The book is a series of interviews with senior executives focused on mistakes in judgment they made during their youth which to this day are embarrassing and which they would not would not want to see their children or grandchildren repeat. During the interviews the executives shared that during their younger years they lied, stole, contributed to suicide, were racist, or less than tolerant of diversity. A number of additional interviews were conducted on the topic of "best advice given" from parents and others. The premise of the book was that embarrassing moments, errors in judgment, provide a platform of opportunities for children and younger adults to learn from others' mistakes and hopefully avoid repeating.