This interactive conceptual essay analyzes Glennon Doyle's memoir "Untamed" (2020) to open new possibilities for transformation of the self and consequently as a vehicle to embrace wholehearted living in educational spaces. This article is designed to be read and discussed alongside a trusted educator ally in order to arrive at new understandings, open new dialogues, and unlock new possibilities for wholehearted teaching and learning through a radical togetherness in educational spaces and beyond.