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This study investigates whether a positive outlook on the future—an aspect of future orientation—is associated with adolescents' school enrollment and the number of arrests. Using longitudinal data from the Northwestern Juvenile Project (NJP), which followed youth arrested and detained in Chicago between 1995 and 1998, analyses were conducted on 1,143 participants for school enrollment using multivariate logistic regression and on 1,134 participants for arrest counts using negative binomial regression. Findings indicate that adolescents with a more positive view of the future are more likely to stay in school. Additionally, youth with more positive future orientation experience fewer arrests. These results suggest that a positive future outlook may serve as a protective factor for youth involved in the juvenile justice system as they transition into adulthood.