Labor and race have shared a complex, interconnected history in America. For decades, key aspects of work—from getting a job to workplace norms to advancement and mobility—ignored and failed Black people. While explicit discrimination no longer occurs, and organizations make internal and public pledges to honor and achieve “diversity,” inequities persist through what Adia Harvey Wingfield calls the “gray areas:” the relationships, networks, and cultural dynamics integral to companies that are now more important than ever. Wingfield chronicles real-life experiences and blends them with history and surprising data that starkly show how old models of work are outdated and detrimental. She demonstrates the scope and breadth of gray areas and offers key insights and suggestions for how they can be fixed.