The concept of solitude has existed in stories and paintings, and in practice, for centuries. Looking at that history, as we do in this chapter, tells us a lot about the preconceptions we have about solitude today – who it’s for, is it positive or negative (or neither), and how we should undertake it. For better or worse, we also see and relate to solitude in part due to the way our various cultures treat it. The images we see and the stories we hear, both historical and contemporary, create chatter that affect how we think about the role solitude can and should have in our daily lives. Shedding light on biases and beliefs fed by historical narratives can help untangle why we approach solitude the way we do today, both as a society and as individuals.