Background <p>Medical education is becoming a more structured and recognized field of medicine. Beyond working at an academic medical center or doing occasional didactic or clinical teaching, some physicians dedicate significant time and effort to becoming medical educators. Little is known about the ways in which these physicians enter the field of medical education.</p> Methods <p>This qualitative study utilized purposeful sampling to identify medical educators from different institutions and geographical areas, categorized by gender and career stage. Semi-structured interviews were conducted. Data related specifically to participants’ initial interest in medical education and foundational work in this area were identified and evaluated. Reflexive thematic analysis was used to develop themes across items and participants.</p> Results <p>Twenty-two medical educators (11 male, 11 female) were interviewed. The average age of the participants was 51 (range: 31–72). Time from completion of training averaged 18 years (range: &lt;1–41 years). Their paths to medical education were evaluated as part of a larger study examining the motivations of medical educators. The participants described varied ways of entering the field of medical education: by chance, through the influence and direction of others, or via self-advocacy. </p> Conclusions <p>Physicians become medical educators along different pathways, and their stories reflect varied perspectives and interpretations of career influences. Informal channels provide opportunities for some. However, offering positions to known contacts severely limits the number of potential applicants. This process may hinder efforts to create a diverse workforce in medical education.</p>