This chapter combines postmodern theory, C. G Jung's concept of individuation and Heinz Kohut's notion of self object in an attempt to outline the trajectories of personal evolution in the dynamic and unpredictable world. In post-industrial contexts individuals are responsible for their own development, and they are not expected to rely on community, tradition and ritual for providing them with a sense of identity. Transitions in individuals' lives have always demanded psychic reorganisation, something which was often ritualised in traditional cultures in the shape of rites de passage. Despite psychological fragmentedness being the norm in post-industrial societies, the individual still regards it as unsettling. In the absence of 'instructions', people are left directionless and looking for leaders and role models. Mass media has only replaced the stable, traditional systems that used to provide the individual with identity and belonging. The individual, who longs for the lost communal connection, finds its replacement in mass communications.