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This paper is based on a study examining the experiences of 25 high school students in Los Angeles County enrolled in a community college program exploring teaching as a career. Through focus groups, student journaling, observations, and document collection, and utilizing the frameworks of radical imagination (Dyke et. al, 2018; hooks, 2014)) and critical pedagogy (Freire, 2000), this qualitative study explores how participating students re-envision schooling systems as spaces of liberation to counteract existing inequities in schools and provide possibilities of hope for teaching and learning. The study’s findings provide several implications for the future of equity-centered teacher preparation, especially with youth, and the potential role of community colleges as diversifying and expanding teacher pipelines.