Since Richard is "no longer set apart for being sinful," his family leaves him alone. Chapter 5, pg.123 He is transferred to a new school, and is forced to fight for the respect of the other students there. Although he is enrolled in fifth grade, two years behind his age, he quickly gets promoted to sixth. Feeling like he can do anything in the world, he dreams of being a doctor and decides to get a job. However, Granny will not allow him to work on holy Saturday, and no job will allow him that day off. Bored and frustrated, he wanders around town, giving up his noontime meal to explore even though he is starving. One of his schoolmates alerts him of a job delivering newspapers, which both of them appreciate since the paper carries a pulp story section. He sells the papers for a little while, until a man calls him aside. The man asks Richard if he has read the paper itself, and he answers no. It turns out that the paper is produced by Ku Klux Klan sympathizers. "I said to myself, that boy just doesn't know what he's doing," the man tells him. Chap.5, pg. 132 Richard is shaken and grateful to him, and again realizes the problems that come with trusting white employers.
Richard's struggles with Aunt Addie continue, and he sees that often religion is used to exert power over people: "The naked will of power seemed always to walk in the wake of a hymn." Chapter 5, pg. 136 At the end of the summer he obtains a job selling insurance to poor blacks, and he is shocked at how naive his clients are: they seem to buy insurance from him because they think it will connect them somehow with a smart city boy.
Richard's grandfather had fought in the Civil War, but was denied his pension because of a bureaucratic error that changed his name from Wilson to Vinson. He writes the government endless letters and falls into extreme bitterness. Finally he dies, and Richard does not know how to handle the somber atmosphere of death: when he runs to tell his Uncle Tom the news, he blurts it out bluntly. Tom chastises him, and Richard is baffled at how angry his mistakes seem to make everyone.
Richard decides to defy Granny and get a job. At first, she tells him to leave the house before he damns them all, but finally her "humanity [triumphs] over her fear." Chapter 5, pg. 144 Only his mother is pleased, and kisses him.
