In the 1930s, Winters had been a friend of David Lamson who had worked at Stanford University Press. Winters defended his friend when Lamson was accused and convicted of killing his wife; after serving time on death row, Lamson's case was re-tried and he was freed after two more trials and hung juries. Elman became familiar with the events, and the crime became the springboard for his novel, An Education In Blood. Winters was portrayed in the novel through the character of Jim Hill.

At Syracuse University (B. A., 1955), Elman's teachers, Daniel Curley and Donald Dike, encouraged his writing. At Syracuse, Elman met Emily Schorr, who became a Painter. They married in 1955, and in 1964 their daughter Margaret was born. The marriage ended in divorce. In 1979, Elman married Alice (Neufeld) Goode, a Teacher, who was his wife until his death. Their daughter Lila was born in 1981.

Elman studied English and creative writing at Stanford University (M.A. 1957) where he came under the influence of poet and critic Yvor Winters who taught there.

Elman returned to New York and worked for the Pacifica Foundation, WBAI, as a public affairs Director from 1961-64. He helped Bob Fass, a boyhood friend, get work there. At WBAI, Elman produced radio documentaries, such as a sound montage "The Last Days of Hart Crane", which featured tape-recorded interviews of people who had been close to the poet during his lifetime. The poet Robert Lowell, came to the studio to Listen to the montage, and later Lowell contributed to a second montage on Ford Madox Ford's American years.

Between 1963 and 1966 much of Elman's income was derived from writing freelance pieces for magazines, including Cavalier, Commonweal, The Nation, and The New Republic. He also reviewed books for The New York Times.

In 1965, Elman worked as a research associate for the School of Social Work Research Center at Columbia University. His work of non-fiction, The Poorhouse State: The American Way of Life On Public Assistance evolved from those experiences where he spent two years interviewing people on relief in New York's Lower East Side.

At various times over the course of his career, he taught creative writing: at Bennington College (1967–68), Bennington College Summer Writing Workshop (1974-), Columbia University (1968-1976), Sarah Lawrence (1970), The University of Pennsylvania (1981–83), University of Arizona (Fall 1985)Notre Dame, and Stony Brook University.

In 1968, he signed the "Writers and Editors War Tax Protest" pledge, vowing to refuse tax payments in protest against the Vietnam War.

His dark and hilarious book, Little Lives, written in 1978, was turned into a musical in 2004 with Words and Music by Rhett DeVelay. The songs were recorded in 2012.

Throughout the 1980s, Nicaragua colored Elman's imaginative life. His book of poems, In Chontales, his comic novel, The Menu Cypher, and his collection of stories, Disco Frito, are all set in Nicaragua.

Contemporary Authors Autobiography Series, Volume 3, ed. Adele Sarkissisan, Gale Research Company, Detroit, Michigan, 1986.

His book of poems, Cathedral-Tree-Train (1992) is a brooding, unsentimental but loving elegy for a friend, abstract-expressionist Painter Keith Sanzenbach.