This paper focuses on data from a study of middle- to upper-middle class Scottish S2 ([approximately]seventh grade) students who participated in Inspiring Purpose, a school-based character development program, during the 2016 to 2017 school year. Directed by their teachers, participating youth reflected on values and future aspirations and researched and wrote about an inspiring person. We examine the hypotheses that youth who select a more proximal inspiring figure and/or make a personal connection with that person will demonstrate higher developmental outcomes in the areas of confidence, contribution, self-reflection, goal development, and self-concept. We connected 230 student posters of inspirational figures, 34 youth interviews, and 462 student surveys. Mixed-method analysis revealed students were more likely to describe proximal figures as inspiring and make explicit personal connections over the course of their engagement with the Inspiring Purpose program. Moreover, youth who made personal connections were more likely to score higher on confidence, general self-concept, and contribution. These results suggest that when youth see themselves in inspiring figures and firmly articulate this connection, this can spur beneficial developmental outcomes.