Kerman is the author of the memoir, and she is a dynamic figure throughout the book. After graduating college, instead of seeking a stable career, she finds Nora, a drug dealer who lures her into a life of overseas adventure. During this time, Kerman considers herself a lesbian, attracted to the bohemian counterculture. However, once things between Kerman and Nora go sour, she moves back to San Francisco and attempts to live a more normal life. During this time, she falls in love with Larry, gets a stable job, and moves into a nice apartment.

While her life changes drastically between the Nora and Larry period, prison is what allows Kerman the space to grow beyond who she used to be. While in Danbury, she realizes that she’s not as stoic as she once thought. Before prison, she considered herself a loner who would rather figure things out on her own than seek the help of family or friends. Once in prison, she realizes just how much she needs other people—not only the friendships of the other women in Danbury but also the love of her family and friends on the outside. The biggest change she experiences is her ultimate desire to let people in, rather than pushing them away.