This retrospective study of professionally successful adults who were academic underachievers during adolescence (N = 31) explored the phenomenological experience of underachievement, with particular focus on potentially interactive factors that might be associated with onset. maintenance, and reversal of underachievement. Underinvolved and nonencouraging parents and teachers, negative parental attitudes toward work, family conflict, lack of career direction, and family transitions were found to be associated with underachievement. Both the adolescents and their parents achieved in nonacademic areas. Findings suggest that personality factors, achiever role models outside of the family, developmental task accomnplishmrent, changes in location, and new academic courses may contribute to reversal of underachievement.