Through Angelou's experiences, readers gain insights into the political and social atmosphere of the 1950s and '60s. As an exceptionally active and talented individual, her first-person narrative offers a wide-ranging perspective on events. Her personal life is explored in great depth, alongside the public life of a very prominent woman.

Although The Heart of a Woman covers the final years of Angelou's theatrical career, her previously established fame allows her to mingle with some of the most notable figures of her time. For instance, the book's first chapter depicts Angelou's introduction to and friendship with the legendary jazz singer Billie Holiday. This introduction, facilitated by her friend Wilkie, provides readers with a snapshot of the extraordinary yet tragically short-lived singer. While the details about Holiday's life and demeanor are intriguing, the scenes with Angelou seem designed to highlight her own character. The contrast between the hardened Holiday and the nurturing Angelou is stark. As Angelou becomes involved in political activism, readers are introduced to other prominent figures of the era, such as Martin Luther King, Jr. and Malcolm X. Angelou offers a glimpse into not only their historical significance but also their personal identities.

Angelou's son, Guy, is as central to her story as she is. Raised by Angelou, Guy matures in this part of her autobiography. Even while advocating for political causes, Angelou cannot ignore her strong commitment to her maternal responsibilities. She frequently expresses guilt about relocating her son from city to city and school to school in pursuit of better opportunities. Her roles as an entertainer and political organizer often keep her away from home, leaving Guy to fend for himself. Angelou grapples with a challenge faced by many modern black women: "The black mother perceives destruction at every door, ruination at each window, and even she herself is not beyond her own suspicion. She questions whether she loves her children enough—or, more terribly, does she love them too much?" Throughout the book, Guy is a source of ongoing concern and anxiety for Angelou.

A significant portion of her anxiety stems from Guy's absence of a father figure. Angelou consistently evaluates her romantic relationships based on their potential impact on Guy. This concern highlights the challenges faced by single mothers and their sons. She wonders how young men can learn the values and behaviors of responsible manhood without fathers to guide them.

Eventually, Angelou finds a father figure for Guy, but he turns out to be far from a model of responsible manhood. Vus, an African revolutionary with whom Angelou has an informal marriage, is well-educated, articulate, and kind. He brings a wealth of experience into Angelou's life and offers Guy a glimpse into the splendor of his ancestral heritage. However, Angelou soon becomes aware of Vus' financial extravagance and his womanizing behavior. On the surface, Vus appears to be a good father, but beneath his refined exterior lies a machismo that repulses her. Through this, Angelou highlights the challenge of finding truly positive role models. She criticizes many American men she meets for their lack of interest and respect for women. In comparison, Vus, the African representative, fares no better. While Angelou clearly values her cultural heritage, she does not hesitate to expose its darker, paternalistic aspects.