In the context of widespread media coverage of economic problems, un- and under-employment, and overwhelming student loan debt, youth are making sense of the prospects of getting a job and value of education. Further, they are assessing the implications of the job market in curtailing or enhancing their future success. School-based and familial relationships may support students in making sense of the job market. The current study focuses on how youth view the economy, its association with academic engagement, and how parental and school-based relationships shape views of the job market and their impact on academic engagement. With an ethnically diverse sample of high school students (N = 624; 54% female), perceptions of the job market were tested as mediators and moderators of the relations between school-based relationships and parenting on academic engagement. Using structural equation modeling, job market pessimism mediated the relation between school-based relationships and engagement. School-based relationships and parenting practices moderated the relation between job market pessimism and academic engagement. At high levels of parental and school support, interpreted as increased centrality and salience of academic success, there was a stronger negative association between job market pessimism and academic engagement. This set of findings indicates that high school students are thinking about the job market in ways that impact their engagement in school. These findings extend theories that have focused on the job market and the likelihood of dropping out of school or enrolling in post-secondary education. These findings are significant because just staying in school is not enough to succeed. With increased emphasis on college and career readiness, students are required to be more planful and purposeful during high school in order to succeed in the job market.