The field of youth sociology has been challenged to reconsider the role of parenting in the lives of young adults. This paper presents a multiple-case study investigation into young men’s transitions from school into further education in an Australian context. We will argue that relationships with parents are materially, socially and emotionally salient throughout the period during which young men move out of adolescence and into young adulthood during their final year of senior schooling and beyond. In considering how the young men constituted their identities in the context of family relationships, we will highlight the dynamic interplay between three relational identities: dependent, independent and interdependent. We show that a main locus of tension was the negotiation of power and agency in the representation of self in relation to parents, specifically in the context of a period in which educational achievement was highly emphasised.