Obama recounts his life up to his enrollment in Harvard Law School. He was born in Honolulu, Hawaii, to Barack Obama, Sr. of Kenya, and Ann Dunham of Wichita, Kansas, who had met as students at the University of Hawaii. Obama's parents separated in 1963 and divorced in 1964, when he was two. Obama’s father went to Harvard to pursue his Ph.D. in economics. After that, he returned to Kenya to fulfill his promise to his nation. Obama formed an image of his absent father from stories told by his mother and her parents. He saw his father only one more time, in 1971, when Obama Sr. came to Hawaii for a month's visit. The elder Obama died in a car accident in 1982.
After her divorce, Ann Dunham married Lolo Soetoro, a Javanese surveyor from Indonesia who gained financing for graduate work through the East-West Center. The family moved to Jakarta. When Obama was ten, he returned to Hawaii under the care of his grandparents (and later his mother) for the better educational opportunities available there. He was enrolled in the fifth grade at Punahou School, a private college-preparatory school, where he was one of only six black students. Obama attended Punahou School from the 5th grade until his graduation from high school in 1979. Obama writes: "For my grandparents, my admission into Punahou Academy heralded the start of something grand, an elevation in the family status that they took great pains to let everyone know." There he met Ray (Keith Kakugawa), who introduced him to the African-American community.
Upon finishing high school, Obama moved to Los Angeles, where he enrolled at Occidental College, where he describes living a "party" lifestyle of drug and alcohol use. After two years at Occidental, he transferred to Columbia College at Columbia University, in New York City, where he majored in political science. Upon graduation, he worked for a year in business. He moved to Chicago, where he worked for a non-profit doing community organizing in the Altgeld Gardens housing project on the city's South Side. Obama recounts the difficulty of the experience, as his program faced resistance from entrenched community leaders and apathy on the part of the established bureaucracy. During this period, Obama first visited Chicago's Trinity United Church of Christ, which became the center of his spiritual life. Before attending Harvard Law School, Obama decided to visit relatives in Kenya. He recounts part of this experience in the final, emotional third of the book. Obama used his memoir to reflect on his personal experiences with race and race relations in the United States.