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Paralyzed by Choice examines the importance of considering more than academic performance of schools and schools districts as parents choose where to send their children to school. Using an autoethnographic approach I recount my homing buying and school selection process. Specifically, the paper contrasts two very different types of schools and school districts, paying close attention to the differential outcomes of children from each type of school. Next, I discuss the “forgotten” contextual factors that are important in the educational and developmental process. The paper then moves on to discuss the potentially moderating role that capital (human, social and cultural) plays in differential educational outcomes. This paper details the decision making process of an upwardly mobile Black middle class families to send their son to a low performing higher poverty school. Particularly, I explore the complexity of school choice for an understudied population in the school choice literature. Although education scholars have begun to include middle class parents in the discussion of school choice, minority parents’ narratives are grossly absent. I hope to add to the literature by broadening the discussion of how parents’ diverse backgrounds help them to negotiate the school selection process. The complexity of my varying identities —mother, wife, upwardly mobile, Black, female, academic, education researcher—created complicated our school selection process but intersection of those very same identities also made the choice possible. In this paper I argue that if we as education scholars are to truly understand all aspect of the school selection process we must begin to utilize intersectional theory. Using a intersectional lens will increase our capacity to think more broadly about the experiences parents from diverse backgrounds have as well how and why those experience lead to similar or differing school choice compared to their non-Hispanic white counterparts.