Early career Strout moved to
New York City, where she waitressed and began developing early novels and stories to little success. She continued to write stories that were published in literary magazines, as well as in
Redbook and
Seventeen. She enrolled in Law School at
Syracuse University, and practiced law for six months before a funding cut ended her job as a Syracuse legal-services advocate. Strout worked for six or seven years to complete her book
Amy and Isabelle, which when published was shortlisted for the 2000
Orange Prize and nominated for the 2000
PEN/Faulkner Award for Fiction.
The New Yorker welcomed the novel with a positive review: "with superlative skill, Strout challenges us to examine what makes a good story—and what makes a good life." Strout's third book,
Olive Kitteridge, was published two years later in 2008. The book featured a collection of connected short stories about a woman and her immediate family and friends on the coast of Maine. Emily Nussbaum of
The New Yorker called the short stories "taciturn, elegant." In 2009, it was announced that the novel won the year's
Pulitzer Prize for Fiction. NPR noted the novel by saying: "This is an ambitious novel that wants to train its gaze on the flotsam and jetsam of thought, as well as on big-issue topics like the politics of immigration and the possibility of second chances." The book became her second
New York Times bestseller.
The Washington Post reviewed it with the following observation: "[T]he broad social and political range of The Burgess Boys shows just how impressively this extraordinary writer continues to develop." a story about Lucy Barton, a recovering patient from an operation who reconnects with her estranged mother.
The New York Times reviewed it with the following observation: "there is not a scintilla of sentimentality in this exquisite novel. Instead, in its careful words and vibrating silences,
My Name Is Lucy Barton offers us a rare wealth of emotion, from darkest suffering to—‘I was so happy. Oh, I was happy’—simple joy." The novel topped
The New York Times bestseller list. It was also longlisted for the
Man Booker Prize. Strout broke from her usual multi-year break in between novels to publish
Anything Is Possible (2017), her sixth novel.
Anything Is Possible was called a "literary mean joke"
Anything Is Possible won
The Story Prize for books published in 2017.'''' A sequel to
Olive Kitteridge, titled
Olive, Again, was published in October 2019.
Olive, Again was selected for Oprah's Book Club. In October 2021,
Oh William! was published. The novel revisits the world of Lucy Barton, and according to Strout, is primarily about "how hard it is ever to know anyone, including ourselves". It was named to the shortlist of the
2022 Booker Prize. A year later Strout published a pandemic novel,
Lucy by the Sea. It portrays Lucy and her ex-husband William quarantining in Maine. The New York Times Book review praised the "intimacy and candor" of Lucy's voice, noting that her halting rhythms resonate. In 2024, Strout returned to her characters Lucy Barton, Olive Kitteridge, Bob Burgess, and Isabelle Goodrow, now all living in Crosby, Maine, in
Tell Me Everything. Oprah selected the novel for her book club, and it was shortlisted for the 2025
Books Are My Bag Readers' Awards.
The Washington Post described it as "canny and radiant" and
The New York Times Book Review praised its "abundance of searing and plain-spoken insights." Other reviews were less favorable. Both
The New Republic and the
TLS found the novel suffered from sentimentality, with the latter describing it as a "jostling, jarring mess." ==Personal life==