Intuitively, it seems that imagination plays a large role in our decision-making and thus in bringing about personal transformation. We imagine different futures for ourselves, and then we imaginatively explore which of these futures might be best. Recently, however, several philosophers have expressed skepticism about the ability of imagination to be as useful to us in these contexts as we might have thought. In particular, when the futures being imagined are radically different from anything that we have heretofore encountered, the skeptics charge that imagination is unreliable, since what the transformation will really be like is imaginatively out of reach. In this chapter, after an introduction to imagination and the role it plays in decision-making, I explore the case for pessimism. Via an exploration of two different cases for an optimistic approach, I ultimately conclude that we should reject the pessimist’s claim. Imagination indeed serves as a transformative force in our lives.