Assessing problems in career decision making among adolescents is important for career guidance and research. The present study is the first to investigate among Swiss adolescents the factor structure and convergent validity in relation to personality of the German-language adaptation of the My Vocational Situation Scale. Two preliminary studies (N = 217) suggested that using a 5-point Likert scale response format would increase scale reliability. The confirmatory factor analyses in the main study with two cohorts (n = 341, eighth grade; n = 303, eleventh grade) confirmed that four main factors, which assess problems with identity, decision making, information, and perceived barriers, underlie the data. The barriers factor was differentiated into aspired vocation and personal situation. Construct validity was supported by significant relationships between favorable personality characteristics (emotional stability, extraversion, agreeableness, conscientiousness, generalized self-efficacy, and internal locus of control) and fewer problems. The results suggest that the vocational identity and barriers scales can be fruitfully applied to research on and the practice of career counseling with adolescents.