Antifragile · Nassim Nicholas Taleb

Optionality examples

Curated by · reviewed 2026-06-01

Keep your options open and favour bets with small, capped downside and large, open-ended upside. You don't need to predict — just stay positioned to win.

What is optionality? Read the full idea →

5 examples of optionality

  1. The cheap experiment

    A small side project costs little if it fails and could change everything if it hits.

  2. Renting before buying

    Staying flexible lets you seize a better opportunity instead of being locked in place.

  3. The startup's many bets

    Venture investing wins not by picking right every time, but by capping losses and letting winners run.

  4. Skills that travel

    Building broadly useful skills keeps more doors open than over-specialising in one fragile niche.

  5. Saying maybe, cheaply

    Holding a position without big commitment lets you act fast when the picture clears.

How to spot it in yourself

You'll forget most of this by next week.

That's just how memory works. Lock optionality in with a 5-minute active-recall session — spaced repetition, no signup.

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