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The life of the historical Buddha, and that of his successors in my own Zen tradition, come down to us as part hagiography and part mythology, amalgamated together both to teach particular spiritual lessons and to offer idealized models of the awakened life. Origin stories of this kind offer us a double-edged sword of idealization, one that establishes a goal that is simultaneously attractive and inspiring and at the same time, one so lofty, that by its very nature, may be made to appear unreachable. This paper explores problematic aspects of such stories in Buddhism, what Lauren Berlant has called “cruel optimism,” and describes some of the consequences when modern practitioners measure themselves against a myth.