Background: The economic downturn combined with the ongoing process of target segmentation of the work force have made increasingly difficult the access and the integration of young people in the labour market. A general worsening of job quality and under-qualification practises for new entrants are amongst the most marked features. Italian and French comparison shows how conjectural and structural factors force them to face precariousness with strategies based on personalised trajectories. Objective: The study aims at showing how precariousness affect youth careers and which dynamics they activate to achieve professional and personal expectations. We plan to explain how job precarity and life uncertainty concern subjective dimension, which depends on both socio-demographic characteristics and temporal-geographical perspective. Method: We shall investigate youth employment conditions through standardized dimensions and subjective perceptions. Cross-sectional analysis based on European Union Statistics on Income and Living Conditions will provide quantitative analysis. The qualitative analysis based on semi-structured interviews of Italian and French people aged 20-35 having different levels of education, social origin and gender. Results: In Italy and France, both the level of education and familial background occurred to explain intergenerational inequalities in work trajectories. In both countries, women are more educated and look for fulfilling jobs. They are more likely to use training to keep developing their abilities and accept temporary jobs. Men suffer more the lack of job continuity and perceive spells in unemployment like a personal defeat. They are oriented to economic satisfaction around their thirties. Active policies are factors boosting job attachment although widespread disaffiliation feelings, which are more evident among youth from lower social classes and living in the Southern regions of both countries. Conclusion: Because of job precariousness and life uncertainty young people develop individual mechanisms to achieve a compromise between creative dynamic work search and passive acceptation of job precariousness.