A sensibility is, on a rough first pass, an emotional orientation to the world. It shapes how things appear to us, evaluatively speaking. By transfiguring things’ evaluative appearances, a change in sensibility can profoundly alter one’s overall experience of the world. I argue that some forms of sensibility change entail (1) risking one’s knowledge of what experiences imbued with one’s prior sensibility were like, and (2) surrendering one’s grasp on the intelligibility of one’s prior emotional apprehensions. These costs have consequences (...) for Laurie Paul’s ‘problem of transformative experience.’ Paul has argued that when we are poised to become someone new, our inexperience generates problems for authentic choice about our own futures. By reckoning with the epistemic losses involved in sensibility change, I show that this problem must not be confined to novel transformations. Prior experience does not guarantee the knowledge or understanding necessary for choosing authentically (in Paul’s sense). If the problem Paul highlights is indeed a problem _at all,_ then, it is a still more pervasive and intractable one than it has been taken to be. (shrink)