Our too-young and too-new America . . . insists upon seeing the world in terms of good and bad, the holy and the evil, the high and the low, the white and the black. . . . Am I damning my native land? No; for I, too, share these faults of character!

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Richard arrives in Chicago and finds the city startling. The city’s bleak industrial landscape depresses him and fills him with fears for his success. The casual interactions between blacks and whites bewilder him. He gets a room in the building where his aunt Cleo lives. He goes looking for a job the next morning, and finds one as a porter in a delicatessen owned by the Hoffmans, an immigrant Jewish couple. The work is easy, but Richard has a great deal of trouble understanding the Hoffmanses’ thick accents. Richard wrongly assumes that their occasional impatience with him stems from racism.

Richard muses on the dehumanizing social status of black Americans. He notices that the Hoffmans own and operate their store in a whites-only neighborhood. Tortured by the perpetual uncertainty of his fate, Wright discusses his constant fear that he will inadvertently offend the whites who tolerate his presence in the neighborhood. This fear brings Richard closer to sympathizing with other black people who appear to surrender to racism—people like Shorty. Richard does not approve of such surrender, but he now understands why it occurs.

Chicago inspires in Richard new dreams and desires, but he wonders which, if any, can come true. Rather than focusing on “external events” like lynchings, Richard comes to understand that being black in America is a life of constant “psyche pain,” not merely physical pain. He thinks that few blacks can fully comprehend or tell the story of their pain.

Richard takes an examination to be a postal clerk. Out of fear that the Hoffmans will fire him if he dares to look at another job, he simply stays away from work for three days while he rests and takes the examination. When he returns, he explains his absence with the lie that his mother died in Memphis and that he had to go the funeral. The Hoffmans tell him they know he is lying, but they let him stay because they like him. They insist that they are not like Southerners. Richard is ashamed that he has lied out of fear, but he still cannot admit his lie. He quits his job the following Saturday, without telling the Hoffmans anything, because he is too ashamed to work there any longer.

Richard gets a job as a dishwasher in a café. His white female coworkers seem ignorant, careless, and shallow, but pleasant enough. They occasionally brush against him as they maneuver around the restaurant, which stuns him, because a black man touching a white woman, even inadvertently, is a dreadful offense in the South.

Richard’s white female boss is amused when she finds him reading the American Mercury—the magazine H. L. Mencken edits. Richard is horrified to discover that Tillie, the Finnish cook, spits in the food, and he tells a black girl, recently hired as a salad chef, about it. Richard and the girl want to tell the boss, but they wonder if she will believe them in light of the fact that they are black. The girl finally decides to tell the boss, and Richard confirms her testimony. The boss observes Tillie spitting and fires her immediately.