The purpose of this study was is to investigate the relationship between transformational leadership in families and psychological well-being and career decision-making self-efficacy. The samples were randomly selected from high school students studying liberal arts in Seoul. 400 survey questionnaires were distributed March 11 through 18, 2010. Among them, 386 completed surveys were utilized as the data for the statistic analyses. SPSS were applied. The main results of the study are as follows. First, adolescent children of mothers with leadership have higher psychological well-being than those from families of mothers without leadership. This has been determined as a result of reviewing the psychological well-being of adolescent children according to their mothers' transformational leadership in the family. Second, the adolescent group with mothers who show transformational leadership in managing the home have higher career decision-making self-efficacy than the group without such mothers. This was determined as a result of reviewing adolescent children's career decision-making self-efficacy according to mother's transformational leadership level in the family. Third, career decision-making self-efficacy according to adolescents' psychological well-being show positive relations by group. That is, adolescents living table lives are more positive about their future. Lastly, when comparing the relative contribution of the mother's transformational leadership in the family and psychological well-being on career decision-making self-efficacy, it has gained more credibility as stage ads. Based on the results, when mothers nurture children with a affection-based autonomy, children gain higher psychological well-being, which leads to firm beliefs about constructive futures. Therefore, for successful and systematic career development, CEO mothers' transformational leadership should serve as its foundation.