Michelle started keeping a personal journal, in which she would write her feelings occasionally. Her relationship with Barack had progressed to the point where they lived together. The author states that Barack’s intellect and ambition made her question whether she was living her true purpose (Obama 102). Michelle candidly states, "I hated being a lawyer" (Obama 102). The feeling of dissatisfaction in her job, Barack's intellect and ambition, as well as her desire to change the world, made the author completely unsatisfied with her life. While still working at Sidley & Austin, Michelle started looking for new job, unrelated to law.

Michelle and Barack had been in a relationship for a year and a half and started contemplating the idea of marriage. However, Michelle asserts that while she viewed marriage as a “Full-on merger,” Barack viewed marriage as short-lived. Both Michelle and Barack had experienced marriage differently, and thus held varying views.

At the same time, her father’s health was deteriorating. Although Michelle's father often assured the family that he was fine, it was evident to Michelle, her mother and Craig that her father’s health was gradually declining as a result of multiple sclerosis (Obama 105-107). The chapter ends with Michelle visiting her father at the hospital, the two of them looking at each other silently but feeling like they had said everything to each other. It was clear to Michelle that the time had come for her father to say good-bye (Obama 109).