In 1981, Lighthouse Youth Services, a private nonprofit agency in Cincinnati, Ohio, began one of the first independent living programs for adolescents in the state. The local county children's services supervisors and Lighthouse administrators had been hearing numerous stories of youth who had left the county's foster and group homes and were discharged from county custody, only to return several months later stating that they were homeless. The youth were reporting that they had learned a lot from various placements, but their families remained dysfunctional and were still unable to provide a stable place for them to live. This article describes the agency's experiences in the past twenty years and discusses the role of housing in the transition process of youth and young adults. It examines elements of a comprehensive transition process and presents case examples that show how Lighthouse developed living arrangement options that provide different levels of supervision, geographical flexibility, and second chances for youth who cannot handle their first chance on their own. Then, it looks at the strategies used for moving from a protection stance to a supportive letting-go process for youth in transition. It also presents an advice that reflects years of experience with supporting youth in transition and is intended as a guide for practice.