This article uncovers the intellectual traditions behind Dio Chrysostom's Oration 20: On Anachôrêsis. The examination reveals a variety of subtexts and traditions with which Dio engages, and shows that at its core the text inspects three types of lives promoted by three philosophical schools: Epicurean, Stoic and Peripatetic. They are never referred to directly, however, which raises questions concerning Dio's strategy of not acknowledging the sources of the ideas with which he engages. The article also develops our understanding of anachôrêsis and the controversies surrounding it in pagan antiquity.