Human connection is fundamental for a shift toward sustainable societies. Small groups of people working in response to their unique conditions and environment can find joy in the co-creation of a shared existence. A collaborative network of related efforts can contribute to a broader understanding of resilience and adaptation, aiming toward a regenerative relationship with the Earth and all species. Such an approach ameliorates both pervasive loneliness and extreme inequity that have grown from modern consumerist individualism, through a strong focus on trust, respect and authenticity. I have created a structure to pursue these goals as an applied Sustainability researcher and artist. First, I present a tool that measures and guides community-based work to support the values of equity, justice, transformation and connection. I follow this with an in-depth process of qualitative inquiry grounded in an applied participatory design project to gain insight on the act of building connection across perceived divides. Finally, I share “The Building Community:” the group and process I formed with formerly homeless individuals who are co-designing a tiny home ecovillage of transitional supportive housing for homeless human beings in the Skid Row neighborhood of downtown Los Angeles. The Building Community method combines Council-style talking circles with elements of Action and Design research in which equal co-learners embark on a fun and challenging journey to nurture housing security, interconnectedness, and sustainability. The results of this research indicate an opportunity for community-based researchers to further incorporate support for the rights of nature, decolonization efforts and preservation of the commons into their projects. Flexible structure, consistency, balanced effort and shared decision making proved to build a strong foundation for group processes centered on trust. Finally, The Building Community showed that intimate local groups can produce abundant and creative sustainability solutions when partnered with academic guidance and resources. Sustainability scholars have the chance to balance power, amplify voices and make collective visions manifest if they immerse themselves in efforts on the ground.