Starting with an argument for a humanistic approach to climate change, this paper discusses the concept of the ‘Collective Artist Residency’ as a practicable means for engaging with complex socio-ecological issues that require collective answers. Through our analysis of the research project ‘Imaginative Disruptions,’ we propose that there is a need for creative spaces that include artists and non-artists alike, and which engender aimless play, inquisitive making and dialogic contemplation in the face of issues which are too painful, overwhelming and complex to rationally comprehend. We further argue that such residencies can generate comfortable, and even light-hearted, spaces in which people can be uncomfortable together. In other words, environments that feel safe and caring but that also encourage us to challenge status quos and experiment with alternatives via emotional, aesthetic, cognitive, somatic and social processing. The paper closes with five (suggested) guiding principles for designing a Collective Art Residency that supports groups of people to co-reflect upon their fragility whilst re-imagining present and future possibilities for being in the world: deeply participatory, balanced between comfortable / uncomfortable emotions, highly experiential, cross-sectoral and intergenerational, place-based.