Richard now struggles to survive on his own, refusing to follow in the footsteps of others by becoming a slave,subservient or accommodating with Southern attitudes. Rather, he attempts to flee to the North to escape the prejudice of the South so as to discover for himself a new world beyond. His moving to the North, by train, was thus the beginning of a new life for him.
By so doing, Richard fled, along with masses of other blacks the racism, poverty, and lynch laws of the rural South, bound for Chicago, in hope of finding a better life there. His .Aunt Maggie, who had come down for a visit, joined Richard for the journey by train to Chicago, while his mother and brother returned to Jackson.
On first arriving in Chicago, Richard is taken aback by the city-life and its new social codes. On the streetcar, he observes with surprise a white man sitting next to him unbothered about his color.
Richard feels relieved at last from the brutal environment created by the South. For the North seemed like one which represented opportunity and freedom for him. Wright sees interesting juxtapositions between happenings in Chicago with events from his childhood in the South. In Chicago, Richard must learn to adapt to a new environment, where "color hate" is less prominent and racial boundaries do not control him.
Richard soon finds Chicago to be stimulating and less racially oppressive.Richard is finally able to see instances where people are not blinded by race. But he is presented with other problems. Richard must learn that prejudices are easily adopted. He is subject to mistreatment because of his education, his intellect, his socioeconomic background, as well as his political stance.
Richard soon finds a job as a porter in a delicatessen owned by a Jewish couple: Mr. and Mrs. Hoffman. Richard, tuned by the conditions of life in the South, cannot act naturally with the Hoffmans, as he keeps lying to them. He still feels he must abide by Southern social rules that are applied to blacks. He lies to cover up his own insecurity. For he is unable to comprehend any social interaction with whites beyond the brutal and hateful relationships he has witnessed in the South.
After working for a short time there, Richard hears of a job opening for a postal clerk which required him to take an examination on the following Monday. Unsure of how to approach his bosses to ask for a day off, he simply skips a day and lies to them on his return that his mother had died in Memphis.
After a week, Richard obtains a job as a dishwasher in a North Side café that had just opened. There he is often accidentally bumped into by white girls who sometimes even ask him to tie their aprons for them. He thus realizes that they are free from race-consciousness.
Richard is then employed as a postal clerk, and meets an Irish fellow whom he can relate to. He is eventually introduced into a literary circle with connections to the Communist Party. Richard thus joins the John Reed Club - a Communist organization for the arts ¬ in hopes of learning to write and publish.
Even in Chicago, Richard's actions are conditioned by the social lessons he has learned in the South. After reading a magazine American Mercury, the boss lady enters the kitchen and asks him where he found it and if he understood it. Richard lies that he "found" it instead of saying that he purchased it. Thereafter, he keeps his books and magazines wrapped in newspaper so that no one would question him.
One day, when walking by the kitchen stove in the café, Richard notices that Tillie - the Finnish cook spat into a pot of boiling soup. Afraid that the boss will not believe him if he should report her, he instead tells another black girl who works at the café. At first the girl could not believe, but spies on the cook herself to verify the report. Having verified it, both are now afraid that the boss lady will not believe them. Upon being told, at first, the boss tells the girl that she is crazy. But after she spies on Tillie, who proceeds to spit in the food yet again, she fires her.
In June, Richard is called in for temporary duty in the post office as a postal clerk, at that time the only place educated blacks could find work. But securing a permanent appointment requires that he passes a physical examination where the weight requirement is 125 lbs. So Richard strove to increase his weight by all available means. But no matter how much he eats, he is unable to gain weight. Richard is forced to look for another job. Meanwhile, his mother and brother have come to live in Aunt Maggie's apartment. Aunt Maggie constantly criticizes Richard's reading and studying, and after he loses his postal job, she regards him as a failure. So Richard decides to invite his Aunt Cleo to share an apartment with him, his mother, and his brother. At night, he reads books and tries to satisfy his hunger for gaining much insight on his life and the lives around
Richard is finally able to obtain a permanent night job as a postal clerk after forcing himself to eat. The resulting increased pay allowed them to move into a larger apartment and to start buying better food. Having moved into four rooms at Vincennes Avenue he could now read and write regularly in relative comfort. Though he dislikes the bureaucracy of the post office, he becomes friendly with many fellow workers, both black and white, some schoolmates from the South.
