The transition, if not transformation, to outcomes-based medical education likely represents a paradigm shift struggling to be realized. Paradigm shifts are messy and difficult but ultimately meaningful if done successfully. This struggle has engen dered tension and disagreements, with many of these disagreements cast as either-or polarities. There is little disagreement, however, that the health care system is not effectively achieving the triple aim for all patients. Much of the tension and polarity revolve around how more effectively to prepare students and residents to work in and help change a complex health care system.Competencies were an initial attempt to facilitate this shift by creating frameworks of essential abilities needed by physicians. However, implementation of competencies has proven to be difficult. Entrustable professional activities (EPAs) in undergraduate and graduate medical education and Milestones in graduate medical education are recent concepts being tried and studied as approaches to guide the shift to outcomes. Their primary purpose is to help facilitate implementation of an outcomes-based approach by creating shared mental models of the competencies, which in turn can help to improve curricula and assessment. Understanding whether and how EPAs and Milestones effectively facilitate the shift to outcomes has been and will continue to be an iterative and ongoing reflective process across the entire medical education community using lessons from implementation and complexity science. In this Invited Commentary, the author reflects on what got the community to this point and some sources of tension involved in the struggle to move to outcomes-based education.