This study supported the emergence of a transformative learning and planning community among marginalized informal settlers in Manila, Philippines. The research was rooted in transformative learning theory while drawing from systems theory, planning, and development participation. We adapted the Search Conference (SC) to examine the process of transformative learning within one community. We customized the SC to local learning styles and culture, incorporating more visual and kinesthetic activities by using participatory development tools. With their involvement in participatory action research, participants drove the process from design, to evaluation, and follow-up through cycles of reflection and action. The findings suggest that a community-driven planning process, undertaken in an environment supportive of transformative learning, can foster meaning making, empowerment, and the emergence of a self-managing group. Our research demonstrated that when people engage in critical systemic thinking about their poverty, this can result in learning and actions that transform their lives.