Adolescent period is a threshold where play and what is infantile is left behind. Instead, phantasy takes place and creativity is experienced. This experience involves adolescent’s awareness of possessing a body and a psyche which has the capacity to produce, reproduce. It also includes fragile and naive parts of adolescence as a period of change, and transformation. Thus it is important to look at what Hanna Segal has said regarding creativity and art, in order to understand how during adolescence, creativity is closely linked with separation, mourning and depression. Catcher in the Rye which was published in 1951 is worth examining as it both brings us closer to the world of an adolescent and also in relation to the author’s narration of his own creativity.