This article introduces an interdisciplinary collaboration that brings together sympathetic trends in qualitative geographic visualization (from the perspective of one author who is a geographer) and contemporary generative artistic practices (from the perspective of the other author, who is an artist and theorist)—attempting to represent a diverse array of creative and multi-modal data through generative and participatory digital methods. We present how this convergence expands categories of meaning, allowing us to explore experiential/embodied as well as creative/imaginative engagements with everyday geographies distinct to a digital age. The article mediates on the idea of mapping the imagination and the ways we imagine quotidian spaces, as well as possibilities for new methods for the analysis and representation of spatial and emotional complexity. We particularly explore strategies of integrating multiple technologies and multiple-modes of representation for mapping and re-mapping complexities of social and creative living in order to help provide alternate ways to imagine, represent and engage different forms of embodied and imaginative geographies. This article presents a case study with the artist Andrew Buckles, in Seattle, Washington, correlating representational and participatory digital data including geospatial, temporal, audio, video as well as electroencephalography readings from brainwave sensors.