The purpose of this study was to use feminist critical policy analysis to understand the lived experiences of mothering while attending community college and to suggest institutional transformations that might better support mothering students. The findings are based on the re-analysis of interview data from 13 mothering students. We found that the participants understood their life history, especially the sequencing of their choices, to be wrong or hard, and they wanted their children to make different choices. Many of the mothering students viewed living off the system as negative and working as positive, and they judged themselves based on this political dichotomy. We considered ways institutions could be transformed to address these gendered beliefs. College staff might be trained to help mothering students understand the positive outcomes associated with using social programs for living expenses while earning a college degree. Curriculum specifically designed for mothering students might include child-friendly courses where children have areas for play during class time or having class assignments that involve work with their children. (Contains 1 table.)