During the day, he attends meetings of local black literary groups, experiments with stream-of-consciousness writing and attempts to understand the "many modes of Negro behavior" through his writing. .He also befriends an Irish young man with whom he has a lot in common, both sharing each other's cynicism and beliefs.
Richard also begins to examine several black groups. This includes a black literary group on Chicago's South Side which he finds almost bohemian and too absorbed with sex for his comfort. Richard thus feels distant from its middle class members. Richard also meets a group called the "Garveyites," an organization of black men and women who seek to return to Africa. He observes their passionate "rejection of America," an emotion that he shares. But despite their similar emotional dynamic, Richard pities them for their inability to realize that Africa is really not their home. He views the Garveyites as naïve for not realizing that Africa is under European imperialism, and that they have already merged too much with the West to return to native Africa. So he did not join it.
Meanwhile, Richard begins to hear of the Communist Party's activities, but pays no heed to it as well. When the 1929 stock crash occurs, and volumes of mails drop, his working hours decrease. His pay also decreases with no positions open for a regular clerk. He eventually loses his job at the post office, but is rehired the following summer for temporary work. The Southside sinks into economic depression.
Aunt Cleo suffers from a cardiac condition, his mother becomes ill, and his brother develops stomach ulcers. A distant cousin offers Richard a job selling insurance, which he accepts. During the year, Richard works for burial as well as insurance societies catering toward blacks. His job allows him, for the first time, to explore the lives of black people in Chicago. But Richard seems to be constantly discouraged by the black culture that exists in his environment. He sells insurance policies to poor illiterate black families, men, and women. Like the plantation families of the South the people he encounters in Chicago seem to him as simpletons. Women who are unable to make regular insurance payments could easily negotiate their way out through giving sexual favors. Through that Richard has a long affair with a young woman obsessed with seeing the circus. She is portrayed as childish and almost stupid, for the only relationships she seemed capable of maintaining were sexual and as Richard observes, her intelligence is simple and limited. Not only did the insurance agents view women as property, but they swindled them out of money by switching policy deeds. Wright writes: "I was in and out of many Negro homes each day and I knew that the Negroes were lost, ignorant, sick in mind and body."
Richard now reads books recommended by a friend William Harper (who will later own a bookstore on the South Side). Amongst the numerous writers, Wright is particularly impressed by Dreiser and Joseph Conrad and spurred on to continue to write. Richard Wright's short story "Superstition" is published in April Abbott's Monthly Magazine, a black journal.
After collecting his premiums in the afternoon, Richard visits the Washington Park where many unemployed black people gather to listen to Communist speakers. He is baffled and angered by the black Communist movement, noticing that in appearance, speech, and mannerisms they attempt to copy from white Communists. Richard criticizes the fact that the speakers adopt the styles of black preachers and tend to over-dramatize the militancy of the masses. Wright questions the understanding of the Communists as well as the abilities of black men and women to solve their social problems.
Richard whilst serving as an assistant to a black Republican precinct captain during the mayoral elections on Election Day stands in the polling booth and realizes the corruption of the entire political process. There and then on the face of his ballots, he scribbles: "I Protest This Fraud."
Meanwhile, the depression having grown worse, Richard is forced to move his family into a small dingy rented apartment. There one morning, his mother tells him there is no food for breakfast, and he must go to the Cook County Bureau of Public Welfare to beg for bread.
Richard begins to assess his social isolation.. His isolation follows him into manhood; just as he found no camaraderie among other black children as a boy, Richard is unable to fit in to any black political or social group. Throughout Black Boy, Wright questions whether the black community is educated enough and strong enough to unify themselves and overcome racial barriers and oppression. Here, he conveys a tone of disappointment because he doubts whether the majority of the black community possess enough insight regarding their social situation. To him, the Garveyites are naïve in their wish to return to Africa. To him, the Negro literary groups are passionless and twisted, and even immature. But when Wright writes that he "caught a glimpse of the potential strength of the American Negro," he shows that he has not lost all hope yet.
