The moral and ethical charge of teaching and teacher education includes sustaining equanimity and paradox, and maintaining poise amongst contradicting policies and interests. This paper draws upon the wisdom of the Tao Te Ching to address some paradoxes in education and teacher preparation. Specifically, the article looks at four chapters of the Tao Te Ching. By examining these ancient Taoist proverbs from a Western perspective as a teacher and teacher educator in the US this article will discuss challenges and suggestions for teachers and teacher educators successfully navigating amongst, and growing from, paradoxes imbedded in the teaching career.