In this chapter, the authors focus on three particular dispositions to nurture and develop in their students: a tolerance for ambiguity, naivete or openness to experience, and risk-taking. They identify four facets of the creative pedagogy of literature: teaching as disciplined improvisation, centrality of imagination, modeling and developing creative dispositions, and problem solving. These four facets have implications for instruction, curriculum, and feedback/assessment. The literature on creative individuals includes a number of personality dispositions associated with creative thinking or production. Responding to literature nurtures the creative self while analyzing literature appeals to the rational self. Students’ willingness to take risks often varies depending on their confidence in their ability to generate new and interesting ideas. A creative pedagogy of literature is one that asks students to be creators of knowledge as a result of meaningful interactions with literary texts. Disciplined improvisation requires the teacher to be prepared to explore the literature of study but intentionally flexible to various interpretations.