This chapter’s exploration of the concept of insight focuses on the intersection of personhood and ideas about knowledge in literature and the arts. What are we? We are those who can be struck by something in an aesthetic encounter. We are those who are susceptible to insight. For in encounters with aesthetic works, something often comes to be illuminated, and we see something anew. In addition to doing all of the things we are told works of literature and art do (inspire us, perplex us, amaze us, disgust us, educate us), they also hook onto the world and give us insight into real things. What does this capacity to be struck by insight bespeak about the shape of the capacities of persons? What do works of literature and art have to teach us? How can we think about literature as “saying something” without reducing it to easy morals or broad truth claims? These are the questions that structure this series of reflections on the concept of insight. This chapter explores works by Plato, Friedrich Schlegel, Jane Austen, Friedrich Nietzsche, Henrik Ibsen, Virginia Woolf, Ludwig Wittgenstein, and Samuel Beckett.