Drawing from ethnographic research on Canadian people living off-grid we describe and interpret how people without formal training in architecture or construction manage to build their own homes. Our findings show that they do so thanks to what we call regenerative life skills. Juxtaposing our argument in the context of DIY (do-it-yourself) research and discourse we argue that rather than in a solo endeavor off-grid builders engage in relational practices, becoming entangled with others, with historical traditions, with place-specific resources, and with the affordances of the materials they utilize. DIW (do-it-with) relies on the engagement of what we call regenerative life skills – drawing from relational theory and regenerative design.