We often take for granted thinking and communication as inherent skills without questioning their accuracy or potential for improvement. In medicine, these skills are required at a significantly more advanced level. To date, the philosophy of medicine has primarily focussed on overarching medical topics, overlooking the role of metacognition—thinking about thinking—in clinical practice. This chapter explores key concepts from interdisciplinary research on metacognitive thinking, drawing from developmental psychology, neurocognition, education and philosophy of mind, to define metacognition within the clinical setting: the implicit and explicit cognitive processes that involve self-monitoring, self-evaluation, self-regulation and self-control of one’s cognition with effect on the clinical decision-making process, patient’s outcomes and physician’s mental well-being. The chapter ends by building a case for metacognitive awareness as an indispensable skill to develop or enhance in clinical practice.