Douglass spends seven years living with Master Hugh’s family. During this time, he manages to teach himself to read and write, despite lacking any formal teacher. Mistress Sophia, having been reprimanded by her husband for teaching Douglass how to read, resolves not only to stop teaching Douglass but also to stand in the way of him acquiring knowledge by any means. This, Douglass says, she is able to do readily once she gets a taste of the irresponsible exercise of power.
Douglass goes to great lengths to teach himself how to read because he sees education as a step towards emancipation. Sophia, meanwhile, continues to be corrupted by slave ownership.
Douglass observes that slavery has harmed mistress Sophia Auld as much as it has damaged him. She was initially a kind and charitable woman who went out of her way to help the needy, and who didn’t understand that she was supposed to treat slaves as mere property. Quickly, however, she becomes more and more malicious. After ceasing to teach Douglass, she realizes that slavery and education cannot exist together, and begins to go out of her way to quash any of Douglass’s opportunities to learn. For example, she confiscates any newspaper she sees her slave reading and makes him check in with her regularly to ensure that he isn’t reading when left unsupervised.
Sophia’s evolution from caring mistress to malicious slaveholder illustrates the way that slavery harms both master and slave. In order to preserve her own power, she deprives Douglass of any learning opportunity that she can.
Sophia's efforts to stifle Douglass’s education fall short, because Douglass is determined to educate himself. His most successful ploy is to befriend the white boys in his neighborhood, some of whom were poor and hungry, and bribe them with extra bread from the Auld household in exchange for brief reading lessons. These young boys are sympathetic to Douglass’s enslavement, and Douglass refrains from thanking them by name so as to save them the embarrassment of having aided a slave.
Douglass’s experience being taught by the altruistic white boys shows that a human bond can develop even in slavery’s extremely unjust conditions. Douglass’s ability to bribe the boys with bread also highlights the inequalities present even in white society—Douglass, a slave, is better fed than the poorest whites. And yet, he knows that trying to forge a truly equal relationship—including sharing names—would make any such interaction with those boys impossible.
After Douglass learns to read, he comes across two books that he reads over and over. The first is called The Columbian Orator, and in it a slave addresses his master with a compelling case for emancipation. The slave’s argument proves convincing, and his master elects to free him. In another book, Douglass reads arguments against laws that restricted Catholics’ rights. These two texts convince Douglass that the truth can be powerful enough to overcome slavery, and they give him an opportunity to hone his arguments against the inhumane practice.
While Douglass’s reading brings him an intellectual means of confronting his enslavement, it also forces him to further abhor his enslavers. This painful awareness occasionally makes Douglass see his literacy as a curse rather than a blessing, and wish to be an unthinking beast. Now that Douglass is aware of freedom, he is tormented by his enslavement.
Douglass becomes miserable, and begins to regret his existence and wish himself dead. Meanwhile, he listens intently to any discussion of slavery that he can overhear, and he becomes aware of the concept of abolition. He doesn’t understand precisely what the word means, but the context in which he hears it used clues him in to its great importance. Finally, Douglass gets his hands on a newspaper that describes a petition to abolish slavery, and he understands the word’s significance.
While Douglass languishes in pessimism for a short time, he never gives up hope entirely, and his determination to continue to learn the truth about his situation pays off with his discovery of the abolition movement.
Douglass encounters two Irish dockworkers, who sympathize with his life of enslavement and encourage him to run away to the north. Douglass pretends to be uninterested in what the men tell him, fearful that they might try to betray him and capture him for bounty if he shows enthusiasm for running away. Privately, though, Douglass resolves to run away.
Douglass’s duplicitous behavior in front of the dockworkers shows that he is unable to safely confide in anyone else and reaffirms the tragic slave maxim, “a still tongue makes a wise head.” This is a critical moment for Douglass, as this is the moment he dedicates himself to gaining freedom.
Before he runs away, Douglass’s primary goal is to learn how to write. His initial technique is to watch the carpenters in the shipyards, who label pieces of wood with letters that correspond to their position in the ship. Once he has mastered the four letters the shipyard can teach him, Douglass challenges white children to writing contests. The white children invariably best Douglass, but in so doing, they teach him letters he did not know before. Douglass takes advantage of time he spends around the house unsupervised, and completes the empty pages in spelling books that belong to the Aulds’ son, Thomas. After years of effort, Douglass learns to write in a script that resembles Thomas’s.
Part of the arguments for slavery put forward by slaveholders was that blacks were incapable of freedom or learning. Douglass’s resourcefulness in learning how to write, and his monumental success, would have proven to white readers that blacks are in fact capable of operating at the same intellectual level as whites. Douglass is presenting himself as a truth that white slave owners can't deny—the truth that blacks can learn, and can be just as eloquent as white men. Douglass establishes himself as a living argument against slavery.