Sixteenth-century French philosopher Michel de Montaigne was one of the first writers to reflect on embodiment. “I am myself the matter of my book,” he proclaims in the introduction to his Essays. Montaigne writes about various moments of embodied transitions: a near-death experience, reflections on aging and cognitive decline, and a lengthy discussion of how to cope in the face of devastating loss. Taking an interdisciplinary perspective by analyzing the relationship between embodiment, health representations, and geropsychological themes, this chapter analyzes Montaigne’s in-between moments, arguing that Montaigne’s essays—innovative in their own time—remain important in discussing embodied transitions today.