Classroom stories show how using technology to investigate the wage gap provided opportunities to develop students' identities and agency and enabled a classroom culture of sharing and risk-taking. This article illustrates how technology can (a) support students' engagement in case-based reasoning by helping them organize and analyze data; (b) provide opportunities for students to grow in their mathematical understanding, developing mathematical identities and agency in the process; and (c) enable a classroom culture of sharing and risk-taking. The activity highlights how technology empowers students to take charge of their learning, allowing them to choose strategies and representations with which they are comfortable and giving them freedom to experiment with mathematical ideas without fear of having to be "right." Students analyzed the median income of full-time male and female workers aged 15 and older from 1960 to 2020, given by race, education level, and occupation.