Nassim Taleb

The three-way structure

Fragile is harmed by volatility and prefers calm; robust is unaffected by it; antifragile gains from it and prefers disorder. Most modern institutions are fragile — stable on the surface, collapsing under an extreme event. A muscle is antifragile: use strengthens it and disuse wastes it.

Ask it of your own career, your organisation and your finances one at a time. Most people find all three sit in the first column.

The barbell

Ninety per cent extremely safe, ten per cent extremely risky, and nothing in the middle. The logic is that the middle is the most fragile place to stand in a Black Swan: it holds neither enough safe assets to absorb the shock nor enough risky ones to profit from it.

A stable main income plus a small, genuinely wild bet beats a portfolio of moderately risky things that all move together.

Skin in the game

Advice from someone who bears no consequence is noise. Bankers gamble with client money and keep the bonus, analysts recommend what they do not own, politicians decide what will not touch them. Every one of those opinions should be discounted before you weigh the content.

Ask instead what would you do, or what would you have done to your own mother — the heuristic Taleb credits to Gerd Gigerenzer.

What a Black Swan actually is

The defining feature is not rarity but being outside your model's range — not that it seldom happens, but that you never conceived of it. A pandemic was a Black Swan to public health systems and not to epidemiologists. The label is relative to whoever is holding the model.

The survivorship trap

We see the survivors and not the dead, so almost every lesson drawn from success is drawn from a sample that excludes failure, and the graveyard is silent. Studying where returning aircraft were hit tells you to armour the places with no holes.

Startup literature studies companies that lived. The dead ones, which may have done exactly the same things, never got written up. Ask first how many of the failures did this too.