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Why You Keep Promoting Toxic People
And How to Spot the Rare Leader
Taleb introduced the term “anti-fragile” to the business community.
Anti-fragility is a quality of systems that perform better when there’s chaos. It is the opposite of fragility.
Taleb provides examples such as evolution in ecosystems or how our muscles and bones become stronger in response to stress.
He leaves us thinking “anti-fragility” is a good thing. And in many cases it is!
We can conclude that if we want to be successful in chaotic environments, we should be anti-fragile.
But we should not conclude that intrinsically anti-fragile things are good things.
Bad Anti-Fragility

Anti-fragile people thrive in chaos
Toxicity is anti-fragile.
In fact, toxic anti-fragility is the cause of the “failing up” syndrome we so often see.
Toxicity is many things, but for this post, let’s pull out these two identifying traits:
Toxic people are often ineffective in their roles and produce subpar results.
Toxic people are very good at blaming others.
You can see that when these two things are combined, you get a nasty loop of bad results → blame → promotion, bad results → blame → promotion.
When we look at hermit kingdoms like Gaddafi’s Libya, we think, eventually, the people will have had enough of his shit and rebel, right?
But it’s actually the opposite that’s true!
The worse a dictator runs their little corner of the world, often, the more popular they are! Their ability to blame others and thus be seen as a savior is rate-limited by the amount of suffering!
If they create more suffering, their power becomes almost limitless!
The more Machiavellian among the group of toxic actors may go out of their way to create chaos to blame others. Still, they’ve got firm competition from their stupid compatriots who create chaos whether they want to or not.
What To Do?
Leadership that’s profitable for all stakeholders often exists at the “edge of chaos.” We need to be ordered enough to exploit opportunities, but also lithe enough to see them.
All around this edge, we fall into a chaotic zone, where no one in the organization really knows what’s going on, and that’s where toxicity thrives most.
There are no quick tricks here. But identifying the goal is helpful. We don’t want to lean too much into “order” (or bureaucracy), as, like chemotherapy, that hurts the bad cells and the good.
We need to understand that good leadership is rare and incredibly valuable.
We need to think like detectives when unraveling bad results in a quarterly report, and follow the evidence rather than pointing fingers.
And, if we do spot a pattern of “failing up” after the fact, we probably need to keep our eye on that individual and part ways at the next opportunity.