For the will desires not to be dark, and this very desire causes the darkness (Jacob Boehme). Moving through the fundamental question of this paradox, this book offers a constellation of theoretical and critical essays that shed light on the darkness of the will: its obscurity to itself. Through in-depth analysis of medieval and modern sources - Augustine, Pseudo-Dionysius, Eriugena, Dante, Meister Eckhart, Chaucer, Nietzsche, Cioran, Meher Baba - this volume interrogates the nature and meaning of the will, along seven modes: spontaneity, potentiality, sorrow, matter, vision, eros, and sacrifice. These multiple lines of inquiry are finally presented to coalesce around one fundamental point of agreement: the will says yes, yet only a will that knows how to say no to itself, entering the silence of its own darkness, will ever be free.