Situated within scholarly research on tracking, within-school racial segregation, and student career aspirations, this qualitative study examines how three Black students in the mainstream program at a magnet high school in the Southeastern United States discussed their career aspirations. Results indicate that while each participant aspired to attend college, their isolation from the social and cultural capital needed to successfully apply for colleges and their academic status within their school would serve as hindrances in gaining access to institutions that would help them accomplish their career aspirations. The data reveal a need to challenge educational policy such as tracking that has historically targeted and marginalized students of color and continues to provide unnecessary obstacles as they seek to reach their ambitions.