Quote 19
The plan which I adopted, and the one by which I was most successful, was that of making friends of all the little white boys whom I met in the street. As many of these as I could, I converted into teachers. With their kindly aid, obtained at different times and in different places, I finally succeeded in learning to read. (7.4)
When Mrs. Auld stops teaching Douglass to read, he has to find other ways to learn his ABCs, and he eventually does it by making friends with street kids. There's a certain irony in this. Mrs. Auld started teaching him to read before her husband "taught" her that the right way to treat slaves was as animals. So it turns out that his best teachers will be not grownups but children: white kids who haven't yet "learned" the lesson that Mrs. Auld has.
Quote 20
In moments of agony, I envied my fellow-slaves for their stupidity. I have often wished myself a beast. I preferred the condition of the meanest reptile to my own. Any thing, no matter what, to get rid of thinking! It was this everlasting thinking of my condition that tormented me. (7.6)
Douglass works hard for his education, but knowledge comes at a cost. While his learning makes him unwilling to be a slave (which ultimately leads him to his freedom), it also makes his life even harder to endure while he still is a slave. Sometimes he envies the slaves who are uneducated enough to be happy with their lot. The fact that Douglass wants to improve himself makes it all the more painful not to be able to do so.
Quote 21
Never having enjoyed, to any considerable extent, her soothing presence, her tender and watchful care, I received the tidings of her death with the much the same emotions I should have probably felt at the death of a stranger. (1.4)
Is there any bond stronger than the one between mother and child? But Douglass barely spends any time with his mother; in fact, he tells us that he never saw her in the daylight. His mother is such a stranger that he doesn't feel any great loss when she dies. Douglass wants us to see that slavery doesn't just take people away from their families; it prevents them from even having families in the first place.