The dominant 21st-century worldview is replete with stupid rather than wise values, signified by corporate greed, climate crises, environmental degradation and huge economic disparity. Is this what we want for our children and their grandchildren? What do we aspire towards? After a brief diagnostic, I reiterate the evolution of consciousness theme, the postformal qualities and the postformal pedagogies that I conceptually weave into my tapestry of wisdom. The main sections of this chapter explore the philosophical importance of wisdom, educational approaches that encourage and support it, many practical examples from educators of how to cultivate wisdom and some personal reflections on how I have worked creatively, complexly and multi-modally in my educational endeavours.