I have read read Black Swan and I think Taleb's central thesis is there are valid epistimic gaps in every model, and that suggest there is at least one family of hedge strategies where the goal is to think as creatively as possible about what we don't know, but what could be, so as to reframe that lack of knowledge as a plan to go tromping around in a jungle looking for holes. But to do so requires wide-ranging knowledge across many domains, which is hard to develop.