Focusing on the transition from school to work, the 21st Century Workforce Commission has recommended closer linkages between secondary schools and colleges and between colleges and the workplace as a means of motivating students toward higher personal goals linked to the world of work. In negotiating the increasingly complex demands of college classrooms and the workplace, students and workers can benefit from equipping themselves with a repertoire of strategies, such as mobilizing internal and external resources, self-monitoring, and evaluating information. These are volitional strategies of self-regulation. This chapter explores how preservice teachers prepare for the transition from college classroom to career through assignments and features of the learning environment designed to approximate the demands of work settings and job-related tasks. (Contains 1 table.)