Adolescents who have to make decisions regarding their future career or academic path can be greatly influenced by parental expectations and other individual and contextual factors. The aim of this study is to explore the impact of adolescent–parent career congruence on adolescents’ well-being and future intention to enroll in a university course. The recruitment of participants took place through a combination of convenience sampling and snowball sampling. A sample of 142 high school students who are managing their decisions for the future completed an online questionnaire. Data were analyzed through a path analysis (SEM) with observed variables, and different indices were evaluated to check the model goodness of fit. The data show that congruence with parents’ wishes has a significant effect on academic motivation, work hope and mattering, which in turn have a positive and significant effect on both future intentions to undertake university studies and on the participants’ occupational well-being. In line with past studies, our results demonstrate correlations between adolescent–parent career congruence in career exploration and decision making, pointing out in particular the influence due to complementary congruence with mothers. Furthermore, our study underscores the important role played by both individual and contextual factors in adolescent well-being and intentions for their future. Finally, implications for the practice of vocational guidance practitioners are discussed.