Colonial institutions, such as residential schools, suppressed First Nations peoples’ imaginations, punishing those who sought to exercise their imaginations. Creating imaginary spaces is an important aspect of the process of decolonization and includes the reclamation of traditional modes of relationships in new forms, the co-creation of new possibilities, and the transformation of political and personal histories. In this article, we describe a workshop with First Nations youth, focusing on two arts-based activities used to evoke imaginative spaces for First Nations youth to explore, critique, and re-imagine their histories, current realities, and futures in a safe and comfortable environment. The process of imagery and imagining facilitated awareness of things not easily expressed in words as youths’ imaginative ideas emerged through their drawings. Through these activities, youth expressed their view of healthy communities that included cultural traditions and leadership. They described leadership as enacting good communication, organization, protection, and maintenance of cultural traditions, as well as providing guidance and defending the rights of the community. These imagined possibilities provided meaningful blueprints that youth can use, alter, and be inspired by as they move towards being leaders of healthy communities.