This study aims at analyzing the relationship between individual characteristics and satisfaction with high school, university and career. For this purpose, Structural Equation Modeling analysis was conducted on 484 individuals who are currently working after graduation from university with data provided by Korean Education & Employment Panel(KEEP) of Korea Research Institute for Vocational Education & Training(KRIVET). As a result of the analysis, it turned out that there is a causal relationship between individual characteristics and satisfaction with high school, satisfaction with university and satisfaction with career. Among individual characteristics, health has effect on satisfaction with high school, self-conception has effect on satisfaction with university and satisfaction with career, and happiness has significant effect on satisfaction with high school and university and satisfaction with career. Satisfaction with high school has effect on satisfaction with university but does not have significant any effect on satisfaction with career, and satisfaction with university has significant effect on satisfaction with career. Therefore, it becomes apparent that variables which have effect on satisfaction with career are such individual characteristics as variables self-image, happiness and satisfaction with university. This implies that in the continuing course of life from home through school to career, satisfaction with present life has relationship with satisfaction with future life, and especially, to enhance the satisfaction with career, educational service and experience in university are important in addition to employment conditions of a work.