On Friedrich Nietzsche's The Gay Science (1882, with book 5 added 1887).
What is wisdom? Nietzsche gives us an updated take on the Socratic project of challenging your most deeply held beliefs. Challenge not just your belief in God (who's "dead"), but uncover all your habits of thinking in terms of the divine. Realize how little of your life is actually a matter of conscious reflection, and the consequent limits on self-knowledge. The very act of systematization in philosophy overestimates what we can know; instead, we need a "gay" (in the sense of cheerful, carefree, and subversive) science (in the sense of organized knowledge) that chases after fleeting insights and is able to question, i.e. laugh at, the pretensions of its own activity.
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