This book considers whether and how various philosophies, practices and artworks might help people face, and give new faces to, finitude. Formal education typically emphasizes the journey upward, with ascending and healthy aspects of life like growth and flourishing being common educational aims. However, life also involves downward journeys of illness, decay and death. Written by contributors based in the UK and beyond, the book explores the educational potential in a range of spiritual and social practices as well as examples from cinema and literature that engage with downward journeys. The chapters cover written works by E.M. Forster, Hume, Nietzsche, and Robert Louis Stevenson; films such as Nowhere Special, Toni Erdmann, Terminal Station, The Wild Pear Tree and Dead Poets Society; and social practices and rituals including football. The authors argue that some artworks frame or narrate descent in ways that can educate audiences and reveal the folly in beating wings only upward. Downward journeys show falling or failing and fear of the suffocating dark unknown; but they may also provide glimmers of light, hope and amusement. An education that is full of art and artistry can prepare us to rise and fall, and rise and fall again, not simply to solve or heal, but to be present to what finitude teaches.