In this interactive workshop I explore five aspects of the sense and sensibility of philanthropy that can deepen the counsel of advisors and the philanthropy of clients. First, I review the meaning of a moral biography of wealth and indicate how it is best directed by the discovery rather than the imposition of moral purpose. Second, I explain how philanthropy is a social relation of friendship or care, directed toward meeting the true needs of others and oneself at the same time, responding directly to people in need rather than to the medium by which needs are expressed (for example, in commercial relationships), and is to be understood not as the absence of a self but as a quality of an engaged self. Third, I describe the major motivations that incline individuals toward and mobilize their philanthropy. Fourth, I indicate the implications for fundraising, especially, the use of a discernment approach which enables individuals to make decisions about their philanthropy in an atmosphere of liberty and inspiration rather than in an environment of imposed duty. Fifth, I conclude by broadening the picture from the personal to the communal level by outlining the moral citizenship of care that will deepen societal, cultural, and spiritual life in our current age of affluence.