In this study, we discuss the relationships between the private and professional life of male managers, with special emphasis on the meaning of fatherhood in this relationship. By presenting and studying the symbolics of an adventure movie, Hook, we aim to show how the personality of a male manager named Peter Banning is changed when he grows closer to his children through recalling his earlier life as Peter Pan, a boy with a rich fantasy life and the ability to fly. The key concepts in our interpretation are drawn from clinical approaches toward management, narcissism in particular. Moreover, we aim to point out that managerial personality issues are closely related to the questions of gender and to the reconstruction of masculinity as a social trend. Until now this aspect has not been considered in management studies applying the clinical approach.