This paper uses an innovative survey instrument on employment and earnings quantitative expectations to measure the amount of job instability, insecurity, and earnings risk that jobless young skilled perceive. The survey was fielded in Italy, as one of the EU countries that suffered the highest increase in youth unemployment, and the data were merged with administrative records on local labor market conditions. The results show that Italian jobless young skilled perceive substantial job instability, insecurity and earnings risk, which correlate with several important choices and behaviors, and depend on individual characteristics rather than on local labor market conditions.