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Richard Rorty invokes the concept of Romantic imagination as a vehicle for social change. He argues that humans must see themselves as creators of new descriptions of “reality” rather than observers of it. While I am in substantial agreement with Rorty on the importance of imagination, I argue that his vision of imagination is not strong enough. He uses Shelley’s conception, whereas I argue for Coleridge's. In this paper, I examine Rorty’s reasons for invoking Romantic imagination and then make a case for Coleridge’s stronger conception, as it relates to the teaching of philosophy. When carefully employed, Coleridge’s theory affords educators the conceptual foundation to help students navigate the waters of strict positivism, metaphysical dogmatism, egocentric self-assertion, and vapid relativism.