On average people are far more confident than they should be. Perhaps 50% of the people are wrong about the number being within a range they were 90% confident it would be within. He then addresses the exceptions. Some people, he notes, will give a ridiculously wide range. If asked for a 90% confidence interval of how many lovers Catherine the Great had, they might say between zero and 10,000. He says they are just not playing the game, and they might as well say so. But there is also the possibility that they are attuned to black swans, that they are taking seriously the possibility that there is some important factor they aren't aware of or haven't considered. (Even 10,000 could be a different lover every day for 30 years). It's unfortunate to dismiss people who actually agree with his point. (None of the numbers above are from the book, but they are good enough to make the point.)
Complaint 4. He makes a key distinction in the book between "mediocristan", where things follow predictable distributions and stunning surprises don't occur (height, weight, longevity), and "extremistan", the realm of black swans (individual wealth, book sales, etc.). I think it is a valid and useful distinction. He admits at one point that for him personally, mediocristan is not very interesting, and what he values in life is in the excitement of extremistan. Self-consciously or not, this is reflected in the very terms he chose. I for one prefer to live in the more predictable realm. If I were picking terms to reflect my values I might call it "harmonistan" or "calmistan" instead of "mediocristan", and might call the other place "wackistan" or "chaoticstan" instead of "extremistan".
Observation 1. A substantial part of the evidence in the book is the failings of human reasoning and intuition, most of which I had run across recently in reading an introductory psychology textbook ("Psychology", 2004, David G. Myers). But changing the world often does involve repackaging old ideas in different ways, hoping to find one to get people's attention. The book is something of a bestseller, so it's on the right track of making these truths more widely known.
Approval 1. I did especially like his section on silent evidence, quite in line with thoughts I have had for some time (see my earlier post "When the news is bad for you"). A cute instance is his consideration of the belief among gamblers that people have beginner's luck, something a clear-thinking person would be inclined to attribute to superstition. He observes that people who started out gambling and had bad luck quite probably stopped gambling, and it was initial success that got people hooked so that they are among the peers that a gambler considers. The ones who had bad luck initially are off doing something else.
Approval 2. He denigrates the economic advice of others and repeatedly implies he has a better idea. I think he quite possibly does. His investment philosophy is buried in the book, but when he finally gets to it he easily describes it in very few words. The gist is to place most of your assets in a very safe vehicle such as T-bills. Put the rest in a variety of highly speculative ventures, because while there's only a small chance that any one of them will pay off, the one that does could give a huge benefit. He doesn't like the more conventional strategy of looking for a fairly good rate of return balanced against some risk because our estimates of the risk are way too low. Brief answers are often the best, especially when a primary contention is that other people think they know too much.
Approval 3. He notes that he grew up in Lebanon in what was a peaceful, stable place, until suddenly the entire world he knew fell apart with the civil war of 1975. He implies that some people try to dismiss his work by saying his thinking is the result of his own personal trauma. I am inclined to accept the factual gist of that observation but frame it differently. His early experience has opened him up to see unpleasant truths that most of the rest of us are not primed to see.
Approval 4. I am fully with him in one key respect. A great deal of the time, the right answer to interesting questions is: "I don't know."
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