Historians have correctly interpreted the Gilded Age and Progressive Era as periods in which African Americans faced unpreceded violence, a significant decline in franchise, and the loss of many civil rights. These years however, were far more complex when viewed from the vantage point of African American families who attempted to empower themselves through education, securing employment in white-collar occupations, such as teaching, and working to advance themselves through race betterment groups, including womens clubs and civil rights organizations. Yet some middle-class Black families like the Stewarts not only rejected white societys widely held belief of Blacks as racially inferior and incapable of progress. They also embraced migration as a constructive strategy to advance their individual careers and to elevate the race. In an era when the majority of Black workers had minimal literacy and worked unskilled menial jobs, T. McCants Stewart and his children each graduated from college or professional school, worked in white-collar or professional jobs, and paved the way for the next generation. Yet each also understood that migration outside of the Jim Crow South, including to Africa, the U.S. Virgin Islands, and the territory of Hawaii, held the key to their success. Thus, the Stewarts constructed a new vision of freedom and opportunity and believed that even despite the repressive conditions imposed upon Blacks during the Gilded Age and Progressive Era that there was room for growth and an opportunity to advance their careers. Migration, therefore, should be reconsidered as a viable strategy that some Black families adopted to find their place in American society.