This volume explores and expands a Wittgensteinian account of philosophy as an ongoing transformative practice. It investigates the simultaneously aesthetic and ethical dimension of philosophical exercises, so as to uncover their transformative potential for and within ordinary practice, conceived of as a weave of inherited embodied habits. For this purpose, the volume focuses on three intertwined aspects. First, it analyzes the aesthetic form of Wittgenstein's writings. In particular, it considers the use of pictures, dialogues, comparisons, and instructions as exercises to be enacted by readers, thereby exploring their transformative (aesthetic and ethical) effects. Second, it draws a number of connections between Wittgenstein's philosophical exercises and particular aesthetic practices. Third, it sheds light on continuities and discontinuities between Wittgenstein's philosophy and the ancient understanding of philosophy as an exercise and a way of life, so as to sketch out an account of ethics as a practical attitude and way of being. In addition, by including pictures and a text in three different languages, this volume explores new ways of doing philosophy in a Wittgensteinian spirit.