The day-to-day rigors of medical education often preclude learners from gaining a longitudinal perspective on who they are becoming. Furthermore, the current focus on competencies, coupled with concerning rates of trainee burnout and a decline in empathy, have fueled the search for pedagogic tools to foster students’ reflective capacity. In response, many scholars have looked to the tradition of narrative medicine to foster “reflective spaces” wherein holistic professional identity construction can be supported. This article focuses on the rationale, content, and early analysis of the reflective space created by the narrative medicine-centered portfolio at the Columbia University Vagelos College of Physicians and Surgeons. In January 2015, the authors investigated learning outcomes derived from students’ “Signature Reflections,” end-of-semester meta-reflections on their previous portfolio work. The authors analyzed the Signature Reflections of 97 (of 132) first-year medical students using a constant comparative process. This iterative approach allowed researchers to identify themes within students’ writings and interpret the data. The authors identified two overarching interpretive themes—recognition and grappling—and six subthemes. Recognition included comments about self-awareness and empathy. Grappling encompassed the subthemes of internal change, dichotomies, wonder and questioning, and anxiety. Based on the authors’ analyses, the Signature Reflection seems to provide a structured framework that encourages students’ reflective capacity and the construction of holistic professional identity. Other medical educators may adopt meta-reflection, within the reflective space of a writing portfolio, to encourage students’ acquisition of a longitudinal perspective on who they are becoming and how they are constructing their professional identity.