Trends towards unsustainability are worsening, driving interest in inner transformation to support progress towards a more viable and just future. Many approaches to these transformations include interventions intended to shift ways of seeing, being, and relating in the world from a narrative of separation towards one of interconnectedness. Transforming dominant systems that perpetuate inequities and imperil both social and ecological systems is a necessary yet profoundly challenging task. This paper synthesizes the dialogue between four individuals with diverse backgrounds in inner transformation, sustainability, and systemic change hosted by the Transformations Community at the annual 2023 conference. Diverse approaches to and cautions for shifting mindsets towards more sustainable worldviews were discussed. Emergent insights from the discussion inform a growing body of scholarship and practice at the nexus of inner and outer sustainability.