Young adolescents, and the middle level educators who work with them, face many exciting but demanding challenges during this key period of development. According to stage-environment fit theory, the degree to which middle grades students perceive a good fit between their school environment and their needs impacts their academic and life outcomes. The authors endeavored to build on middle level research by studying the extent to which students’ needs are supported by school environment factors and how this “fit” relates to two academic outcome variables: school enjoyment and aspiration. The sample consisted of middle grades students (N = 1,027) between the ages of 10 and 14. Hierarchical logistic regression analyses were conducted. After controlling for age, ethnicity, and gender, four subscales (Social Skills Needs, Mental Health Needs, Academic and Career Needs, and School Support) were entered as potential predictors. Both models were significant and accounted for ~20% of the variance. This study suggests that middle level educators, counselors, and administrators may benefit from considering ways to enhance the match between students’ and the middle grades’ learning environment, especially by considering non-academic factors as a way to provide indirect, but powerful, support for academic and life success.