This article reports on a longitudinal study of school-to-work transitions in four professions: education, social work, physiotherapy, and occupational therapy. Each of these professions is characterized by the need for an undergraduate degree for certification; extensive, supervised internships before graduation; and, to a greater or lesser extent, supervision for beginning professionals after graduation. Students in their last years of university, beginning professionals in their first years of practice, and the experienced practitioners who supervise both these groups were interviewed. The article draws on theory and data to help explain why the move from classroom to workplace is often so difficult, and make recommendations to stakeholders in the training and induction of new practitioners in these professions. The recommendations may be extrapolated to other workplaces. (Contains 1 figure.)