In this episode of PlanningXchange, we speak with Peter O’Leary, whose planning career spans an impressive five decades. Peter began his journey in the mid-1970s as a cadet in local government, rising through the ranks to senior management. He later moved into the private sector before serving over 11 years as a Tribunal Member at VCAT, where he presided over a broad range of planning matters. Following his time on the bench, Peter returned to consultancy, specialising in mediation and dispute resolution. We explore each phase of his remarkable career, drawing on his insights into what makes an effective advocate, a fair and capable decision-maker, and a resilient professional. Peter offers thoughtful guidance for planners at every stage—whether just starting out, navigating mid-career, or reflecting on a lifetime of service. Few reach the milestone of 50 years in the profession—fewer still with such breadth of experience. This is a generous and candid conversation with a true planner’s planner. In Culture Corner / Podcast Extra: * Peter recommends The Incredible Life of Hubert Wilkins: Australia’s Greatest Explorer – Wikipedia – and the documentary Maya and the Wave – mayaandthewave.com. * Jess suggests attending professional conferences for inspiration and renewal. * Pete offers a couple of classic comforts: hot water bottles on cold nights and the contemplative beauty of Evensong at church. Podcast released 26 July 2025