The bulk of sociological work examines African American men who are young, unemployed, and poorly educated. In contrast, we offer a nuanced look at Black men living and working in mainstream society—men in the American mainstream although not always identifying as middle class. From 25 in-depth interviews, our data show an apparent contradiction. We find that men account for their success through their individual choices and declared personal motivation to succeed. Yet, throughout their interviews, these men revealed ways they were exposed to critical interactions and opportunities to a larger social network that provided them with tools for mainstream success. In talking about their experiences, these men shared instances in which their racial identity was questioned.