This article explores the affective dimensions of disabled, D/deaf, mad, and neurodiverse artists’ work through a livelihoods framework informed by the social and tacit dimensions of heartbreak. Heartbreak emerged during interviews with twenty artists in Canada in 2020, during a time of significant state- based policy changes that impacted disabled people’s livelihoods in the province of Ontario. Taken together, the artists’ stories form a rhizomatic cartography that takes crip wisdom and desire as significant elements of artmaking amid wider relational assemblages of affect. Drawing on Deleuzian and Guattarian concepts of desire and Puar’s difference-in/as-assemblage, researchers assert that although crip artmaking is not without joy, heartbreak is embedded in the politically aesthetic work of cultural production.