In the midst of an information age and a global economy, people around the world continue to face significant inequities at school and in the workforce. Career counselling thus finds itself in a paradigm shift that increasingly stresses the influences of culture and sociopolitical context. One area in which the profession can advance a social justice agenda is through the school-to-work movement. In this article, directions for theory, research, and practice with secondary school-aged youth are discussed using a psychology of working perspective. Specifically, the roles of self-determination theory, critical consciousness, and social support are presented as synergistic mechanisms for fostering school engagement and preventing school dropout. To this end, higher education is viewed as a key institutional partner with programmes based inside and outside of the school. (Contains 1 note and 1 figure.)