Though numerous studies indicate that youth and young adults who are involved in one or more social service systems have poor educational and employment outcomes, little is known about the pathways to employment and education in this population. In this qualitative study of educational and employment exploration in vulnerable youth, 11 individuals participated in a series of research meetings over the course of several months as they engaged in a work or school transition. The participants’ progress toward self-defined educational or vocational goals during the study period was characterized as steady progress, planned exploration, accidental exploration, and frustrated aspiration. This article discusses findings for the participants whose experiences fit into each of these groups and presents policy recommendations for supporting vulnerable youth through educational and employment transitions.