This qualitative case study explores how former Supplemental Instruction (SI) leaders experienced perspective transformation as a result of serving in a peer leadership role at a 4-year, private university through a blended theoretical framework based on the principles set forth by Mezirow and Nohl. Through their participation in interviews and graphic elicitations, former SI leaders offered valuable insights concerning the transformative nature of student leadership and its impact on the emerging sense of self in social and learning contexts. This study also assists in filling the void in research on how undergraduate students benefit by serving in a leadership role within a peer-facilitated academic assistance program in higher education.