This investigation explores factors that contributed to the disparate learning identities of two white baby-boomer brothers from the same working-class family. The research, part of a broader phenomenological study into the influences of working-class masculinities and schooling offers an insight into the individual family members' differential communities of practice that over time had the potential to affect each brother's accumulation and utilization of specific forms of social capital. The research challenges conventional thinking regarding the role families play in reproducing educational inequality because it recognizes that an individual's responses to multiple experiences both within and outside the family, rather than family influence alone, are the best means of understanding certain social effects on a student's formal schooling (Goldthorpe, 1983; Phelan, Davidson and Cao, 1991).