My dissertation draws from in-depth interview data to compare the schooling choices of 95 mothers living in United States. The sample is split between white and black mothers. Within each racial group, one set teaches their children at home and a second set sends them to public schools. School choice, which places the responsibility of selection on individual families, is central to current U.S. education debates. Yet homeschooling, an option that transfers labor from schools to home, is often overlooked in these debates. To date no research has compared homeschoolers to other schooling families in the same region, or examined the impact of the local education context across these two groups. Prior studies, even those interested in inequality, focus on families who send their children to traditional public schools, charter schools, and private schools, while mostly leaving out those families choosing to homeschool. Yet, U.S. survey data show much growth over the past two decades in the number of white and black homeschooling families. Studies with homeschoolers tend to focus exclusively on them, without comparisons to other schoolers in the region. Thus, my study offers a rich comparative analysis for how school choice initiatives are understood by families who are confronted with the same range of choices, yet are enrolling their children in different sorts of schools. This dissertation expands gender, race, family, and education scholarship on two fronts. First, I find that schooling decisions—both homeschool and public school—draw on the intensive work of mothers. Within the family, mothers are disproportionally burdened with this responsibility of choice. Women’s narratives reflect the intensive work they do to navigate schooling options, while the meaning and experience of this work varies by race. Second, I find that decisions around schooling are shaped by resources and racialized experiences of family (i.e. importance of nuclear and extended family) and schools (i.e. bullying and discrimination). When schooling situations arise in which families are unsatisfied, those with more resources often choose to transfer schools or homeschool. This presumably leaves those with fewer resources behind, and appears to maintain, as opposed to reducing, gender, race and class inequalities across families. These findings support policy initiatives that invest in creating equity across schools so that no family is “left behind” in under-resourced schools.