Nassim Taleb and Daniel Kahneman discusses Antifragility at NYPL.mp4

Antifragile systems are those that improve from disorder, I.e a person that makes a mistake and then learns and grows from it. A fragile system is one that breaks from disorder, I.e a glass that experiences an earthquake. You don't need to know the stressor that will destroy the fragile system, just that the system is fragile. Another example in everyday life is the planner vs the adventurer. Yes it is good to plan, but not if there is no optionality, not if some unforeseen event can cause you and the plan to fall apart. You want to be able to grow and improve the experience from the unforeseen.

Human nature prefers many small wins to one big one and one big loss to many small ones. However, opting for this in systems like financial markets can be fatal. It's much better to have very small non-fatal losses and leave an opportunity for the big winner.