For many students, especially minority and low income students, attending college is a genuinely desired but elusive goal. Research on aspirations and expectations may provide a way to understand the gap between what students' desire and what they actually expect to happen. This set of studies moves toward providing a conceptual framework for understanding how expectations are formed and how they can be influenced. Students' saving for future schooling (SFS) is examined as a way to reduce the gap between aspirations and expectations among disadvantaged students in the set of related studies examined in this dissertation. I find that among students without savings for future schooling there is an aspirations/expectations gap of 41 percentage points. In contrast, there is an aspirations/expectations gap of only 12 percentage points among students with savings for future schooling. Students with savings for future schooling are nearly twice as likely to expect to attend college as students without savings for future schooling when controlling for parent, student, psychological, academic and economic controls. It may be that when the financing of college is perceived as being under student's control, college attendance becomes more of a reality for some students. Students with savings for future schooling are not only more likely to expect to attend college, they perform better in school. Math scores of students who have savings for future schooling score 4.57 points higher than children who do not have savings for future school. Students with savings for future schooling are nearly twice as likely to be enrolled in college as students without savings for future schooling. Moreover, findings indicate that students' college expectations act as a partial mediator between SFS and students' math achievement, and SFS and students' college enrollment. In addition to examining the role of SFS, this set of studies also examines the role of parental savings for future schooling (SFC). SFC is associated with an increase in parent expectations. However, SFC is not statistically significant with either children's math achievement or students' college enrollment. It may be that SFS are a more effective policy solution for increasing students' academic attainment.