This qualitative study uses autoethnography to explore my lived experiences as a Black woman, K-12 teacher, and mother of young children provides an important entry point into the entangled questions of school choice, public school curriculum, and educational administration and policy discourse. I use autoethnographic vingettes to examine of how policies around homeschooling and race in education are enacted and experienced in practice. My research adds to extant literature on Black (mothers) homeschooling through providing a simultaneous individual and policy-level analysis of the decision-making process I undergo to potentially homeschool my own children.