In this dissertation, I argue for three related theses: (1) that radical ethical transformation cannot be self-enacted, (2) that Søren Kierkegaard — against popular interpretations — agrees, and (3) that our inability to radically self-transform has implications for the way we relate to our received values. The first part of the dissertation considers the question of "radical transformation" in historically neutral terms. The second part of the dissertation visits questions of interpretation in Kierkegaard. The third part of the dissertation attempts to stake out a positive position by offering a creative reading of Kierkegaard's *Fear and Trembling*.