In academic medicine, the commitment to learning, and to learners, is often one that is lifelong. While there is certainly a focus on obtaining baseline competency in knowledge, skill, and practice, the parameters for what defines these concepts constantly shift and advance as the bounds of knowledge are pushed further forward. This occurs within an environment and community that is rife with opportunities to learn, challenge, and expand one’s knowledge. In fact, many would argue that it is rife with requirements to learn. The learner becomes a teacher, and then subsequently the learner again, fulfilling a cycle of education that when engineered properly in vision and in execution, can be self-perpetuating. This chapter will explore teaching in academia in both theory and practice, with a recognition that an exploration of teaching also requires by default a consideration of learning, and how these co-exist and evolve throughout the duration of a career in academia.