Wright arrives in Chicago in 1927. The lack of segregation in public facilities is a shock to him. After years of dealing with racism, he cannot accustom himself to accept the kindliness or even neutral stance of white people he encounters. For example, he lies to the Hoffmans, his Jewish bosses, by claiming that he took off of work without leave because his mother was sick, when it fact he took off time to take the postal service exam. They know he is lying and why he is lying, but Wright cannot accept that life in the South has changed him so much. Wright quits out of shame. He finds work at a café. At the café, his is forced to tell his employer that the white immigrant cook is spitting in the food and is amazed when the owner, a white woman, accepts his word.

Wright finally manages to bring his mother and brother to a bleak apartment in the southside of Chicago. He is hired as a temporary postal clerk, but his ultimate plan is to secure a permanent position as a postal clerk and to learn to write. His plans for work are stymied because he is too physically frail to meet the weight requirements; after passing the exam, he begins eating voraciously to gain weight.