Abstract Purpose Adolescent Medicine (AM) educators in pediatric residency programs are seeking new ways to engage learners in adolescent health. This mixed-methods study presents a novel self-reflection tool and addresses whether self-reflection enhanced residents' perception of the value of an adolescent rotation, in particular, its relevance to their future practice. Methods The self-reflection tool included 17 Likert scale items on residents' comfort with the essential tasks of adolescent care and open-ended questions that promoted self-reflection and goal setting. Semi-structured, postrotation interviews encouraged residents to discuss their experiences. Likert scale data were analyzed using descriptive statistics, and interview notes and written comments on the self-reflection tool were combined for qualitative data analysis. Results Residents' pre–to post–self-evaluations showed statistically significant increases in comfort with most of the adolescent health care tasks. Four major themes emerged from our qualitative analysis: (1) the value of observing skilled attendings as role models; (2) the comfort gained through broad and frequent adolescent care experiences; (3) the career relevance of AM; and (4) the ability to set personally meaningful goals for the rotation. Conclusions Residents used the self-reflection tool to mindfully set goals and found their AM education valuable and relevant to their future careers. Our tool helped make explicit to residents the norms, values, and beliefs of the hidden curriculum applied to the care of adolescents and helped them to improve the self-assessed quality of their rapport and communications with adolescents. We conclude that a structured self-reflection exercise can enhance residents' experiences on an AM rotation.