If you are speaking of Barack Obama's book, you can find various discussion questions from a study group on his campaign website.
One of the overarching questions in the autobiography is: How are our dreams influenced by our upbringing and environment?
You can consider your values, your parents values, your community's values and how those values shaped what you wish for in life-- what you dream.
Obama's example also shows us how our experiences shape the way we dream and for what we dream. When we experience hardship, we generally dream of justice. So another question you could ask is, "How do our life experiences determine our dreams and aspirations?"