Efforts toward social progress and sustainability in organizations and communities often face a problem of “preaching to the choir” – a stark division between people concerned about social change and those with other concerns top of mind. To achieve the resilient systemic change we claim we desire, movements for sustainability, social justice, and public health require conversation across diverse perspectives, ideologies, and personal backgrounds. How do we build this broader movement? The answer lies in having authentic, effective, one-on-one conversations about the things that matter, capable of inspiring and empowering others to join in the pursuit. But this is not always easy. As advocates, we often find ourselves in a condition of polarization and gridlock, a microcosm of the larger challenge on the political stage. This workshop guides participants through an exploration of the idea that such gridlock occurs when we harbor hidden commitments to being right, righteous, certain, and safe at the expense of being effective. The goal, and central theme, of this workshop is to develop participant’s awareness, such that they are able to identify pitfalls in their own life, real time, and are empowered to create new pathways forward. Pathways lead to greater authenticity and effectiveness, and contribute toward a transformation of movements  to engage wider constituencies, and support the flourishing of our lives in the pursuit of the flourishing of all life.