Based on the work of Res et Verba – The Sustainability Network, in many conversations and long walks in the vast forests of the Siegerland (also a form of a philosophical exercise), the authors worked on bringing together the different strands of the current discussion on sustainability with the cultural heritage of Europe. The concept of sustainability and the concept of “Bildung”, a key aspect of this heritage, are inextricably linked: without Bildung no sustainability, without sustainability, no Bildung. This is most clearly illustrated by personal sustainability. Starting from the ancient Greek philosophy, this chapter discusses the qualities of self-guidance, self-knowledge and self-care as the foundation of the good life, leading towards personal sustainability. Philosophical exercises in self-care are presented, raising important questions regarding the individual’s own life practice as well as for persons seeking advice. Essential and timeless aspects of these exercises in self-care include self-receptive, self-reflective, self-productive, therapeutic and ascetic aspects, as well as social, prospective and preventive aspects.