The study in this article investigated how academic preparation, career development skills, parental assistance, and social/environmental barriers predicted inner-city adolescents' psychological preparation to transition into high school. Results showed that academic preparation, parents' instrumental assistance, adolescents' career development skills efficacy, lack of teacher and peer support, and teenage pregnancy were predictive for both boys and girls. Suggestions appropriate to assist inner-city youth in preparing for high school are offered. (Contains 1 table and 1 figure.)