The “smart city” is a set of policies and programs that aim to increase the efficiency and effectiveness of municipal services, encourage urban (re)development, facilitate private investment, and improve quality of life through investing in information and communication technologies. Yet critics contend that the benefits of investment and (re)development programs are not shared equally and there is need for better understanding diverse lived experiences of community members. This paper highlights local voices and lived experiences amid physical and social change in downtown Kitchener, Ontario, Canada, a city that is actively pursuing a smart city agenda. Drawing on data collected from a community workshop that included representatives from local government, technology and start-up sectors, community service providers, and community activists, we adopt a Creative Analytic Practice (CAP) approach and present a set of hybrid vignettes centered on the experiences of these stakeholder groups. The vignettes highlight differing expectations for the role of technology in promoting quality of life and illustrate a struggle to translate aspirations for collaboration and equity into on-the-ground action. We argue that CAP is an effective tool for presenting and enhancing the inclusiveness and accessibility of smart city discussions and debates.