It is difficult to grasp your own stupidity: it’s as if our minds inherently believe they have no limits, that anything they can’t understand isn’t worth understanding. You try to get a sense of your own mind, of its capacity, its weakness, but it is elusive. It pretends to be coterminous with reality - where my mind ends, the world ends, there is nothing else. It is extremely tricky to provoke useful friction between the mind and the world, the telltale grinding or stuttering of the mind’s failure; but it is only at this point that you can do any real thinking. To do philosophy you have to repeatedly provoke your own failure, and then contemplate that moment where your mind collapsed; and then you may “fail better” next time. There is nothing wrong with this kind of failure; if a test pilot’s plane explodes or falls into a lethal spin, that itself yields useful data. But it does no good to pretend you are adequate.Elberry likes to talk about past lives. I prefer to think in terms of the past lives I've lived in this life. If your life is completely congruent it may mean you haven't really been living. Some existentialists focus too much on one point, one moment life turns on to shape the rest. But life turns on myriad moments and valuing one too highly comes at the expense of what life offers at each.
feeling stupid - The Lumber Room
From there we just get to "fail better" in different contexts.