Both neoliberals and liberals call for mitigating inequality of educational opportunity stemming from circumstances beyond an individual's control. In this article, we challenge the wisdom of making equality of opportunity hinge on emphasizing the distinction rather than the relationship between choices and circumstances. We utilize an empirical analysis focusing on the extent to which certain circumstances beyond the control of low-income urban Black adults (e.g. poverty and community instability) limit their eventual chances for maintaining traditional two-parent households, which in turn limits their capacity to make effective choices instrumental in improving the educational prospects of their children. We conclude from this that collectively bearing the burden of attending to differences in the "quality" of circumstances--in which these voluntary choices are made by poor urban Black parents--is something that we owe to each other whether we are neoliberals or liberals if we share a common normative commitment to equality of opportunity.