The transition to high school is generally considered as a stressful turning point in adolescent development, but some students experience personal growth (i.e., positive developmental changes) through that experience. It is important to examine the mechanism behind such positive changes to understand various developmental patterns of adolescents during the transition. However, the concept of growth in this research area remains unexplored. Some researchers have questioned whether retrospective, self-reported growth reflects actual positive changes in the perception of personal growth. We elaborated on the concept of growth after high school transition by examining whether retrospective appraisal of personal growth after transition to high school is correlated with measured change in growth. Two hundred and sixty-two Japanese adolescents (aged 14–16 years, 50% girls) participated in surveys right before and right after transition. We assessed five domains of growth, including improved relating to others, identification of new possibilities, increased sense of personal strength, spiritual growth, and greater appreciation of life. The results showed that retrospective assessment of growth and measured change during transition were positively associated, provided the adolescents reported the transition as an important turning point in their lives. Adolescents who experienced salient positive changes across the transition were more likely to engage in intrusive and deliberate rumination and social support than adolescents who reported fewer changes. In summary, retrospective growth covaried with measured change only when adolescents perceived the transition as impactful in their lives.