Medical education research has focused heavily on the creation of physician scientists and the process of specialty choice. Interest in teaching by graduating medical students and how this may impact career choice has been little studied. The following dissertation analyzed first an eight-year set of data from the Association of American Medical Colleges’ (AAMC) Graduating Medical Student Questionnaire to investigate career intentions and their relationship with medical school experiences. In order to further that understanding, interviews were conducted with current faculty. Strong relationships were identified between medical school electives and interactions with faculty and administration and the declared intention to teach. The interviews offered more detail about these relationships, stressing the importance of mentorship and opportunities to teach in medical school. They also gave insight into the lack of preparation they felt for faculty positions, the degree to which their decision making was underinformed, and ways in which they felt unsupported within their institutions. Introducing official mentoring programs for medical students and trainees, offering education about potential career paths, demystifying the faculty reappointment and promotion process, and ensuring support for faculty teaching activities are all ways that we can strengthen the faculty pipeline and increase retention of junior faculty.