This article advocates for the collaboration of counseling psychologists with school counselors, other educators, and mental health professionals to enhance the career development of the nation's children and youth. Drawing from the theory of developmental-contextualism, the authors describe how school-to-work programming in schools can be effectively designed to prepare youth to transition from school to work to life. They describe two collaborative school-based programs that build on counseling psychology's commitment to integrative, theory-based interventions and to rigorous evaluation methods. The two programs presented, Achieving Success Identity Pathways (ASIP) and Tools for Tomorrow, were designed to enhance youth's motivation for academic success and vocational development. A number of implications for training and research are described.