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We frequently encounter the claim that a particular Jewish educational experience will be “transformative” for the participants. The language may be hyperbole. But it may also point to educators’ aspirations to affect not just knowledge and practice but character and identity. In order to understand this phenomenon—not the phenomenon of the use of the language of transformation, per se, but the phenomenon of aspirational Jewish educational programs—this article develops three case studies (Encounter, the Bronfman Fellowship, and the Wexner Heritage Program). What emerges from these cases is a set of models or theories of transformative change: the Maimonides model, learning a habit such that, over time, habit becomes character; the paradise-and-exile model, becoming a seeker after an ideal that one has glimpsed; and the outsider-to-insider model, moving from a sense of fraudulence to a sense of confidence within a particular domain.

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