In this chapter, I employ detailed longitudinal questionnaire data from the British Columbia, Canada Paths on Life's Way study to examine the ways in which young people's educational dispositions are constructed and shaped by examining how the parents of my study participants transmitted cultural and social capital to them; how they, in turn, have invested and converted the various forms of capital into educational attainment and occupational status; and how the cumulative impact of these experiences and conditions influence the ways in study participants are currently transmitting cultural and social capital to their children. The 15 year horizon of this study allows for a meaningful examination of the Bourdieu's theoretically rich concepts of habitus and capital, by interrogating the intricate "relationship between the structure of hopes or expectations … and the structure of probabilities which constitute the social space" (Bourdieu, 2000a: 211). Through the method of structural equation modelling, an examination of the long term impact of cultural and social capital on dispositions and value sets of parents are limited at best. Two competing explanations of the results are advanced.