Clayton M. Christensen begins the Prologue by describing a tradition that he started in the Harvard course he teaches—building and sustaining a successful enterprise. On the last day of class, Christensen leads an informal discussion on the ways that the atmosphere at class reunions has changed since his initial five-year reunion. Gradually, the optimism at these reunions dissipated, and as the years passed, he discovered that many of his classmates—who seemed to have lives of promise and fortune—struggled in their professional and personal lives, which included divorce and legal troubles. He mentions being a classmate of Jeffrey Skilling, whose role in the Enron scandal landed him in prison. Christensen points out that the Skilling he knew in college was not the same person who swindled so many people; however, Skilling’s life took a turn somewhere along the way.

In Christensen’s class, they use theories to try to predict outcomes for businesses and their own lives. This is the blueprint for How Will You Measure Your Life? Christensen also discusses a 2010 graduation ceremony at Harvard in which he was a speaker. He had been undergoing chemotherapy for an aggressive kind of cancer, one similar to that which claimed the life of his father.