Despite widespread interest in the changing technologies, economies and politics of creative labour, much of the recent cultural production scholarship overlooks the social positioning of gender. This article draws upon in-depth interviews with 18 participants in highly feminized sites of digital cultural production (e.g. fashion, beauty and retail) to examine how they articulate and derive value from their passionate activities. I argue that the discourses of authenticity, community building and brand devotion that they draw on are symptomatic of a highly gendered, forward-looking and entrepreneurial enactment of creativity that I term ‘aspirational labour’. Aspirational labourers pursue productive activities that hold the promise of social and economic capital; yet the reward system for these aspirants is highly uneven. Indeed, while a select few may realize their professional goals – namely to get paid doing what they love – this worker ideology obscures problematic constructions of gender and class subjectivities.