Grief and the Decision to Hike
Cheryl Strayed stood on a steep California mountainside when her heavy hiking boot accidentally tumbled over a rocky ledge, disappearing into the vast forest below. Left with only the matching boot, she realized the single shoe was useless and threw it after its partner. At twenty-six, she felt as orphaned and adrift as those boots. Her mother’s death years earlier had shattered her family, her father was long gone, her siblings had scattered in their grief, and her marriage had ended in divorce. After years of reckless behavior and searching for meaning, she decided to hike the Pacific Crest Trail to find the person she used to be. The trail is a 2,600-mile wilderness path stretching from Mexico to Canada.
The true beginning of her journey started years earlier in a small clinic room when she learned her mother was dying. At twenty-two, Cheryl listened to a doctor explain that her vibrant, forty-five-year-old mother had late-stage lung cancer. The news was a physical blow that shattered the belief that a healthy lifestyle could prevent a terminal diagnosis. Her mother, Bobbi, had escaped an abusive marriage and raised three children in poverty, relying on a fierce optimism that served as the foundation of their family. The promised year of life rapidly dwindled to weeks, and Cheryl became her mother’s primary caregiver until she passed away.
The years following the death were marked by a profound unraveling. Cheryl was haunted by recurring dreams and overwhelming guilt over her inability to save her mother. Her marriage to a kind man named Paul began to disintegrate because she could no longer connect to his stable life. She sabotaged their bond with a string of impulsive affairs, driven by a self-destructive urge to cure herself of her own pain through reckless intimacy. She eventually spiraled into an addiction to heroin, which provided a temporary escape but left her with a crushing sense of shame.
A positive pregnancy test and the memory of a trail guidebook she had seen in a store acted as a catalyst for change. She realized she needed to return to the responsible, ethical person she had once been before her mother died. By the time Cheryl arrived at a dusty motel in Mojave, California, to begin her hike, she had stripped her life down to the essentials. She finalized her divorce, ended her pregnancy, and packed her belongings into boxes to be mailed to remote trail outposts. Standing in a cheap motel room dressed in brand-new hiking gear, she confronted the reality that she had never actually gone backpacking in her life.



