This paper mainly focuses on two of Shirshendu Mukhopadhyay’s stories and seeks to critique systems of formal pedagogy, and probe the close connections between the child’s psychology and the pedagogic appraisal in the system of formal education; and how this in turn creates the child as a subject, and has a formative influence on him.This paper also analyses the space of the enchanted as one that allows the child to explore vistas beyond the classroom, a site that allows him to confront his “demons” through metaphoric or real ghosts. Set in contemporary society where formal education and its forms of appraisal becomes the yardstick for measuring self worth, failure is a concept that is no longer treated as a space for growth. For the child, the growing pressure and the need to “perform” is not just a metaphoric value judgement, as in both cases of Haribandhu and Burun- it accompanies forms of exile. Exile then is not just a form of punishment; it entails the psychological alienation of the child from the “home”, struggling to reconcile the concepts of failure, filial loyalty and academic progress. Mukhopadhyay in The Ghost of Gosain Bagan and Father Gabriel’s Crypt strongly critiques this sense of progress, and creates an alternate space for the child to rediscover his sense of self.