50 pages 1 hour read

Failing Forward: Turning Mistakes Into Stepping Stones for Success

Nonfiction | Book | Adult | Published in 2000

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Discussion Questions

General Impressions

Gather initial thoughts and broad opinions about the book.


1. How does Maxwell’s approach to failure differ from the conventional self-help philosophy of “positive thinking” or “visualization for success,” such as Dr. David Schwartz’s The Magic of Thinking Big? Do you find his emphasis on embracing failure more or less compelling than other motivational frameworks?


2. Maxwell frequently uses historical and celebrity examples to illustrate his points. Which examples resonated most strongly with you, and why?


3. The book was published in 2000. Does Maxwell’s message feel dated or timeless?

Personal Reflection and Connection

Encourage readers to reflect on how the book relates to their own life or work and how its lessons could help them.


1. Maxwell argues that traditional education poorly prepares people for handling real-world failure. Reflecting on your own educational and professional background, where do you feel most unprepared for setbacks, and how has this affected your willingness to take risks?


2. The author emphasizes separating identity from performance—viewing oneself as someone who failed at a task rather than as “a failure.” In what areas of your life do you struggle most with this distinction, and what triggers make you more likely to personalize setbacks?

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