This paper focuses on parents and the way they perceive and formulate expectations and aspirations about their children's educational and occupational outcomes. Drawing on evidence from a survey among more than 700 parents of primary school pupils this paper demonstrates that interesting patterns in parental aspirations can be observed. These patterns can be partly explained by differences in parental social and cultural capital circulating in the home environment. The discussion of the results evolves around the argument that families often employ different strategies as a result of their social positioning which relates to particular social and cultural characteristics that shape distinct "habituses" of either success or compromise. This paper contributes to the examination of the often hidden mechanisms that originate from the family and produce social class differentiation in education that sustains overall social inequalities in contemporary Greek society and makes the ideal of equity in and through education still illusive. (Contains 8 tables.)