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A Lesson from a Titan with Taleb on Being a Complete Asshole

Nov 18, 2020 | Personal Development, Short-form

Reading Time: 4 minutes

This article is part of a regular feature on what we can learn from infamous thinkers and achievers. For each one, we dive into a simple observation, action, or policy that you can take, on-the-ground and in real life. As we explore, you’ll discover the reasoning and rewards for your own personal development.

What do a fool, a drunk banker, and an ancient Greek thief all have in common? Sooner or later, they stumble into the bed they’ve made.


This week, we’re scrutinizing a short saying from Nassim Nicholas Taleb. So, you’ll have to forgive the bad attempt at humor above, referencing some of his works. But Taleb invites a certain type of flippancy in his books and online content. Incidentally, it’s half of what makes him so much fun. Sometimes, aside from the witticisms, you may also suspect he’s playing a game of cat and mouse with his intellectual prey.

Indeed, you don’t have to guess: I’m all about that Machiavellian game. But let’s bring on the quote.


Although Taleb focuses his work on the practical and philosophical aspects of probability, few analyze the other part of his routine.  And that’s how he’s an asshole on a very regular basis. Of course, really, it’s not hard to see why they don’t analyze this part.

First of all, his thinking on risk has become a staple as many people have come to recognize our Age of Chaos. In a time of unbridled insanity, you can’t overlook his contributions to managing the unholy mess. And it’s safe to like this part of him now.

Nevertheless, it’s also easy to chalk up Taleb’s bristling personality to simply that… a personality difference. Of course, Taleb also doesn’t hide this fact. And wears it as sort of a badge of honor. You might suspect that it’s all simply part of his brand. And in that regard, it works just fine, even if people don’t think it’s safe to act the same way.

That’s one answer. And as an INTJ myself, I can shrug my shoulders and say “sure.” Over the years, it’s not hard to get a reputation for being a blunt jerk. That’s “just how you are,” so many people say. And few look beyond this facile explanation to the cost-benefit of acting this way.

Although this answer makes sense on the surface, it misses something important about our day and age. And you can’t miss it in American life now. Take for instance anytime someone says, “oh, but he’s a nice guy.” We all know exactly what they mean.

He’s as dumb as a pile of bricks. But that’s okay.

And when they say you’re an asshole, they also mean something too. In large part, it’s not hard to figure out either. And that’s how you aren’t so polite about the bullshit. Or you take a hard stance against things when you should be more flexible.

And that’s not okay. Or so the sentiment goes.

Still, the interesting thing is that Taleb’s quote is in direct odds to so much of the self-help movement. Moreover, it also runs very contrary to the professional world. Why would this be the case? And why do we need phrases to malign standing your ground? Or showing your short tolerance for nonsense?

The questions practically answer themselves here.

In hindsight, over my career in business and civics, I have known an extraordinary amount of people doing… absolutely nothing. Politicians, consultants, community leaders, even CEOs. Many hide out in their offices and their cubicles. Some are stealing money in some way. And for years, they go around in circles with the same meetings but always with a new roster of industry buzzwords and networking connections.

No, Taleb has hit on what Machiavelli wrote about long ago.

As for changing these institutions all at once, when everyone realizes they are no longer good, let me say that this ineffectiveness, though easily recognized, is difficult to correct, because to do so ordinary practices are no longer sufficient, once ordinary methods have become wicked.

This is a lesson I learned young in my career: you can’t simply walk in and change an organization. Or at least, that’s not how it usually goes. Instead, depraved people have already co-opted the conversation. You know what I mean: the niceness, the political correctness, and the agreeableness.

Everyone’s very comfortable. And the conversation is not much more than stage performance. It’s a sort of currency that has become worthless (except to those who have been denied it). So, how would you break through all that monotony?

You bring a flamethrower.

While that offends some people, it’s the only way left to clear the underbrush. And across organizations, a central problem exists where speaking up more directly, to wipe away the old growth, is shamed. And that shame is a powerful tool of coercion for the status quo, to keeping them comfortable. This even as organizations reach a failing point before your very eyes, and everyone watches.

But in a word, you either stay quiet and become complicit in it all. Or you speak out and cut to the bone.

And make no mistake, when all that’s left is the theatre of nicety, any word against will be sharp. So, it doesn’t actually matter how much of an asshole you are. That’s the biggest takeaway today. Besides, unless you’re a fool, a drunk banker, or a thief, who has time for this type of bullshit anyway?


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