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Sociologists studying work-family relations among mostly white class advantaged mothers find that inflexible workplaces often contribute to their opting out of the labor market upon having children. Extending this research, scholars find black professional mothers hold more “integrative” views of mothering than white professional mothers, due to histories of racial oppression that require navigating work and family simultaneously. Yet direct comparisons between black and white professional women have primarily been overlooked. This article takes up this omission by centering a group of highly education mothers who have often been left out of work-family debates: the growing number of black and white mothers who homeschool their children. Homeschoolers are a particularly salient group since they tend to be highly educated and opt out of paid employment to homeschool. Through interview data with 67 middle-class black and white homeschool and conventional school mothers, I ask how the decision to homeschool relates to women’s work-family pathways and how this compares to their conventionally schooling counterparts. I find that across school type respondents describe three common factors shaping their pathways: inflexible workplaces, school choice discourse of individualized education in insecure times, and notions of good mothering that focus on preparing their children for their racialized futures, leading to what I call mothers’ “racialized insecurity work.” These findings highlight how the often-invisible labor in which mothers engage during these insecure political times is shaped by racial hierarchy location; black mothers seek to ensure their children achieve self-sufficient futures, while white mothers seek to foster their children’s individual interests. These findings elucidate how race and gender shape women’s work-family pathways.