The purpose of this study was to investigate the effects of free-semester system on career maturity after controlling for self-concept, academic motivation, parent-child relation, school adjustment, via an Institute of Education’s Gyeonggi Education Longitudinal study 7 years(first grade of high school students, 2018). The current study used responses from the 4,815 out of 6,813 students who had experience of the free-semester system. Results obtained from the analyses were as follows. First, there were more students who were satisfied with the free-semester system than were neutral or dissatisfied. Second, the study found statistically significant effects of self-concept, academic motivation, parent-child relation, school adjustment, and free-semester system on career maturity. In parallel with these results, students who were satisfied with the free-semester system had higher degrees of career maturity than those who were neutral. However, students who were dissatisfied with the free-semester system had higher degrees of career maturity than those who were satisfied with the free-semester system. The results could help reduce the gap that already exists between students’ attitudes, thoughts, and experience and the ultimate purpose of the free-semester system.