This paper investigates the relationship between personality traits in adolescence and education and labour market choices. In particular, we investigate the impact of locus of control, effort and diligence, and self-esteem, on the risk of youths being unemployed (sometimes referred to as NEET ("Not in Education, Employment or Training"). Thus, our focus is on early drop-out from both education and the labour market at age 18-20. We use matching methods to control for a rich set of adolescent and family characteristics by estimating the treatment effects of multiple personality traits at the same time (Woolridge, 2010). Finally, we use the methodology proposed by Altonji et al. (2005) that involves making hypotheses about the correlation between the unobservables and observables that determine the outcomes and the unobservables that influence personality. Our results show that individuals that display low effort and diligence, low self-esteem, and external locus of control are more likely to drop out of education and employment.