Research investigating the effect of working mother's increasing involvement in multiple domains of life typically assumes that negative experiences from work and family domains accumulate to detrimentally affect well-being (Tingey, Kinger, & Riley, 1996). The aim of the present study was to investigate how working mothers' positive and negative experiences across multiple roles (e.g. work, home, sport, religion) interact to have cumulative, compensatory or segmented influences on their well-being. The lack of existing literature in this area and the need to accommodate a comprehensive conceptualisation of working mothers' multifaceted life experiences necessitated a qualitative process of analysis. Using a social constructionist epistemology data was obtained from individual, semi-structured interviews with 22 working mothers from four organisations across Tasmania and Victoria. Interviews were analysed according to the principles of Braun and Clark's (2006) six-phase thematic analysis process. Findings revealed that working mother's well-being was influenced by an association between their Type A or Type B personality characteristics and interpersonal relationship conflict or satisfaction. Results further identified that these constructs mediated, or were mediated by working mothers' cumulative, compensatory or segmented experiences across work, home, social and personal roles. The implications of these findings for theory development and intervention design are discussed.