This qualitative study explores the psychological and social processes underlying the issue of generational transmission of coloured identity within the South African contexts of colonialism (pre-apartheid), apartheid and democracy. The concept of identity was guided by the theoretical approaches of Object Relations and the reflexive project of the self to further explore the lived experience and transmission of this identity. The lived experience of coloured identity of four generations of women within one family was examined. The four women ranging in age from 89 years to 23 years participated in individual semi-structured interviews. The data was thematically analysed. The major themes highlighted were: the interaction of personal identity and social identity; the politics of power and control on identity; the influence of socialization on issues of gender and culture; shifts or changes in identity within a generation or trans-generationally; and the generational transmissions in the reflexive project of the self. This study illustrates the challenges facing individuals, particularly women, with contested identities of marginalized groups. It provided insight into the underlying feelings of trust, shame, pride and guilt as these women negotiate the changing socio-political landscape of their country. It also explores the challenges of dual roles of insider and researcher / Thesis (M.A.)-University of KwaZulu-Natal, 2008.