Workers are faced with wider networks of knowledge generation amplified by the scale, diffusion, and critical mass of digital artefacts and web technologies globally. In this study of mobilities of work-learning practices, I draw on sociomaterial theorizing to explore how the work and everyday learning practices of self-employed workers or micro-small business entrepreneurs are changing through the infusion of web and mobile technologies. Drawing primarily on Ingold's notion of wayfinding, Law's collateral realities, and Knorr-Cetina's work on epistemic objects, I examine data from 23 contingent workers in Rwanda, Kenya, and Canada to explore emergent practices of curating learning ecologies (mixtures of technologies, artefacts, activities, and people). I conclude with implications for educators and workers of the growing sophistication of "digital fluencies" that matter: the play of innovation, expertise, and criticality in everyday work-learning practices and a more thoughtful reckoning with the implications of human-technology interactions on practices.