This article examines the extent to which adolescents' expectations about their future in terms of health and education affect their risk-taking behavior. With data from the National Longitudinal Study of Adolescent Healthy we test the theory that a “nothing to lose” attitude about the future predicts greater involvement in risky behaviors involving early sexual intercourse, selling drugs, and weapon use. We examine the effects of both individual- and school-level conditions. Results provide mixed support for our “nothing to lose” hypothesis. We do find noteworthy school-level effects of “school climate,” including aggregate expectations, mental health, and the prevalence of single-mother families, that influence adolescent risk-taking behavior more than school measures of SES.