This volume is an examination of human wisdom in a variety of contexts dealing with memory, free will the human heart, mortality, the self in love, and contemporary American politics. It contains reflections that arise at the intersection of five domains of knowledge: literature, philosophy, psychology, recent neuroscience, and pop culture (music and film). More than six decades of reading, thinking, and living culminate here in a belief that change and learning are the beating heart of human existence and an agnosticism with an upside. The ability to doubt received knowledge, while critical, is only one component of wisdom. The truly wise person has also learned to be cautiously skeptical about skepticism itself. In this way the person not only avoids premature closure on possibilities that might become real but may become more tolerant of other, competing views, as long as these are not dogmatic or hurtful. When circumstances require it, humans can live in a cognitive gap and still be wise.