Issue: Expectations of reflection run high in medical practice and medical education; it is claimed as a means to many ends. In this article, the authors do not reject the value of reflection for medical education and medical practitioners, but they still ask why reflection can (potentially) yield so many different benefits, and what that implies for the status of reflection in medical education practice. Evidence: Based on a conceptual analysis of debates about reflection in the philosophical tradition, the authors argue that there are two quintessential gaps that play a role in the proliferation of (potential) benefits. First, reflection deals with bridging the gap between theory and practice; second, it deals with bridging the gap between the individual sense and communal sense. These gaps prevent the systematization of reflection, and they are fundamental to human thinking and experience in any situated environment, which led contemporary research on reflection to list a wide variety of benefits. Implications: The authors argue that if reflection resists systematization, it cannot be learned by following rules or protocols, but only practiced. Then, reflection should no longer be taught and researched as an individual skill one learns, nor as a means to some particular, beneficial end. Rather, one should practice reflection, and experience what it means to be part of a community wherein professionals jump the theory-practice gap constantly in a myriad of situations. Based on their analysis, the authors provide three concrete recommendations for reflection in medical education. First, to give precedence to reflective activities that encompass both gaps wherein situated examples can flourish; second, to use reflective guidelines as sources of inspiration; third, to show reserve about assessing reflection.