This qualitative case study explores the perceptions of schools, schooling, and teaching prior to and after engagement in a dual enrollment program. Data from nine participants revealed insights into the ways pre-college students thought about careers in teaching, how experiences in the dual enrollment program shaped their interest in teaching, and their perceptions of the pathways to and aspirations for teaching. Pre-college students envisioned teaching as a career possibility due to intrinsic factors, such as intellectual interests and racial identity; these factors were reinforced by family and salient schooling experiences. The dual enrollment program confirmed prior interests in teaching through its focus on the education major, mentoring, and the opportunity to take college coursework at the host university.