A growing body of research recognises the underlying complexity in understanding gendered inequalities in development, while there is also a wide consensus that strengthening women’s socioeconomic status leads to better overall markers in education, health, and financial growth. An ethnographic, life course study was conducted within SAHAS India's micro-developmental initiative (to foster financial self-reliance) for women living in the urban slums of the Badarpur Border region in Delhi NCR, which sheds light on the various factors that keep urban poor women in poverty. From situational factors arising out of sociocultural, systemic, and life course-based impediments to their impact on influential psychological factors such as self-confidence and agency, there is a complex of web of entrapment that needs to be unravelled for any developmental endeavour to achieve sustainable upliftment for these women. This chapter advocates for creating small-sized pockets of development as a social revolution in which a participatory, ground-up, hyperlocal, micro-developmental approach not only adapts to the variegated realities of women sub-groups but also inspires investment of time and effort from privileged classes, thus achieving better class integration in society as well.