I’m currently in the middle of reading Nassim Nicholas Taleb’s latest book, Antifragile. There is quite the history between myself and Taleb — he was probably one of the first nonfiction writers I ever read. This was 10 years ago, when he published what is probably his most famous work, The Black Swan.

Back then I was a freshman in college and I remember being so intrigued by this book that I recommended it to my freshman year econometrics professor. Two years later, I took one of this professor’s advanced econometrics classes and he encouraged us to read The Black Swan. I asked him how he found out about the book and he said a student had recommended it to him. He’d forgotten my name but the book was definitely remembered!

The themes in Taleb’s work

Many of the ideas in Antifragile are ideas that Taleb has been ruminating on for years and ideas that were featured in The Black Swan. He admits as much: these two books and two others are part of Taleb’s Incerto series.

Fragile means handle the package with care. Antifragile means abuse it to make it better!

It’s hard for me to summarize these books succinctly, but I guess The Black Swan emphasized the notion that our statistical models (especially the Gaussian or normal distribution) are wrong. The tails of the distribution are much more dangerous than we expect. We plan for the known, but we’re most impacted by the unknown. He suggests hedging against massive negative outcomes, but without trying to predict what the negative event that triggers losses actually is.

Interestingly, it sounds like Taleb walked the talk: he shorted some of the stock that went under during the 2008 financial crisis. I believe he also profited from the crash through other financial instruments, but am too lazy to look up the details. Suffice it to say, Taleb can probably lay claim over one of the most profitable instances of “I told you so” in history.

In Antifragile, Taleb extols the virtues of antifragility: something that gets better the more it is subjected to volatility and external pressure. He believes that a lot of modern life is fragile and topples easily when faced with a negative event. Taleb contrasts post traumatic stress with post traumatic growth: the former is a symptom of fragility, the latter shows antifragility.

Is it me or is it him?

While I can’t say I’m a Taleb mega-fan (I am reading Antifragile about five years after it was published whereas I read the last Harry Potter installment the day it came out), I still consider him an influential voice into how I think about business.

Why then am I feeling so inadequate when reading Antifragile? It’s hard to put into words (curse my lack of practice with the written word), but Antifragile has me on the fence.

On the one hand, I love some of the ideas it covers, especially the concept of antifragility. On the other hand, I find parts of the book to be borderline unreadable.

The problem is, I really liked Taleb’s writings before. He’s obviously an extremely gifted man, much wiser than myself, with a distinguished career behind him. Is it really that his writing is tough to digest or am I just too dense to comprehend it? The book has at times left me scratching my head and feeling unworthy.

Again, I’m a big fan of the core of his ideas. He and I share a passion for reading: I too read the classics like Dostoyevsky and Zola in high school (although to my shame I have yet to reread them). Taleb dislikes the overly processed and simplified, much like I do (or at least I think I do?). I remember complaining to some of my MBA peers that all our textbooks need to include cartoons or pictures because we Millennials can’t process plain text — we’re just grown children who can’t follow instructions without pretty pictures. I suspect Taleb would agree with me that a lot of the stuff we have going on amounts to infantilization.

Has my brain turned to mush and can it only process cartoons for adults and short sentences? Or is it really that I had more time and bandwidth back in the day and could spend more time digesting ideas? Or is Taleb’s writing in Antifragile just too inaccessible?

I’m now at Chapter 17 and the read has turned into a slog for me. This chapter covering some ancient philosophers has been the toughest so far. I wanted to protest by writing a review of this book much like I did for Atlas Shrugged, but I am too concerned that I am missing the point and would butcher/misunderstand Taleb’s ideas to the point that whatever I write would be laughable. As a side note, I feel like Taleb and Rand would get along swimmingly on certain topics — they both seem to have a disdain for not thinking through the second order consequences of certain policies. On other topics though, Taleb argues for nationalization, which would surely grate the libertarian Rand.

For what it’s worth, I turned to The New York Times review of the book to see where others stand on the quality of the book. It seems they share some of my frustrations. But maybe we’re all just missing his point. He’s the one who’s made a fortune out of this. Maybe both me and the NYT should sit down and shut our traps. Maybe we’re in that mushy, gooey middle whereas Taleb is on the other side, on the solid ground of truth.

How I hate this uncertainty

This is not the first time I’ve felt uncomfortable, unable to decide what’s what. You see, for many things, I am clearly unqualified. For others, I am fairly confident I know what I’m talking about.

It’s the sticky middle that frustrates me, because I’m unsure how to react.

Take a complicated programming question. I may try to learn about it or understand it superficially, but I know very well where I stand. I know that I don’t know. On the flip side, there are some topics where I feel I can put forth a clear opinion: the Australian private equity industry, macarons and some of the insidious impacts of communism in Romania. I know that I know. I probably don’t know everything, but I know enough to confidently express myself.

But with Taleb’s Antifragile, I am uncertain. I might know, but I might also have no idea.

This is such an anxiety-inducing situation for me. It’s also not the first time I’ve felt this way. One other area that comes to mind is my experience interacting with certain high-powered professional men in the US. The numbers seem to suggest there is more sexism in the US than in Europe. After moving to the US, I’ve also found myself in situations where I felt disregarded or cast aside — feelings that I haven’t experienced before. Take this VIP reception where both myself and a male classmate together approached a male senior partner at a law firm. The partner almost entirely ignored my presence, and barely made eye contact with me. My attempts of inserting myself in the conversation were completely unsuccessful.

Did this happen because the partner was sexist? Was he tired and found it easier to just focus on one person? Or was I doing things wrong and crossing some unknown boundary? It isn’t as huge of a culture shock to move from Europe to the US, but there are still subtle behavioral expectations that I understand now, but hadn’t picked up before.

Is it me or is it him?

I really don’t know. I realize conversations about sexism are popular right now, but I just can’t ignore the voice in my head that says I should reflect on the situation and truly understand whether *I* am doing something wrong as opposed to the counterparty doing something wrong. That’s why I’ve stayed away from a lot of these conversations on sexism, both during the MBA and after.

These uncertain situations are upsetting because I don’t know how to react. Should I condemn that partner as sexist or should I alter my behavior? Should I dismiss Taleb’s writing or should I spend more mental energy trying to truly understand him?

I wish I had an answer, but I don’t. I wish I felt confident enough in my experience and knowledge to swing one way or the other. I want to draw conclusions and clear lessons from most interactions, especially if those lessons can help improve me as a person It’s unsatisfying when I feel I can’t. I’ve come up short.

Funnily enough, Taleb would probably chastise me for my need to draw conclusions and put things into neat boxes. In his work he’s argued plenty of times that people tend to fall prey to the narrative fallacy — attempts to analyze events or items and draw a “logical” conclusion.

In the meantime, I’ll finish Antifragile. Even if the experience hasn’t been as delightful (user friendly if you’re into Silicon Valley slang) as reading All The Light We Cannot See, some of the ideas are still worth it.