In contemporary times, issues around womanhood and gender are very much part of the social, political discourses and form a burgeoning area of research as well. The media images of the empowered working women and happy homemakers reinforce images of efficiency and effectiveness in respective roles. Some valuable work has been done in the area of work life balance, however more needs to be understood about the narrative and life of the ‘person’ beyond the various roles. The present study explores issues related to the ‘making of the self’ , the ways and patterns of negotiating with different life worlds especially in case of working women, understanding the psychological challenges and channelizing of ‘ ambition’ among homemakers. Lastly, do both perceive one another as the ‘other’? Data was collected though in-depth interviews of 10 married female participants and analyzed based on Thematic Network Analysis. Some preliminary trends in data analysis revealed a sense of loss in relationships, in the need to maintain the structural requirements of family life, a vicious cycle of being perfect leading to unwarranted anxieties and sense of inadequate self. The study has implications for highlighting some of the relational dimensions that need to be addressed for a sense of well being among Indian women.