Fighting illness could be a nonsense, if we consider human condition as a disease in itself. This paper shows that, in Montaigne’s skeptical anthropology, firstly health can be considered as an adjustment of disease, and therapeutic obstinacy as a pathological refusal of self; secondly that the healthy acceptance of oneself as sick differs from Stanley Cavell’s interpretation of skepticism, based on Descartes’ work, as pathological obstinacy to cure humans of their contingency.