This proposed symposium would present research that extends the above findings to examine ways to support educational and career outcomes for youth in various contexts (e.g., peer, school, and neighborhood). Each paper in this symposium addresses a different period of adolescence and has a different methodological strength. The first paper longitudinally examines norms of peer behaviors as predictors of early adolescent academic adjustment. The second paper uses a multi-level approach to look at school climate as a predictor of high school students’ future aspirations. The final paper presents data from in-depth interviews with urban adolescents transitioning into adulthood. Taking an ecological approach, all three papers will emphasize ways contexts can support adolescents as they plan for their future. The authors will also discuss evidence for the interconnection between adolescent involvement in risk behavior and their actions towards and hopes for the future. A discussant with experience in both understanding contextual predictors of youth success and evaluating efforts to support the positive development of youth will highlight key findings and unique strengths of the three papers. This will facilitate a discussion of the needed future directions in research as well as implications for preventative interventions to support adolescents as they transition into adulthood.