[2] Olsen was born to Russian Jewish immigrant parents Samuel and Ida Lerner in Wahoo, Nebraska; the family moved to Omaha while she was a young child.

[3] There she attended Lake School in the Near North Side through the eighth grade, living among the city's Jewish community.

[3] She was briefly jailed in 1934 while organizing a packing house workers' union (the charge was "making loud and unusual noise"), an experience she wrote about in The Nation, The New Republic,[6] and Partisan Review.

[7] She later moved to San Francisco, California, where in 1936 she met and lived with Jack Olsen, who was an organizer and a longshoreman.

[1] During the 1930s, Olsen attempted to introduce the challenges of her own life and contemporary social/political circumstances into a novel which she had begun writing when she was only nineteen.

Reportage was defined by Joseph North at the 1935 National Writers Conference held in New York City of as "three-dimensional reporting...both an analysis and an experience, culminating in a course of action.

[12] Olsen did not publish her first book until 1961, Tell Me a Riddle, a collection of four short stories, mostly linked by the characters who are members of one family.

"I Stand Here Ironing" is the first and shortest story in the collection, about a woman who is grieving about her daughter's life and questioning the circumstances that shaped her own mothering.

"O Yes" is the story of a white woman whose young daughter's friendship with a black girl is narrowed and ultimately ended by the pressures of junior high school.

", is told by an aging merchant marine sailor whose friendship with a San Francisco family (relatives of the main character in "Tell Me a Riddle") is becoming increasingly strained due to his alcoholism.

Reviewing Olsen's life in The New York Times Book Review, Margaret Atwood attributed Olsen's relatively small output to her full life as a wife and mother, a "grueling obstacle course" experienced by many women writers.