As the SCLC office is stretched, Angelou takes a significant role in promoting the “Cabaret for Freedom” despite her limited practical and technical skills. She feels ambivalent about the extent to which the practical side of the civil rights campaign is in the hands of white activists, feeling they perpetuate racist stereotypes by encouraging to “sing and dance [their] way to freedom” (69).

The review is a huge success and leaves all those involved feeling buoyed up and optimistic. However, as the series of performances draw to a close, Angelou and the rest of the company find themselves faced with the same trials and struggles as before. Angelou is relieved to be offered a two-week contract singing at a new nightclub in Chicago. However, she is anxious about leaving Guy alone. Guy is eager to convince his mother that he is a “man,” capable of looking after himself. Eventually, Angelou arrives at the compromise that she will hire a housekeeper, Mrs. Tolman, who will come in every day to cook for Guy, look after the house, and keep an eye on the situation.

In Chicago, Angelou befriends the Clancy Brothers, an Irish group who are performing in the same venue.