This paper uses psychoanalytic ideas to explore obstacles and conditions for learning from experience among teachers. In specific, this is about consequences of failure in relationships. A particular situation that happened during an ethnographic study in a middle school in Norway is used to get as close as possible to a teacher's feelings and perceptions of a frustrating situation. The situation is followed up to understand how the individual teacher tried to deal with the problem and how her colleagues and the school management tried to support and help her. Interpreting the situation to involve violation of all dimensions of the teacher's subjectivity (personal, professional and cultural), the problem seems to be too complex to deal with in the school organization. It seems as if teachers and leadership unconsciously avoid unbearable feelings, with the consequence that violation of the teachers is not recognised, and thus not possible to learn from. Problems were repeated rather than understood.