The imagery of jail
Jail is shown to be a kind of torture to Reed, because Reed wants to be free. He is a hustler in many ways, someone who makes the best of a bad situation, sometimes bending the rules, sometimes breaking them. But in jail, he is trapped. He tries to escape, and sometimes he does, but in other ways, jail symbolizes the way his culture disenfranchises him. He is also trapped by his vices, which jail exacerbates. In jail, he steals and gambles even more than usual, it seems.
New York in the 1850's
The 19th century portrait of life in New York that Reed offers is one that is surreal compared to modern day. He is in a twilight period, a transitional moment in time, because he is still on the tail end of slavery, and although he isn't a slave, he understands what slavery means for him. He encounters unfettered racism, and his community doesn't accept him. In some ways, New York is different, but in many ways it is the same. He has to hustle to survive, and the city brings a lot of vices to his disposal.
The farm, and slavery
When Reed takes a job on a farm, he feels that his life is verging dangerously close to slavery. The only real differences are that his farmer employer is mentoring him as an apprentice, and that he receives some pay. But otherwise, he notices that the only difference between his life and actual slavery is distance. If he should ever find himself in the South, he might not be paid at all, and he might not have his freedom.
Books, literature, and knowledge
Reed is a smart guy. He is literate, and he loves to read, because knowledge is power, in his opinion. His passion for the written word allows him to write this memoir, which literally is written language. He offers thoughts about books he has encountered, and he talks about literacy and the life-long battle he has endured as a semi-educated person. He is thirsty for more knowledge, but his need for money keeps him focused on other things. Reading is shown to be both a survival instinct and also, a luxury.
