Platonic "paideia" is a mainstream concept in traditional philosophy and humanistic circles generally. It is closely connected with social progress brought about by the dynamics of enlightenment and self-fulfillment, symbolized by the allegory of the cave. The main contention of this paper is that the philosophical grammar of this simile is more precarious than is often recognized. Plato's apparently intuitive narrative blends together two features that do not easily mix, namely explicit, categorical dualisms (down/up, darkness/light), and temporal processes of development. The second feature is superimposed upon the first, more elementary, one, suggesting that a philosopher-teacher can be in charge of mankind's ascent towards illustrious goals. This line of thought conceals a basic rhetorical move built into Plato's "paideia," namely its initial focus on enchained humans in need of liberation. It is from this bleak view of ordinary, 'commonsense' life that the narrative's drive is derived. How might a story about the human predicament without "paideia" look? Ludwig Wittgenstein, in some scattered remarks, provides a suggestion.