In 1986, at the age of 17, Strayed graduated from McGregor High School in McGregor, Minnesota, where she was a track and cross country runner, cheerleader, and homecoming queen. In 1987, during the summer after her freshman year of college, Strayed worked as a newspaper reporter for her hometown county weekly, The Aitkin Independent Age in Aitkin, Minnesota. She loosely based the fictional Coltrap County in her novel Torch on McGregor and Aitkin County. Strayed attended her freshman year of college at the University of St. Thomas in Saint Paul, but by her sophomore year, she transferred to the University of Minnesota in Minneapolis, where she received her Bachelor of Arts degree, graduating magna cum laude with a double major in English and Women’s Studies. In March 1991, when Strayed was a senior in college, her mother, Bobbi Lambrecht, died suddenly of lung cancer at the age of 45. Strayed has described this loss as her “genesis story”. She has written about her mother’s death and her grief in each of her books and several of her essays.

Strayed married Marco Littig in August 1988, a month before her 20th birthday. They divorced in 1995, shortly before she started hiking the Pacific Crest Trail.

Her memoir Wild: From Lost to Found on the Pacific Crest Trail details her 1,100-mile hike in 1995 on the Pacific Crest Trail from the Mojave Desert to the Oregon–Washington state line and tells the story of the personal struggles that compelled her to take the hike. Three months before her memoir was published, actress Reese Witherspoon optioned it for her company, Pacific Standard. Nick Hornby adapted Wild for the screen, with Witherspoon portraying Strayed in the film.

Strayed subsequently married filmmaker Brian Lindstrom in August 1999. They have two children and live in east Portland, Oregon, where Strayed has lived since the mid-1990s. Her daughter, Bobbi Strayed Lindstrom, played the younger version of Strayed in the film adaptation of Wild.

In addition to her four books Wild, Tiny Beautiful Things, Brave Enough, and Torch, Strayed has published essays in various magazines, including The Washington Post Magazine, The New York Times Magazine, Vogue, Tin House, The Missouri Review, and The Sun Magazine. Her work has been selected three times for inclusion in The Best American Essays (“Heroin/e” in the 2000 edition, and “The Love of My Life” in the 2003 edition, and “My Uniform” in the 2015 edition). Strayed was the guest editor of The Best American Essays 2013 and The Best American Travel Writing 2018. She won a Pushcart Prize for her essay “Munro Country,” which was originally published in The Missouri Review. The essay is about a letter Strayed received from Alice Munro when she was a young writer, and Munro’s influence on Strayed’s writing.

Strayed worked as a waitress, youth advocate, political organizer, temporary office employee, and emergency medical technician throughout her 20s and early 30s, while writing and often traveling around the United States. In 2002, she earned a Master of Fine Arts in fiction writing from Syracuse University, where she was mentored by writers George Saunders, Arthur Flowers, Mary Gaitskill, and Mary Caponegro.

Strayed’s first book, the novel Torch, was published by Houghton Mifflin Harcourt in February 2006 to positive critical reviews. Torch was a finalist for the Great Lakes Book Award and selected by The Oregonian as one of the top ten books of 2006 by writers living in the Pacific Northwest. In October 2012, Torch was re-issued by Vintage Books with a new introduction by Strayed.

Strayed wrote the popular advice column “Dear Sugar” on The Rumpus. She began writing the column in March 2010, when the column’s originator Steve Almond asked her to take over for him. She wrote the column anonymously until February 14, 2012, when she revealed her identity as “Sugar” at a “Coming Out Party” hosted by the Rumpus at the Verdi Club in San Francisco. A selection of her columns has been collected in her bestselling book Tiny Beautiful Things.

Strayed’s second book, the memoir Wild: From Lost to Found on the Pacific Crest Trail, was published in the United States by Alfred A. Knopf on March 20, 2012. It has been translated into 37 languages. The week of its publication, Wild debuted at number 7 on the New York Times Best Seller list in hardcover non-fiction. In June 2012, Oprah Winfrey announced that Wild was her first selection for her new Oprah’s Book Club 2.0. The next month Wild reached number 1 on the New York Times Best Seller list, a spot it held for seven consecutive weeks. The paperback edition of Wild, published by Vintage Books in March 2013, spent 126 weeks on the New York Times Best Seller list. The book has also been a bestseller around the world—in the UK, Germany, Australia, Brazil, Spain, Portugal, Denmark and elsewhere. Wild won the Barnes & Noble Discover Award and the Oregon Book Award.

In July 2012, Vintage Books published Strayed’s third book: Tiny Beautiful Things: Advice on Love and Life from Dear Sugar. The book debuted in the advice and self-help category on the New York Times Best Seller list at number 5 and it has also been published internationally. Tiny Beautiful Things is a selection of Strayed’s popular “Dear Sugar” advice columns, which she wrote for no pay for the literary website The Rumpus from 2010 to 2012.

In June 2012, Wild was chosen as the inaugural selection for Oprah’s Book Club 2.0, which is a relaunch of Oprah’s Book Club, which ended in 2011. Winfrey discussed Wild in her video announcement of the new club and interviewed Strayed for a two-hour broadcast of her show Super Soul Sunday on her OWN Network.

Strayed’s fourth book, Brave Enough, was published in the United States by Knopf on October 27, 2015, and in the United Kingdom a week later by Atlantic Books. It debuted in the advice and self-help category on the New York Times Best Seller list at number 10.

Strayed’s book Tiny Beautiful Things was adapted for the stage by Nia Vardalos, who also starred in the role of Sugar/Cheryl. The play was directed by Thomas Kail and debuted at The Public Theater in New York City in 2016 and 2017. It is now being staged in several theaters around the nation.

Strayed is also a public speaker and often gives lectures about her life and books. She travels internationally to meet at writers retreats and lead writing seminars. In 2017, she taught a writing workshop to students at BlinkNow Foundation’s Kopila Valley School in Surkhet, Nepal; the conversations she had with girls at the school led her to make a short film on the topic of chhaupadi, a form of menstrual taboo which prohibits Hindu women and girls from participating in normal family activities while menstruating.

In August 2019, Strayed was one of ten women for whom statues were constructed in New York as part of Statues for Equality, a project conceived to balance gender representation in public art.

Strayed has hosted two hit podcasts for the New York Times. In 2020, she hosted Sugar Calling and from 2014-2018 she co-hosted Dear Sugars with Steve Almond. The podcast was produced by The New York Times and WBUR, Boston’s National Public Radio affiliate.