This chapter investigates the link between uncertainty in the labour market and young adults’ autonomy in Italy and Estonia. It focuses on young adults leaving the parental home and being able to financially provide for their own needs, highlighting the coping strategies youth put in place in different institutional contexts. The results come from a comparative qualitative analysis lasting three years in the frame of the EXCEPT project − Horizon 2020 programme. Evidence from recent research has shown that job insecurity leads to putting off decisions regarding the transition to adult life: postponement of transitions to adult life, non-default transitions order and reversible transitions. Using interviews, we highlight the practical sense of individual actors and the rules that inform their actions. In particular, we show the creative solutions that youth put in place in order to face uncertainty in the labour market. Focusing on subjectivity, it is possible to complete the information on the impact of job insecurity on youth life that emerges from previous quantitative studies. The first consequence of job insecurity, which is having an inadequate income, goes hand in hand with loss of sustainability of household expenses, non-payment of fines and other expenses and over-indebtedness.