Drawing from recent scholarship that examines schooling and the shifting terrain of youth identities, this study examines the identity constructions of Jessica, a Latina high school student. Our portrait of Jessica is part of a larger longitudinal study in which the middle and high school experiences of three Latinas, including Jessica, were examined. For this paper, we used data gathered from Jessica's four years in high school, which included interviews from Jessica and her mother, and field observations from shadowing Jessica's school days during her junior and senior years. Data analysis illustrated two broad themes: Jessica's relationships with her academics and her social life, including the recent positioning of herself as a mother during her pregnancy in her senior year. Findings suggest that Jessica improvised her positions within various realms of school to both resist and reconfigure discourses that shaped her identities as a student and adolescent. This study argues for more research that examines and explores what youth have to say about their school experiences in order to illustrate the complex ways in which adolescents author themselves in school.