This chapter considers the use of imagination in transformative decision-making. While there may be some cases where an experience is so qualitatively different from those one has had that it is impossible to imagine what it would be like, in the majority of cases it is possible to adequately grasp the character of unfamiliar experience by means of imaginative scaffolding. There are people who develop extraordinary imaginative abilities, calling into question the reliability of prima facie judgments about what can be done via imagination. This means that there is no in-principle barrier to using imagination to project oneself into a subjectively transformed possible future and making rational choices on that basis.