This grounded theory study employed in-depth interviews with nine student/parent dyads from eastern Canada. Youth with disabilities, aged 16 to 21, contributed narratives describing high school transitions. Shared experience that transcends disability categories produced powerful results. Three categories emerged: (1) transition facilitators; (2) transition constraints; (3) strategies for meaningful transitions. Higher level analysis revealed further relationships: the connection between perceived lack of support and burn out; the importance of self-advocacy; and the sense of "paving rough roads" for the next generation. The core variable, contextual influences, resonates with the five systems presented in the bioecological model of human development. A model demonstrating the interactions among categories, contexts and ecological systems is presented. This framework provides encouragement and cautionary notes for those working toward a meaningful transition and a place to belong for youth with disabilities. (Contains 2 tables and 1 figure.)