The extent to which I will fail would perhaps cheer him up, atleast that would cure his pessimism.
There is an anecdote that goes somewhat like this: In later years, when Schopenhauer slowly became known, a man came to talk to him about his philosophy. They met at the place in Frankfurt where Schopenhauer used to eat lunch every day. When the waiter came and asked the interviewer what he would like to eat, he, not knowing the place, said: "Well, a priori, I would take this." Upon hearing that, Schopenhauer was positively outraged - because the term 'a priori', one of Kant's great gifts, was never to be used so carelessly and out of proper context. The interviewer lost all respectability.