The next morning, the narrator alights in Jacksonville, tired and achy from his train journey. He asks a kind-looking man whom he assumes to be a preacher (he is correct) for lodging recommendations. The preacher tells the narrator where to go and the narrator finds the the accommodations "neat and not uncomfortable". At the breakfast table, he meets his fellow boarders and learns that they are all cigar makers. The landlords are Cuban, and there are several black boarders, but they all speak Spanish, leaving the narrator unable to understand their conversations. Nevertheless, he does enjoy listening to his companions argue animatedly, gesticulating wildly. The landlords inform the narrator that the winter hotels will not open for two months and suggest that he get a job as a "stripper", someone who strips the the leaves of tobacco from their stems in the cigar factory. The narrator is energized by this new prospect because he will be able to overcome his financial troubles and is generally "eager and curious over the new experience". After speaking with his well-educated and intelligent Cuban landlord at the table for some time, he goes to bed excited for his new job.
The narrator quickly becomes the fastest stripper at the factory and takes on a few young African American pupils for music lessons at night. He picks up Spanish and learns that he has a gift for languages as well as music. He is soon is selected to be a "reader" in the cigar factory, which is a coveted and respectable position in factories with Spanish-speaking employees. The reader sits on a stool in the middle of the factory and reads from the Spanish papers, works of literature, etc. Readers are always highly intelligent and are well respected by their co-workers, and the narrator is honored to take on this new role and leave the tedious job of cigar-rolling behind. Soon, the narrator is making enough money that he gives up teaching his sporadic music lessons, but he keeps his rented piano.
The narrator takes this opportunity to ruminate on the race question, as he feels that his new life in Jacksonville has given him his first major initiation into "the freemasonry of the race". He observes that the black man does struggle, though passively, against the race divide in America. He believes that the "Negro question" is ever-present, and finds it puzzling how obsessed white men are with the race question. If "colored" men see the world through the lens of their race, white men seem to do so as well. He feels it a shame that white men, descended from "the great historic Americans from Washington to Lincoln... are now forced to use up [their] energies in a conflict as lamentable as it is violent."
The narrator then divides "colored" people into three categories. The first category is the "desperate class", which includes ex-convicts, drunks, and loafers. They are full of rage and hate white people, who in turn are afraid of them. While small in number, the narrator thinks these "desperates" give the race a bad reputation. The second class is made up of domestic servants, who are generally "simple, kind-hearted, and faithful"; they tend to love and respect their white employers who, in turn, become fond of them. The third class is the most complex, and is made up of well-to-do and educated African-Americans. They are almost solely concerned with the race question. White people are suspicious of them. When "colored" people are ambitious and successful, their white neighbors often think they are putting on airs. While educated "colored" people may feel some kinship with white Americans, they also feel the brunt of prejudice and discrimination, which inspires resentment. However, the narrator makes it a point to note that this class of "colored" people joyfully engages in American social gatherings, like dances and society dinners, even though they are segregated from their lighter-skinned counterparts.
While there are not too many of this third, educated class of "colored" people in Jacksonville, the narrator notes, he finds the few that are there and joins a literary society. His also enjoys spending time with his co-workers and, like them, starts becoming careless with his money - indulging himself in public balls and weekend excursions. He eventually abandons the idea of going back to Atlanta University. At one of the public balls he attends, the narrator encounters the young Pullman porter who brought him down to Jacksonville. Curiously, the porter is wearing a tie very similar to the one that was stolen from the narrator's trunk in the Atlanta boarding house along with all his money. The narrator decides not to vocalize his suspicion.
At another public ball, the narrator observes the "cake-walk" for the first time. Couples dance elegantly in front of judges, who eliminate the teams one by one based on their skill and performance. The last couple standing receives a "highly-decorated cake" as a prize. The narrator is bemused that some "colored" people are ashamed of the cake-walk, because he considers it an important ritual, and a major contribution to American culture. He claims that "some Parisian critics pronounce [the cake-walk] an acme of poetic motion" (63).
Meanwhile, the narrator is happy with his life and is toying with idea of marrying a girl in Jacksonville when he learns that the cigar factory is closing down. He spontaneously decides to move to New York with a few of his ex-colleagues, who think they will able to find more work up north.
Steaming into the New York Harbor, the narrator waxes poetic on the beauty, glamour, and brutality of the "fatally fascinating" city. He falls under its spell almost immediately. When the narrator and his companions arrive, they go to a lodging house on 27th street and 6th Avenue. That evening, they meet some acquaintances who take them to a house which has been converted into a bar. The party is loud and the narrator marvels at how the men call each other "nigger" in a casual way, as a substitute for "fellow".
