1. From Sidney's vivid description of growing up on Cat Island, specifically the ways in which he entertained himself—fishing with a piece of thread and straight pin that he had bent into a hook, swimming, climbing trees to eat the fruit—the reader can assume that growing up outside of modern culture had an empowering effect on the author. What are your strongest memories of growing up? How did you entertain yourself as a child? Do you share Poitier's opinion that modern children are negatively affected by the bombardment of television, radio, cell phones, the Internet and video games? If so, what are some ways parents can curb or counter these influences?
2. The first movie Sidney ever saw was a cowboy movie and when he was asked later what he wanted to be, he replied, "A cowboy in Hollywood." Even though he didn't understand that he was saying he wanted to be an actor, it's obvious that his first contact with cinema changed his life. What was the first movie you saw in a theater? What role have movies played in your life? Can you remember one film in particular that had an extraordinary impact on you?
3. According to Sidney, growing up on Cat Island gave him a unique freedom from the racial tensions in other parts of the world. He writes that there were no mirrors in his house or even on the island that he can remember, and that the color of his skin held no more meaning to him than the white sand or the blue sky. What effect do you think this unique childhood had on the development of Sidney's character as an adult? How did your hometown or neighborhood differ from Sidney's? What was the first time you became aware of your race?
4. In chapter 2, Sidney writes about an interaction he has with a white kid named Carl in Nassau. How do you feel about Carl when he is first introduced, of his matter-of-fact assertion of the social status quo based on the color of one's skin? After Carl's family situation is revealed, how does your opinion of him change? What kind of emotions do you think drove Carl to act the way he did?
5. Sidney goes through increasing degrees of culture shock and racism as he moves from Cat Island to Nassau and then to Miami. In chapter 2, he delivers pharmaceuticals to a white woman's home in Miami, and by not knowing the rules of society, he inadvertently puts himself and his brother's family in physical danger. Have you ever been in a situation like this one, where not knowing the rules of a specific society put you in harm's way? Have you ever been discriminated against racially or for any other characteristic that makes you different? Have you (honestly) ever discriminated against someone else—even unconsciously or unintentionally? How did you become aware of your unconscious prejudices? Was it through a friend, co-worker or family member? What can you do to correct that impulse?
6. Sidney refers to his first two years in New York as his "time of ashes," referencing an African tribal ritual where the young boys must cover their faces with ashes before their initiation into manhood. This down-and-out time for Sidney taught him what it's like to be tested and what it's like to scramble for our livelihood and our dreams. What would you consider your personal "time of ashes?" Does any one event or time period in your past stick out as a time of great challenge, learning or change for you? Who were your inspirations during this time? How did it change you?