“Do we care to match the reality of America to its ideals? If so, do we really believe that our notions of self-government and individual freedom, equality of opportunity and equality before the law, apply to everybody? Or are we instead committed, in practice if not in statute, to reserving those things for a privileged few?” 

Obama devoted his political career to reshaping the country to adhere more closely to its founding ideals. This quote challenges readers to work to create a more perfect union. It also echoes the title of the memoir, which gestures to the promise of democracy, liberty, and equality made by the founding fathers.

“I experienced failure and learned to buck up so I could rally those who’d put their trust in me. I suffered rejections and insults often enough to stop fearing them. In other words, I grew up—and got my sense of humor back.” 

This passage emphasizes the resilience Obama developed after graduating from Columbia University and taking a job as a community organizer in Chicago. The work entailed asking strangers for help on various projects, such as after-school programs and asbestos removal. Obama genuinely cared for the community he was helping, which kept him motivated even in the face of rejection. Obama drew on this tenacity throughout his political career, working to solve problems even in the face of major obstacles.

“I’d never once heard her dwell on the disappointments. Instead she seemed to find small pleasures everywhere. Until this.” 

This quote is about Obama’s mother, who maintained a positive attitude even through life’s challenges. Dunham remained joyful despite being twice divorced, raising two children on her own, and suffering financial hardships. Her demeaner changed after she was diagnosed with uterine cancer, a disease that left her so weak her saliva glands shut down. Dunham had a profound impact on Obama, even during her illness. Toward the end of her life, she encouraged Obama to pursue a seat in the Illinois State Senate, but only if he had Michelle’s support.