Patterns of transition to adulthood are conceptualised in terms of three dimensions encompassing contradictory principles: the social definition of youth (consistent/inconsistent), the structure of social relations (hierarchical/symmetrical), and behavioural orientations (conformity/deviation). We apply this conceptualisation to a comparative analysis of transition to adulthood in Israel during two distinct historical periods: the 1950s (`transitional society') and the 1980s (`post-transitional society'), studying the link between macro-social conditions and transition anchored in the life-cycle of the individual. The research entails a structured content analysis of articles appearing in an Israeli newspaper for youth during the two periods, where the unit of analysis is roles. The findings indicate two different, yet non-polar patterns of transition: `Transitional society' is characterised by the coexistence of contradictory principles related to a strongly ambivalent attitude toward youth. `Post-transitional society' shows fewer coexisting contradictions due to a reduced reliance on youth and an ability to absorb loose behaviour.