Based on social cognitive career theory, we examined the mediating roles of job search self-efficacy and outcome expectations in the relationship between adolescent–parent career congruence and job search preparatory behaviors and investigated the influence of proactivity as a moderator in these direct and indirect relationships. Participants were 236 Grade 10 and 11 Indonesian students (mean age 16 years, 67% male), who were attending a vocational education school and would not be progressing to post–high school study. After controlling for educational achievement, we found congruence to be associated with self-efficacy (24% of variance explained), outcome expectations (23%), and job search preparatory behaviors (46%). Self-efficacy, but not outcome expectations, was related to more preparatory behaviors, and self-efficacy fully mediated between congruence and preparatory behaviors. Proactivity moderated the direct relationships between congruence and self-efficacy and outcome expectations, but not preparatory behaviors, and did not moderate any of the indirect relationships.