Feminist planning scholars have called for deeper understanding of women’s unique experiences in specific cities. In response, this chapter examines how women in nineteenth- and early twentieth-century urban North America influenced city-building. It specifically reveals how they benefitted from evolving financial and legal tools, along with colonization and the taking of Indigenous lands. It discusses the many legal and social constraints faced by women seeking financial stability. It then illustrates possible ways women responded to opportunities and constraints of the era, through the case of British Columbia settler, Joan Dunsmuir. Joan’s experiences seemed to confirm at least five broader trends impacting women of the era. These included: leveraging the potential for extreme social mobility through colonization; meeting expectations for resilience; directly benefitting from new fiscal and legal tools; exploiting new norms arising in frontier settings; and directly benefitting from Indigenous displacement.