Founding, running, maintaining...conferences! What does it mean to maintain a conference? What does it mean to the organizers, and also the community it benefited, to retire one? Different geographies and cultures allow for experimentation, risks, failures and successes on the human-centered projects that Catherine Lopez and Tracy Hinds have been working on for years. An ever-expanding story of growing more caring communities through the trials and tribulations of A/B testing experiences within Cascadia, EmpireJS/Node, JSConfCO, ScaleConf, and code project communities such as Node.js.