Self-cultivation—taking pedagogical action to educate oneself—is an integral part of non-formal adult education. Ever since Greek antiquity, it has been a central ingredient in the western philosophical and educational tradition. However, we argue that the global challenges that have emerged in the present era of the ecological crisis call for a new kind of understanding of this basic educational phenomenon. Based in particular on recent work in dark ecology and its central concept of the ‘uncanny’, we outline a few key features of our time in relation to the contemporary challenge of self-cultivation. We then review extant literature on self-cultivation to ascertain whether the theoretical resources that have been used to conceptualise it in the past are capable of addressing these new aspects of self-cultivation. We conclude that each of the theoretical resources analysed here offer valuable insights into the novel challenges facing self-cultivation, though not all important questions can be answered. By specifying the contributions and limitations of these theoretical resources, we pave the way for future work on conceptualising self-cultivation for our times.