According to Freud, psychoanalysis and education are considered as two impossible professions, both necessarily failing on the rock of castration. At this point the subject has to create an original construct. It is argued that the theoretical concepts good enough mother and true self can be read as the particular constructs of the subject D.W. Winnicott. His particular position towards castration is explored as revealed in the idea of the transitional object. It is not only the content of his work, but, perhaps more importantly, also his style of writing that tries to “hold” the reader. It is precisely in his ideas about a good enough mother/good enough analyst who knows how to hold the child/patient in order to create a true self, that Winnicott’s solution for the impossible professions is found. Psychoanalysis and education are thus conceived of as transforming into another potentially impossible profession: that of creating a desiring subject.