Because change is ubiquitous in healthcare, clinicians must constantly make adaptations to their practice to provide the highest quality care to patients. In a previous article, Cutrer et al. described a metacognitive approach to learning based on self-regulation, which facilitates the development of the Master Adaptive Learner (MAL). The MAL process helps individuals to cultivate and demonstrate adaptive expertise, allowing them to investigate new concepts (learn) and create new solutions (innovate). An individual's ability to learn in this manner is driven by several internal characteristics and is also impacted by numerous aspects of their context. In this article, the authors examine the important internal and contextual factors that can impede or foster Master Adaptive Learning.