The purpose of this study is to explore mothers’ experience on their involvement in the careers of their adolescent children and develop a substantial theory based on the results. To address the goal, as participants, this author selected 12 mothers and conducted in-depth interviews with them. The major phenomenon of mothers’ experience in career involvement is ‘to come and go between leading and entrusting and seeking a path for their child.’ This author analyzed actions/interactions influenced by above intervening conditions by time, location,’ ‘consideration and trial and error,’ ‘reflection and adjustment,’ and ‘withdrawal and redefinition.’ This study is significant in that it has concretized the practice and characteristics of career involvement focusing on the inner aspects of a ‘mother,’ the factor crucially influencing adolescents’ career development and explored factors related to it. In this way, this author has been able to provide implications for career counseling for adolescents and their parents’ education.