1. The book traces Barack Obama’s roots to places like Kenya, Kansas and Hawaii, illustrating just how unlikely it was that his ancestors would ever cross paths. Discuss this aspect of the book, and talk about the journey your own grandparents and parents had to travel in order for you to exist.
2. How did the book change your understanding of the role that Obama’s African relatives played in his life?
3. As the nation’s first African American president, Obama is also the grandson of a white World War II veteran turned furniture salesman from middle America. How did the story of Obama’s Kansas grandparents change your understanding of the president?
4. Obama had an unusual childhood in that he was raised, at different times, by his mother, by his grandparents, and by his mother and stepfather. How did this shape him?
5. Obama was raised by his white mother and grandparents, lived in the melting pot of Hawaii and in Indonesia, and gradually began to see himself as African-American. Discuss his struggle with self-identify. How can you relate to this experience in your own life?
6. One of the central themes of the book is Obama’s constant desire to avoid becoming trapped – either by geography, expectations, race, family, or conflict. Discuss how this played out in his life, and how it helped make his political life possible.
7. How did Obama’s experience as a community organizer in Chicago prepare him for the political life to come?
8. The book ends with Obama heading off to law school at Harvard. At that point in his life, in what ways is his future political life predictable? At what specific stages in your own life was your future in the balance – did things turn out according to plan?
9. How do you view Obama the president differently now that you’ve read this book and understand more about his upbringing?
10. Given his past interests and experiences, what do you think Obama will do post-presidency? What would you choose to do if you had a chance to start over?