Bridging continents and cultures, the Eswatini folktale of Cloud Princess from Africa and the Haudenosaunee folktale of Sky Woman from North America, offer us their shared and relevant wisdom enriching, deepening and expanding our understanding of the meaning of “generosity” in unexpected ways. We learn generosity is the vital and sacred choice that can weave us back into relationship with each other, draw us into closer kinship with the wild, and open ourselves up to belonging to a larger whole.