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Wright enters the fifth grade in Jackson. He is soon placed in sixth grade. He delivers newspapers and works briefly with a traveling insurance salesman.

Wright enters the seventh grade. Running errands for whites, Wright manages to earn enough to buy textbooks, food, and clothes. He reads pulp novels, magazines, and anything he can get his hands on. His grandfather dies.

Wright enters the eighth grade at a new school. He must walk several miles to and from school. Eventually, he is able to buy a bicycle. During the winter, he writes his first short story, "The Voodoo of Hell's Half-Acre," which is published in the spring in the Jackson Southern Register. Leon Alan returns from Detroit.

29 May 1925 Wright graduates valedictorian of his ninth grade. He begins high school, but quits after only a few weeks so he can earn money. He leaves Jackson for Memphis, Tennessee.

Works at the Merry Optical Company in addition to being a delivery boy and dishwasher.

Wright's mother and brother join him in Memphis. Wright begins reading Mencken. From Mencken, Wright develops a reading list which includes Theodore Dreiser, Sinclair Lewis, Sherwood Anderson, Frank Harris, and others. Aunt Maggie rejoins them, and in December, Wright and Aunt Maggie move to Chicago, while his mother and brother return to Jackson.

Wright works as a dishwasher and delivery boy until finding temporary employment with the postal service in Chicago. His mother and brother move in with Wright and Aunt Maggie. His years of poor nourishment lead to his failing the medical examination for a permanent position with the postal service, and he must return to dishwashing. Wright, mother, and brother move into another apartment, where Aunt Cleopatra joins them.

Wright eats and eats in order to gain weight so he can pass the postal health exam; when he passes, he works as a substitute clerk and mail sorter. He makes friends, both black and white, in the post office, writes regularly, and attends meetings of black literary groups.

Following the stock market crash, Wright loses his postal job. His mother, aunt, and brother all suffer poor health. Wright begins work on a novel that reflects his experience in the post office.