In times of deep crisis, the most powerful critical contemplative pedagogy available to us is that of supporting all children and youth in learning to teach and teaching to learn as a primary path toward self-realization, social inquiry and civic contribution. This vital opportunity should be made accessible to all students, regardless of perceived academic ability, especially to those whose access to voice and to power is limited. In this essay integrating critical, progressive, contemplative and holistic perspectives across time and cultures, I trace the development of a transformative educational philosophy that I will refer to as politically engaged holism. Consistent with this guiding vision, the spiritual dimension of learning and life is acknowledged and fully engaged with careful attention to equity and inclusion. Higher order learning skills promoted via established curricular mandates are expanded to promote development of clarity, communion, creativity and compassion. A corresponding learning process, culminating in empathetic sharing, is engaged alongside traditional learning paths for the purpose of moving beyond contemporary processes emphasizing competitive, standardized individual academic achievement. I advocate requiring (e.g., once/academic year) that all school-age youth be given the opportunity to select a specific concept or skill to teach to others in need (e.g., peers, younger students, family, community members, civic leaders); supported by the level of skilled facilitation necessary to guide young teacher/learners in developing emancipatory learning goals, mastering content, understanding learner characteristics, exploring social pedagogies, receiving feedback, reflecting on implementation and refining practice.