In this article, I begin by examining critically the Socratic claim that the unexamined life is not worth living. I identify three clusters of problems with this claim. I then consider the consequences of these problems by contemplating a different view of the relation of self-knowledge to the good life. For purposes of illustration, I draw on the film version of the well-known novel Midnight in the Garden of Good and Evil. In particular, I consider the significance and the limits of a central idea in this film—the notion of an overpaint (literally a painting that has been painted over) and the claim that not knowing what is beneath the overpaint can be enjoyable. I develop this idea with reference to the philosophies of William James and Gilles Deleuze and conclude by describing the ways in which this view reorients the practice of philosophy from wisdom (sophia) to practical intelligence (freeness).

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