This paper deals with illness and difficulties at work for secondary school teachers in the French educational system. Based on a qualitative approach, using interviews and the records of a help device for teachers, it shows that there are several levels at which unease is manifested, particularly at the intersection of individual modes of thought and organizational constraints. The aim of this paper is to understand such teaching difficulties, from their realization to resignation from teaching. The study shows the formation of painful personal paths which lead to “deviant” careers and for some, professional dropout, latent or real.