The article provides an example of psycho-societal analysis of work related learning. Initially a conceptual framework of learning and life experience is established drawing on Alfred Lorenzer and Oskar Negt, and the interactional development of psychoanalysis. A case of learning experience from research into a retraining program for unskilled workers, exposing a very conflictual subjective experience of a traineeship, is presented and commented. The worker's experience is interpreted focusing on the gender aspects of the conflicts, seeing the learning process in the context of a work identity process, which is related to a career shift enforced by labor market transition requiring male workers to retrain for a social work profession which used to be female, and more widely to a reconfiguration of the societal relation between work and gender. The final section discusses the methodological framework for analyzing learning processes by means of interpreting language use. The notion of language game connects the level of unconscious social engagements and level of formal learning and knowledge, and the opportunity for a deeper understanding of professional learning and identity is indicated by reference to one more example.