In this chapter, we write through an academic-arts collaboration, or ‘creative research assemblage’, to explore the dilemmas surrounding cultural representations of women’s experiences of recovery from depression. We focus our discussion on the Mindshackles website that was created by the second author, Iesha, to offer ‘personal stories about reclaiming life from mental ill health’. By documenting diverse stories with photographic images, film, and sound, Mindshackles makes visible the everyday leisure practices that women enact as self-care in recovering their sense of aliveness. We explore feminist questions about how documentary practices can shape digital representations of mental health in ways that both reveal and conceal gender issues.