This dialogue presents a weaving together of themes embodied in the work of Nina Simons, co-founder of the non-profit Bioneers and women's leadership author/speaker, and Anneke Campbell, writer, health educator and community activist. Starting from the premise that our current crises are based in embedded cultural biases toward separation, they explore how their divergent life experiences inform how we might address our societal ruptures by helping to create connective tissue within ourselves, and among groups and movements. They examine some practices we could cultivate to center ourselves and support others through the discomfort and uncertainty that ensues from addressing our personal and systemic challenges and divisions. Touched upon in their discussion are outdated or patriarchal ideas of what leadership is, re-imagining a more holistic approach to leading based in love, connection, and embodiment, and the use of ritual to reconnect us to each other and to the better angels of our nature. Their conversational approach is emblematic of the recognition that all life, leadership, and learning are sourced in relationship.