In this article, the author uses a personal story to challenge the definition of success--introducing Ann, who comes in last in a swimming competition, but wins after all. He has drawn on his years as a swim coach to generate a series of stories exploring the emotional side of learning and the role of compassion in teaching that too often lie buried beneath the need to score points. He believes that when people expand their definition of success beyond medal counts or profit margins--when they expand this definition in their work, their relationships, their families, even in their sporting activities--they permit themselves a taste of enormity.