We sought to establish a framework to track professional identity formation (PIF) in one individual trainee through the use of reflective writing. Using the same six reflective prompts, one undergraduate medical trainee wrote six reflective essays each year of training which were subsequently analyzed by a faculty member and the author looking for specific themes. 22 of a possible 24 pieces were analyzed and the three major themes that emerged across four years were roots, emotions, and self-doubt. Overall, the themes highlighted the critical nature that an individual’s socio-cultural identity plays in medical professional identity formation. This work serves to emphasize that critical reflection is imperative for professional identity formation and argues that PIF is truly a dynamic interplay between a trainee’s personal identity and the medical community’s established dogma.