Chapter VII elaborates the idea that with education comes enlightenment—specifically, enlightenment about the oppressive and wrong nature of slavery. Douglass’s reading lessons and acts of reading are, therefore, contiguous with his growing understanding of the social injustice of slavery. Douglass gets his first reading lessons from neighborhood boys and also engages in discussions about the institution of slavery with them. These boys not only provide the means of Douglass’s education, but also support his growing political convictions. In this way, Douglass depicts each step in his educational process as a simultaneous step in philosophical and political enlightenment.

Douglass’s encounter with The Columbian Orator represents the main event of Douglass’s educational and philosophical growth. This book features both a Socratic‑style dialogue between an archetypal “master” and “slave” and a speech in favor of Irish Catholic emancipation. Douglass has a sense of the inhumanity of slavery before he reads The Columbian Orator, but the book gives him a clear articulation of the political and philosophical argument against slavery and in favor of human rights. It allows Douglass to formulate his personal thoughts and convictions about slavery. However, the book also causes Douglass to detest his masters. Painfully, he understands the injustice of his position, but has no immediate means of escape. In this regard, Douglass fulfills Hugh Auld’s prediction that educated slaves become unhappy. Douglass’s unhappiness shows that education does not directly bring freedom. His new consciousness of injustice has drawbacks, and intellectual freedom is not the same as physical freedom.

Chapters VII and VIII further develop the Narrative’s motif of the greater freedom of the city compared to the countryside. Chapter VII takes place in Baltimore and features Douglass’s free movements and self-education. Douglass hardly discusses the Aulds or their cruel treatment in Chapter VII. Instead, he focuses on his intellectually fruitful interactions with people around the city, such as neighborhood boys and dock workers. Chapter VIII, however, deals with Douglass’s time in the countryside. First, Douglass discusses his brief trip back to the Eastern Shore around age ten and then his return to Thomas Auld’s plantation three years later. These disparate historical events are out of chronological order with the events of Chapter VII. They are united in one chapter because of their common rural setting. Douglass portrays the oppressive atmosphere of the rural plantation, where slaves are closely watched, harshly punished, and treated as property.

In Chapter VIII, Douglass elaborates on the idea of slave owners treating slaves as property through his depiction of the valuation of Captain Anthony’s slaves. Douglass ironically describes how Captain Anthony’s slaves are lined up alongside the livestock to be valued in the same manner. Douglass’s irony points to the absurdity of treating humans as animals. Douglass further develops this idea by showing how slaves are frequently passed from owner to owner as property. In Chapter VIII alone, Douglass is under the ownership of Captain Anthony, then Lucretia and Thomas Auld, then Hugh Auld, and then Thomas Auld once again. Douglass’s extended description of the Anthony family’s treatment of his grandmother particularly develops this motif of ownership. Though Douglass’s grandmother lovingly tends the Anthony children for her entire life, they do not grant her freedom even in her old age. Because slave owners value slaves only according to the amount labor they can do, Douglass’s grandmother’s new owners abandon the elderly woman.

Several times in his Narrative, Douglass breaks the conventions of his past‑tense autobiography to recreate a scene imaginatively. In his discussion of the treatment of his grandmother, Douglass imagines that she is still alive as he is writing. He creates an image of her stumbling around her small hut, waiting for death. This imagined scene works in the same ways as sentimental fiction. Douglass evokes the conventional scene of the home hearth surrounded by happy children to contrast it with the desolation of his grandmother’s life. Douglass’s grandmother becomes an object of sympathy—a sympathy meant to translate into outrage and political conviction.