This article explores the relationship between cross-age peer mentoring and positive life outcomes as defined by the Five Cs: competence, character, confidence, connection, and compassion. Qualified high school juniors and seniors were randomly assigned groups of 4-5 freshmen to mentor through the challenges of transitioning to secondary school. Through a qualitative interview process, 12 former mentors discuss the benefits they have experienced in their lives as college students or productive members of the workforce, ranging from 1-4 years removed from the experience. All mentors found some value to the program as outlined by the Five Cs.