Gig economy is presented as disruptive, technologically driven, and forward thinking. Design is explicit in this framing, through use of slick apps to reduce friction and simplify experience for customer and worker. However, this framing is often driven by the platforms, and does not fully recognize the actual experience of work. In this paper we report on a collaborative design process on developing concepts for the future of gig work from a worker-centric perspective. This explicitly does not involve the platforms as stakeholders and uses design fiction as a tool for workers to express fears, joys, and the aspects of their work that are nuanced, reflective and surprising. We reflect on the designs created through this process, the tensions, and opportuni- ties with working with gig working couriers, and issues around power and representa- tion when designing with and for this community.