In 2023, against the backdrop of alternative facts, deep fakes, and artificial intelligence, Merriam Webster named 'authenticity' as its word of the year. In "Philosophical Investigations," Wittgenstein asks people to understand that words assume meaning within forms of life and bear family resemblances to kindred words. While resembling words such as 'reality', 'truth', and 'integrity', authenticity also entails agency--the capacity to evaluate, imagine, and create. Conversely, and resembling words such as 'fake', 'phony', and 'synthetic', inauthenticity entails predictability, conformity, and vacuity. As humanity careens further into climate crisis and authoritarianism, the ability to resist inertia, change course, and generate novelty appears both tenuous and indispensable. Searching for wisdom to guide, this essay investigates currents of thought and culture that have both promoted and discouraged human agency. Connecting historical, philosophical, and anthropological perspectives, the authors consider possibilities for bringing education into closer alignment with the ethic of authenticity.