Parents and their children's expectations on educational achievement have been highlighted in the literature as proper proxy indicators for students' forthcoming performance. In this research we intend to measure the effect of these indicators accounting for the existence of endogeneity-due to their reciprocal relationshipand also their correlation with unobservable variables conditioning students' achievement. The aim is to determine the extent to which the potential positive correlation between expectations and children's educational performance could help to overcome the limiting effect of low socio-economic characteristics of the household on the latter and, consequently, the well-being of children in the medium and long run. Our results show a positive influence of the agreement of parental and children's expectations on students' achievement and on the likelihood of children's enrollment in a particular academic track. In addition, parental expectations have been found to be dependent on family socio-economic background, what supports the persistence of strong barriers to socioeconomic mobility of children. We suggest policy interventions as, e.g., fostering the participation of both parents and children on university and professional orientation in early stages of secondary education, so they could have complete and symmetric information to set their expectations on a realistic basis.