Middle-class prosperity is the cornerstone of the American Dream. Americans believe that through hard work and education families can enter the middle class and keep on climbing. However, recent evidence shows that, even with a rebounding U.S. economy, working and middle-class families are struggling more than in decades past, and upward economic mobility may not be continuing, even for those who work hard and play by society’s rules. Moreover, the road to middle-class prosperity is even rockier for minorities. Several time-honored pathways that lead to the middle class are postsecondary education, good jobs, living in viable neighborhoods, personal financial prudence, and entrepreneurship. This paper focuses on all but the last of these pathways of opportunity.