What does psychoanalytic theory and experience suggest about the advisability of going “gentle” into the “good night” that awaits us? This chapter considers the opinions of poets, clinicians, fiction writers, and others. For some, a central challenge in aging is preserving a relatively unchanged identity, while others view aging as potentially freeing us from the constraints we previously accepted. Some issues considered include shame and disgust about aging and defensive patterns that color the experience of growing older.