This article questions some of the premises undergirding the discourse of self-study, particularly focusing on its treatment of 'self'. We examine the ontology, authority and ethics of self as they emerge from Oren's reading of self-study literature in light of his scholarship of and experience in contemplative education. Having focused on studying and teaching mindfulness in teacher education, Oren had been an insider to 'the study of self' yet an outsider to 'self-study' when he stumbled upon the S-STEP SIG during AERA 2018. His hopes of finally finding a SIG focused on the self were high; however, during the presentations he attended, he became perplexed and disappointed as 'self' emerged as somewhat peripheral to the matter he had assumed to be at stake. Written as an autoethnography, this paper describes his search for the sources of his discontents aided by Jason, a self-study insider who shares some of his ideas. Responding to calls for self-study that advocate educational change in a broad sense, we point to some ontological, epistemological and ethical commitments centering around self that may have been limiting self-study. We suggest that some of them can be rethought and point to ways in which this can lead to new possibilities for self-study and its expanded impact.