William James was one of the most influential American psychologists and philosophers. His writings remain thought-provoking and relevant more than a century after his death. His seminal ideas range from free will, determinism, the nature of consciousness, the mechanisms responsible for our emotions, religious and spiritual experiences, psychic phenomena, and the veracity of mediumship. This chapter focuses on what is less well known, that behind the appearance of success he lived a life burdened with recurrent depression, hypochondria, and myriad physical afflictions, most of them psychosomatic in nature. His search for a career path was long and torturous. At different stages in his life, he was a frustrated artist, a reluctant physician, and a drifter. He found his calling in teaching. His lifelong search for the nature of the mind and the soul was deeply entangled with his father’s, whose tragic and accidental loss of a leg in childhood led to a relentless lifelong quest for “real” answers. The chapter also touches on Ralph Waldo Emerson, his godfather, and includes brief descriptions of William James’ famed novelist brother, Henry James, Jr., as well as his sister, Alice James, the brilliant reclusive diarist.