It is generally well accepted in health professional education that self-assessment is a key step in the continuing professional development cycle. While there has been increasing discussion in the community pertaining to whether or not professionals can indeed self-assess accurately, much of this discussion has been clouded by the fact that the term self-assessment has been used in an unfortunate and confusing variety of ways. In this article we will draw distinctions between self-assessment (an ability), self-directed assessment seeking and reflection (pedagogical strategies), and self-monitoring (immediate contextually relevant responses to environmental stimuli) in an attempt to clarify the rhetoric pertaining to each activity and provide some guidance regarding the implications that can be drawn from making these distinctions. We will further explore a source of persistence in the community's efforts to improve self-assessment despite clear findings from a large body of research that we as humans do not (and, in fact, perhaps cannot) self-assess well by describing what we call a “they not we” phenomenon. Finally, we will use this phenomenon and the distinctions previously described to advocate for a variety of research projects aimed at shedding further light on the complicated relationship between self-assessment and other forms of self-regulating professional development activities.