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Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Gates faced several challenges over the course of the events described in the memoir, such as the death of his friend Kent Evans and his administrative hearing at Harvard. What emotions did these scenes evoke as you were reading?

2. What were your first experiences with a computer? How have computers changed over your lifetime?

3. Gates grew to love computer engineering because of the challenges it presents. Have you ever been similarly challenged by a work or school project? Did it make the project more or less enjoyable?

4. How would you respond if your child or friend wanted to drop out of college to pursue their dreams? Do you think Gates’s experience is a reliable model for others to follow?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. How does the book reflect social and technological changes in the 1960s and 1970s? How did these changes affect Gates?

2. Throughout the memoir, Gates stresses the importance of freedom in education. How did his educational experience differ from what you might expect today?

Dive into the book’s structure, characters, themes, and symbolism.

1. What is the impact of ending the memoir just after the founding of Microsoft? Why might Gates have chosen to end the memoir there?

2. How did Gates’s character change across the course of the events described in the memoir? What life circumstances explain these changes?

3. How does the tone of the memoir change when Gates describes his experiences at Harvard? What might explain these changes in tone?

4. How does the memoir reflect a belief in the importance of rivalries? What rivalries were most foundational in Gates’s life?