Recent literature has described how the capacity for concurrent self-assessment—ongoing moment-to-moment self-monitoring—is an important component of the professional competence of physicians. Self-monitoring refers to the ability to notice our own actions, curiosity to examine the effects of those actions, and willingness to use those observations to improve behavior and thinking in the future. Self-monitoring allows for the early recognition of cognitive biases, technical errors, and emotional reactions and may facilitate self-correction and development of therapeutic relationships. Cognitive neuroscience has begun to explore the brain functions associated with self-monitoring, and the structural and functional changes that occur during mental training to improve attentiveness, curiosity, and presence. This training involves cultivating habits of mind such as experiencing information as novel, thinking of “facts” as conditional, seeing situations from multiple perspectives, suspending categorization and judgment, and engaging in self-questioning. The resulting awareness is referred to as mindfulness and the associated moment-to-moment self-monitoring as mindful practice—in contrast to being on “automatic pilot” or “mindless” in one's behavior. This article is a preliminary exploration into the intersection of educational assessment, cognitive neuroscience, and mindful practice, with the hope of promoting ways of improving clinicians' capacity to self-monitor during clinical practice, and, by extension, improve the quality of care that they deliver.