With Love and Prayers: A Headmaster Speaks to the Next Generation by F. Washington Jarvis, Peter J. Gomes

A book of deep and practical wisdom, and uncommon common sense, by one of the nation's most eminent educators. F. Washington Jarvis was headmaster of Boston's Roxbury Latin School, the oldest school in continuous operation in North America. This book, winner of the 2001 Christopher Award, collects Jarvis’s addresses, reprinted from his school’s publications.
His approach is anecdotal. “If it is true that a picture is worth a thousand words, it is ten times as true when you are speaking to young teenagers. They are gripped by the story of how real people cope with real situations. They are interested when you share with them the concrete realities of your own life and experience, and they are almost always willing to listen to adults who actually believe in something, who actually stand for something.”
The author never talks down to his audience. He knows that students are asking the deepest questions, questions about whether life has meaning and purpose. He also knows that teenagers often find themselves caught by surprise in situations where they have to make tough decisions. And he believes that they are willing, even eager, to know how others have coped in similar situations.