Margaret O’Brien lives in a heritage property in Fitzroy. She has been confronted by the frailty and the essentiality of heritage and its dependence on others for recognition and survival. But communities, on the outside of the heritage systems, often have different perspectives from those on the inside, making the decisions. What seem missing are the effective connections between the outsiders and the insiders, the community and the controllers. This paper is part of the quest to better understand how to collectively work for the future of heritage.