In many ways, we are living and working in an unprecedented time in academic medicine. New technologies, scientific discovery, unparalleled availability of medical information and knowledge are currently paired with increasing (albeit slow) gender, cultural, and now generational diversity of the faculty. To prepare the next generation, we must simultaneously be the student and the teacher. As the student, our charge is to understand the current medical and academic environs and recognize the attributes, experiences, and expectations that each generational cohort brings to medicine. As the teacher, we must identify, extract, and communicate the tenets that remain constants for success in academic medicine today and reject those that are no longer relevant. Throughout the years, the basic motivation that drives success has remained constant while the individuals (the players), the environment, and the definition of success in academics have become more varied.