Learning by working is omnipresent in healthcare education. It enables people to learn how to perform, think, and interact in ways that work for their specific context. In this paper, I review my approach to studying this process. It centers on the question why healthcare professionals do what they do and how their actions and learning are intertwined. The aim of this paper is to illustrate what I have learned from the research I have been involved in, in such a way that it enables other researchers, educators, and clinicians to understand and study practice-based learning in healthcare workplaces. Therefore, I build on a programmatic line of research to present a framework of practice-based learning consisting of three inextricably linked levels of analysis. The first level focuses on how situations lead to personal experiences, the second level looks at strings of experiences that lead to multiple trajectories, and the third level deals with reifications arising from recurrent activities. This framework, and its interrelations and inherent tensions, helps to understand why healthcare workplaces can be both a powerful learning environment and a frustratingly hard place to change.