If the received views on self-transformation in philosophical literature are correct, then either self-transformation (1) is caused by forces beyond oneself and beyond one's control, (2) is not rational to pursue, or (3) does not ever really happen. In this essay, James Gordon highlights the philosophical puzzle known as the "self-transformation puzzle," as raised by Ryan Kemp, who suggests that transformation of the sort educators are interested in cannot be self-caused: it is either something that happens to a person, or something that, if agent guided, is not full-fledged transformation. Next, Gordon turns to an alternative take on the puzzle that tries to recast the conceptual terrain and offer a new way of thinking about self-transformation, namely, the "aspirational" account of self-change offered by Agnes Callard. He argues that Callard's aspirational account of transformation shows that at least one of the premises of Kemp's argument is false. Finally, he suggests several ways that those interested in transformative education might appeal to the concept of aspiration to revise their educational practices.