As a young man, Henderson moved to New York, joining the Great Migration of hundreds of thousands of blacks from the South to Northern and Midwestern industrial cities in the early part of the 20th century.
[2] Henderson also published two novels, Ollie Miss (1935) and Jule (1946), which dealt with pressures on African Americans in the modernizing South.
[2] David Nicholls suggests that these expressed some of the "individualist ethos" of Booker T. Washington, president of the Tuskegee Institute which Henderson had attended.
They also express contrasts, as Ollie Miss is about an African-American woman near Tuskegee who wants a farm where she can raise her child.
Jule, by contrast, deals with a young man who leaves the South to go to the city in the North, similar to Henderson's own journey of advancement, to an urban center that held the promise of autonomy.