<p>There is a certain kind of work many of us do on ourselves, in which we effortfully change something core about who we are and what we value. Call this work toward improved valuing, ‘aspiration,’ following Agnes Callard. This paper offers an account of aspiration. This account, which I’ll call the Seeking Understanding account, differs from Callard’s own. As such, it avoids a problem I raise for a view like Callard’s: on it, the aspirant is problematically self-focused. Callard is aware of this objection and responds to it, but, I argue, her response is not adequate. To set up the alternative account of aspiration, I develop a distinction increasingly theorized in epistemology: the knowledge/understanding distinction. I offer reasons for thinking of evaluative understanding as requiring not just intellectual but also affective and motivational engagement with its target. According to the Seeking Understanding account, aspiration is seeking this sort of evaluative understanding. After illuminating the contours of the account, I raise a challenge for it in the form of an interesting question that lacks a ready answer. I take initial steps toward an answer, including an important clarification about the Seeking Understanding account of aspiration.</p>