Where to Start with Cheryl Strayed: A Reading Guide
Where to start with Cheryl Strayed — whether to begin with Wild, Tiny Beautiful Things, or Brave Enough. A complete reading guide to the memoirist and essayist.
By Natalie Osei
Cheryl Strayed (born 1968) is the American memoirist and essayist whose Wild (2012) — the account of her 1,100-mile solo hike of the Pacific Crest Trail in the months after her mother’s death and her own breakdown — spent more than a year on the New York Times bestseller list and was adapted for a 2014 film with Reese Witherspoon. Strayed is also known for her years as ‘Sugar,’ the anonymous advice columnist for The Rumpus, whose columns were collected in Tiny Beautiful Things (2012) and have been adapted for the stage and television. Her work is characterised by radical honesty about failure, grief, addiction, and recovery, and by a warmth and directness that her enormous readership finds consistently sustaining.
Where to Start: Wild (2012)
The essential Strayed — and one of the most widely read American memoirs of its decade. Strayed is twenty-six years old, divorced, recently clean from heroin, her mother dead for three years. She has destroyed most of what she built. She decides, with almost no planning, to hike the Pacific Crest Trail from the Mojave Desert to Oregon.
The PCT is a thousand miles and three months in her telling. She is not a hiker. Her pack is too heavy to lift without help. She has the wrong boots and no maps and very little money. She starts anyway.
The memoir moves between the trail — vivid, physically specific, full of the particular beauty and misery of extreme effort in wilderness — and the story of what preceded it: her mother Bobbi’s death from cancer, which Strayed describes as the single catastrophic event that began the unravelling. The heroin, the affairs, the divorce — all of it traced back to the loss of the person who made the world make sense.
The trail does not cure her. It is not magic. But it is long enough and hard enough that it requires her to stay present, and presence turns out to be enough, for now.
Tiny Beautiful Things (2012)
Strayed’s collected Sugar columns — advice as memoir, grief as connection. Her most moving work for many readers; the form (responding to others’ pain with her own) allows her a different kind of honesty than the memoir.
Reading Cheryl Strayed
Begin with Wild — it is the essential Strayed and the most complete introduction to her voice. Read Tiny Beautiful Things for her work as Sugar; the two books illuminate each other, showing the same person in different modes.
For the full Cheryl Strayed bibliography, reviews, and biography, visit the Cheryl Strayed author page on Editors Reads.
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Frequently Asked Questions
Where should I start with Cheryl Strayed?
Wild (2012) is the essential starting point — Strayed's memoir about hiking over a thousand miles of the Pacific Crest Trail alone, at twenty-six, after the death of her mother and the dissolution of her marriage and her addiction to heroin. A bestseller for years and adapted for a 2014 film with Reese Witherspoon; one of the defining American hiking memoirs and one of the most honest accounts of grief and self-destruction and tentative recovery available.
What is Wild about?
Wild is structured around Strayed's 1995 hike of the Pacific Crest Trail — from the Mojave Desert to the Oregon/Washington border — which she undertook with almost no preparation, a backpack too heavy to lift, and a determination to do something that would force her to stay alive and present in the world. Interspersed with the hike is the story of what brought her there: her mother's death from cancer, her heroin use, the collapse of her marriage. The trail is both literal and metaphorical; what she finds there is not resolution but endurance.
What is Tiny Beautiful Things about?
Tiny Beautiful Things (2012) is a collection of Strayed's columns as 'Sugar,' the anonymous advice columnist for The Rumpus. Sugar's advice column was distinctive for being personal — she answered letters not with general wisdom but with specific stories from her own life, including her most painful and humiliating experiences. The book collects the most significant columns; it is an unusual hybrid of advice, memoir, and essay, and many readers consider it her most moving work. Adapted for television and stage.
Is Wild suitable for readers who are not hikers?
Wild is not primarily a hiking memoir — the trail is the structure but grief, addiction, and survival are the subject. Most readers who find Wild transformative are not hikers; the appeal is Strayed's unflinching honesty about the specific textures of grief and self-destruction and the specific feeling of doing something hard enough to require your complete attention. The physical details of the trail are vivid but not the point.
