Ecologies of collective imagination involve creating and sharing imagination practice. This modest piece of research engaged 10 artists, environmentalists, and educators to think together about how nature can be a source and a driver of the imagination and sense of possibility for individuals and communities. Together we focused on the concept of re-imagining learning, inside and outside, researching the space of imagination and possibility, nature and well-being for future generations. We explored how collective forms of imagination can engage individuals in actions related to environmental awareness and reparative justice, including ways of widening participation by engaging people who may have been excluded from the power of ecological learning and imagination, ultimately building aspiration and responding to change to build hope for the future. The premise of this project is that human lives are lived in the realm of the possible as much as they are in the here-and-now of immediate experience of the more-than-human world. In this project, we are interested in understanding how we imagine our lives as part of nature, focusing on the question “how can we cultivate an awareness of ‘possible lives’ in ways that respect nature and lead to more hopeful futures?” Our methodology will include opening up spaces for dialogue as a method for the construction of new theoretical and creative methodological tools and processes. This article will consider ecological imagination in the context of art and design education, and creative and eco-pedagogies through a multimodal approach, and a combination of visuals, poetry, and narrative.