The key to the antifragile mentality is what Taleb calls ‘optionality’, namely, the use of degrees of freedom as a proxy for knowledge. In other words, if you do not know what will happen, make sure you have every option covered. Taleb, who appears to enjoy a ‘second life’ existence as a gangster, speaks in terms of having ‘skin in the game’. In gambling circles, it is called ‘spread betting’. In any case, it is psychologically much more difficult than it seems because so much of our sense of reality’s stability rests on the future continuing the past being a ‘sure bet’. Why then waste time and money on outliers? But Taleb counsels that it is better to run slightly behind the pack most of the time by devoting a small but significant portion of your resources to outliers, because when one of them hits, the rewards will more than make up for the lower return that you had been receiving to date.

via Book Review: Antifragile: How to Live in a World We Don’t Understand | LSE Review of Books.