The Legal Theory Bookworm recommends Bottlenecks: A New Theory of Equal Opportunity by Joseph Fishkin. Here is a description:
Equal opportunity is a powerful idea, and one with extremely broad appeal in contemporary politics, political theory, and law. But what does it mean? On close examination, the most attractive existing conceptions of equal opportunity turn out to be impossible to achieve in practice, or even in theory. As long as families are free to raise their children differently, no two people's opportunities will be equal; nor is it possible to disentangle someone's abilities or talents from her background advantages and disadvantages. Moreover, given different abilities and disabilities, different people need different opportunities, confounding most ways of imagining what counts as "equal."
This book proposes an entirely new way of thinking about the project of equal opportunity. Instead of focusing on the chimera of literal equalization, we ought to work to broaden the range of opportunities open to people at every stage in life. We can achieve this in part by loosening the bottlenecks that constrain access to opportunities-the narrow places through which people must pass in order to pursue many life paths that open out on the other side. A bottleneck might be a test like the SAT, a credential requirement like a college degree, or a skill like speaking English. It might be membership in a favored caste or racial group. Bottlenecks are part of the opportunity structure of every society. But their severity varies. By loosening them, we can build a more open and pluralistic opportunity structure in which people have more of a chance, throughout their lives, to pursue paths they choose for themselves-rather than those dictated by limited opportunities. This book develops this idea and other elements of opportunity pluralism, then applies this approach to several contemporary egalitarian policy problems: class and access to education, workplace flexibility and work/family conflict, and antidiscrimination law.
And from the reviews:
"This breakthrough book rethinks equality from the ground up, turning the spotlight on unexplored bottlenecks in the pursuit of a more just society. A fundamental contribution." --Bruce Ackerman, Sterling Professor of Law and Political Science, Yale University
"Joseph Fishkin develops the 'bottleneck' metaphor into a powerful lens for understanding the structure of opportunity in our society, and thereby recasts the 'equal opportunity' project in a way that is both novel and resonant with deeply rooted intuitions about fairness." --Cynthia Estlund, Catherine A. Rein Professor of Law, New York University School of Law
"Bottlenecks breaks a major step forward in conceptualizing how to promote meaningful opportunities for human flourishing in a world of pluralism as well as inequality. It is a breath of fresh air amidst stale debates over abstract conceptions of equaliy-but more importantly, it charts a path of conceptual and policy development that has enormous promise." --Rogers M. Smith, Christopher H. Browne Distinguished Professor of Political Science, University of Pennsylvania
"Joseph Fishkin offers a new and important framework for defining equal opportunity - one that gets beyond questions of 'merit.' If what looks like 'merit' is more often than not a result of advantages that can be bought, how can opportunities ever be 'equal'? Fishkin provides an original answer, suggesting new ways to open up opportunities by loosening the bottlenecks that are holding people back." --Lani Guinier, Bennett Boskey Professor of Law, Harvard Law School