What is transformative insight, what methods lead to it, and what results come from it? Beyond short term benefits, lasting transformation from contemplative practice appears to come from shifts in the way practitioners see themselves, their experiences, their world, and others. Has the time come for a broader approach to contemplative practice, one that builds off of popular practices like mindfulness, attention training, open monitoring, and loving kindness, but that taps into our relationality to bring in forgiveness, gratitude, interdependence, mutual respect, humility, and common humanity through a fuller recognition of ourselves as social beings, not isolated practitioners? From a research perspective, are we ready to evaluate not just the individual health and psychological benefits of contemplative practice, but the quality, quantity and sustainability of transformative insights? One such method is self-examination through the eyes of others, as done in the Japanese practice of Naikan. At the intersection of therapy and meditation, this deceptively simple practice involves asking only three questions: “What have I received? What have I given back? What trouble have I caused?” It requires individuals to look at their past from the perspectives of others in their life, resulting in a confrontation with interdependence, one’s own and others’ fragility, and the system dynamics that have shaped and continue to shape one’s life. This approach to transformative insight hits both self-cherishing and the natural sense to see oneself as a self-made, self-sufficient individual, and invites us to develop a more comprehensive and expansive approach to contemplative practice.