Hermann Hesse (1877–1962), the poet, novelist, man of letters, and painter, created characters who, like the Daoist sages, had many paradoxical characteristics. Some of Hesse’s characters manage their paradoxical natures well and, like the balanced sages, are able to be simultaneously changing yet stable, full of life but also empty, in unison with nature and the social world. Centered between interchanging extremes, these balanced individuals are carefree yet self-controlled, efficacious in their work yet seemingly inactive, and successful in sustaining leadership (...) and power yet humble and non-obtrusive. These sage-like individuals, the ideal leaders presented in the Daodejing 道德經, will be the focus of this essay. Specifically, I will focus on the Daoist hub and wheel analogy, the concepts of wu 無 and you 有, absence and presence respectively, which are extremely important in order to understand the influence of Daoist philosophy on Hesse’s literary examples of sage-leadership. (shrink)