This chapter explores some of the ways that might represent a credible way to transform suffering (Jonathan Sacks’s term), avoiding the ethical/spiritual poles of cynicism and credulity. An early example is the pathway from tragic vision to tragic enlargement marked out by Greek tragedy. A close look at Freud’s psychoanalytic theory indicates that it does not represent a genuinely tragic view in the traditional sense but a dissonant blend of stark meaninglessness and at best modest instrumental success. Emanuel Levinas’s account of “useless suffering” makes a more plausible case for a kind of tragic enlargement. Suffering interrupts the ordinary pursuits of life in a gratuitous, senseless manner that if honestly faced reveal the deep frailty and precariousness of the human situation. There one encounters a call to compassion, caring, and responsibility that seems, in Levinas’s words “inscribed in the ethical position of the self as self.” Compassion and humility emerge as key components of the good life. Difficulties that have been noted by otherwise sympathetic critics of Levinas’s moral philosophy and some ways it might be amended are discussed. Several other accounts of deepening and transformation that roughly parallel Levinas’s are reviewed, including Luc Ferry’s more secular “transcendental humanism.” A number of suggestions are made concerning how psychology, drawing on Levinas, hermeneutic philosophy, and a greater wisdom of limits might contribute to a richer understanding of suffering and its possible transformation.