Our current times are marked by the unprecedented challenges of environmental and social crisis. Transformative changes need to take place and in this study, we explore the role of Gotlandic citizens engaged in sustainability in creating a sustainable future. We follow a recent scholarship focusing on the power of imagination in the context of shaping sustainable futures. Through the theory lens of spaces, we map Gotlandic citizens’ individual experiences of context where they engage with sustainability in different forms of rational and imaginative reflection, alone or together. We conduct qualitative interviews to investigate existing spaces combined with action research where we create a new space of shared imagination in the form of a workshop. An in-depth understanding is gained of the reactions and emotions that our study participants express towards all of these spaces. Going beyond the (k)now, both in the meaning of going beyond traditional forms of knowledge but also in the sense of going into an uncertain future, allowed us to investigate the role of arts-based imagination in the context of an island community. Our findings suggest that spaces for practicing imagination are lacking, but are highly valued when experienced. They provide an alert hopefulness and a gentle way for ordinary citizens to engage with the complex topic of sustainable futures. Another key result of our study is that communities are important spaces where collective visions can grow.