He observes a poker game and then a boisterous game of craps. He joins the craps table and immediately experiences a hot winning streak, capturing the attention of everyone in the bar. He is energized by the experience, reveling in his fellow players' envy. He is fully seduced by the rush of gambling. While observing the men around him who have not been so lucky, however, the narrator alludes to a future phase of his life in which he becomes an inveterate gambler.
Leaving the party, the narrator is too excited to go to sleep, so he and his friends go to a place called "The Club". It is also a three-story home, this time with a Chop Suey restaurant in the basement. Inside, the narrator describes the clink of glasses and laughter; the place is alive and full of "brilliancy". The group orders drinks and listens to the piano player. The narrator has never heard ragtime music before, as it has just started to become popular in New York. He is transfixed by the pianist's dexterity, and the music inspires a physical response in him. He notes that ragtime music is so influential that white men often copy the improvisations, publish them, and collect small fortunes because of their popularity. The narrator includes an aside on the merits of popular music, which some cultural elites deplore but which he claims has the seeds of greatness and universal appeal.
After the ragtime piano-player finishes his tune, the narrator makes a point to speak to him and is surprised that the man has had no formal training. He wonders if the man would have been a musical genius if he had been trained, but supposes that such an innovator would have difficulty excelling as an "imitator of the great masters" (74). By the time the narrator and his friends stumble home and go to bed, daylight is breaking.
After having survived the loss of his savings and the terrible train journey south, the narrator achieves a great deal of success at the cigar factory and further impresses the reader with his seemingly endless skills, this time at rolling cigars and learning foreign languages. He also makes the fateful decision to travel to the North -New York- and enters yet another new world filled with ragtime music, gambling, and parties. Each of the steps on his journey allows him to explore different aspects of racial identity in America, and through the narrator, the reader becomes tuned into the cultural landscape at the time.
His views on race noticeably evolve. In these chapters, the narrator criticizes white people for being too consumed by the race question and defends African Americans for their major contributions to the American culture, like the cake-walk, a dance with roots in plantation slavery. However, his rumination on the three different types of "colored" people in Jacksonville is matter-of-fact to the point of being reductive. He exhibits the "white gaze" again as he dispassionately excoriates the shiftless "desperate class" (56) and the "simple, kind-hearted, and faithful" domestic class (57); his words mirror the racism, sexism, and classism that racist white Americans expressed at the turn of the century. The narrator clearly categorizes himself in third group that is made up of the wealthy, educated African Americans; a group that W.E.B. Du Bois called "the Talented Tenth". During the Harlem Renaissance, this "third group" set out to be an example for the race and to create a paradigm shift towards the social and political equality of African Americans. However, just as Johnson details in Autobiography, there were certainly tensions between this "third group" and other African Americans.
One crucial aspect of understanding the context of Autobiography is figuring out which of the narrator's observations match the views of James Weldon Johnson himself. Johnson specifically chose to tell his protagonist's story in the structure of an autobiography; it fit into a long tradition of slave narratives, and was also the preferred format amongst African American writers to depict self-fashioning and demystify the "other" for white American readers. Johnson's narrator, however, does not have such a clear agenda, as he often exhibits harsh opinions when describing the American race divide, revealing the complexities of identity formation. The character's eventual decision (in later chapters) to pass as white was potentially dangerous for Johnson when the novel was published, because African American authors were expected to create characters who would present positive portrayals of African Americans and help to facilitate the progress and integration of the race. Johnson deals with this expectation by including several authorial intrusions and expressing a variety of viewpoints outside of the narrator's.
The critic Heather Russell Andrade has noted several instances in Autobiography where Johnson appears to be revealing his own views. The first example is when the narrator finds out that he is biracial and ruminates on the idea that a "colored" man must view the world exclusively through that lens. In the next paragraph, however, a different voice comes forth to champion "the powerful inscrutability of blackness", reflecting Du Bois's theory of double consciousness. The second example is when Johnson expresses his views through the narrator's millionaire patron instead of the narrator himself. The millionaire tells the narrator that race has to be "acted" out and that it is a construct; he also describes the dispossession of African Americans. The millionaire, who says little up until that point, suddenly becomes a spokesman for the race. The third example of Johnson expressing his own views is also through a supporting character – the old Union soldier on the train, who expatiates on the great contributions of other non-white races to the progress of mankind.
Johnson believed that many traditional aspects of African American culture should be regarded as true American art forms, such as the Uncle Remus stories, the cake-walk, and spiritual hymns. The narrator shares these views as well, noting that these creative modes of expression "have originality and artistic conception" and African Americans have "the power of creating that which can influence and appeal universally" (63). An embodiment of this sentiment is the passage where the narrator discovers ragtime. He muses, "one thing cannot be denied; it is music which possesses at least one strong element of greatness: it appeals universally" (73).