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Prompted by Sigmund Loland's ecosophy of sport and Peter Sloterdijk's analysis of human beings as upward tending training animals, as well as by insights from historical phenomenology (or "metabletics'), hermeneutics, interpretivism and pragmatism, I have argued for a vertically challenged life, preferably to be played out on two unmotorized wheels. Following this plea for cultivating stamina, I ended the previous chapter with an ode to the strenuous mood of the lonely endurance athlete, ahead of the pack, tired but satisfied, and potentially on the brink of the good and flourishing life.Now it is time to return to the overall objective of this study. How can endurance sport at large, and cycling in particular, despite their challenging nature, contribute not only to self-knowledge, but also to self-improvement and sustainability? How to step over from individual metanoia to a collectively (re)introduction of good ecosophical habits? This chapter provides a closer analysis of endurance sport as a preferential contemporary manifestation of askēsis, or training. Once again, but now empirically more fortified, I argue that practiced at your own pace and understood as a process of gradual self-improvement, rather than winning over opponents per se, endurance sport can overcome the stalemate between exclusionary competitive sport and striving for a more inclusionary sustainability. Experiencing and overcoming agony will turn out to be a necessity for the radical change of lifestyle we need.I will concretise and materialise my ecosophical-ascetological stakes and claims by zooming in on specific cases of high suffering in endurance sport. This practical philosophical descent in the pain-cave will result in an illuminating vista on the wider ascetological-ecosophical implications of long distance endurance sport. Agonistic sport and environmental sensitivity, the twain shall meet and merge into a consequential truth that takes a serious effort.

DOI: 10.1007/978-3-030-05294-2_7

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