In March 2023, RHJ editors Melissa Fernández Arrigoitia and Mara Ferreri had a long online chat with Allan D. Heskin on his life and committed work linking community advocacy, housing organizing and planning scholarship, as collected in books such as The Struggle for Community (1991). This is an edited, re-ordered version of that conversation. It contains some conversational references to Allan’s work, which may read as gaps in the structure but rather than explaining things in smoothed detail, we invite readers to delve into the rich material Allan has written. We cannot overstate the value of his ethnographic analysis and planning perspectives.