Douglass lives in Hugh Auld’s household for about seven years. During this time, he is able to learn how to read and write, though Mrs. Auld is hardened and no longer tutors him. Slavery hurts Mrs. Auld as much as it hurts Douglass himself. The mentality of slavery strips her of her inherent piety and sympathy for others, making her hardened and cruel.
However, Douglass has already learned the alphabet and is determined to learn how to read. He gives bread to poor local boys in exchange for reading lessons. Douglass writes that he is now tempted to thank these boys by name, but he knows that they would suffer for it, as teaching blacks still constitutes an offense. Douglass recalls the boys sympathetically agreeing that he no more deserved to be a slave than they did themselves.
At around the age of twelve, Douglass encounters a book called The Columbian Orator, which contains a philosophical dialogue between a master and a slave. In the dialogue, the master lays out the argument for slavery, and the slave refutes each point, eventually convincing the master to release him. The book also contains a reprint of a speech arguing for the emancipation of Irish Catholics and for human rights generally. The book helps Douglass to fully articulate the case against slavery, but it also makes him hate his masters more and more. This dilemma is difficult position for Douglass and often fills him with regret. As Hugh Auld predicted, Douglass’s discontent is painfully acute now that he understands the injustice of his situation but still has no means by which to escape it. Douglass enters a period of nearly suicidal despair.
During this period, Douglass eagerly listens to anyone discussing slavery. He often hears the word “abolitionist.” In a city newspaper account of a Northern abolitionist petition, Douglass finally discovers that the word means “antislavery.”
One day around this time, Douglass kindly helps two Irish sailors at the wharf without being asked. When they realize that Douglass is doomed to be a slave for life, the sailors encourage him to run away to the North. Douglass does not respond to them, for fear they might be trying to trick him. White men are known to encourage slaves to escape and then recapture them for the reward money. But the idea of escape nonetheless sticks in Douglass’s head.
Meanwhile, Douglass sets out to learn how to write. After watching ships’ carpenters write single letters on lumber, Douglass learns to form several letters. He practices his letters on fences, walls, and the ground around the city. He approaches local boys and starts contests over who can write the best. Douglass writes what he can and learns from what the boys write. Soon, he can copy from the dictionary. When the Aulds leave Douglass alone in the house, he writes in Thomas Auld’s old discarded copybooks. In this painstaking manner, Douglass eventually learns to write.