In 1878, Chesnutt married Susan Perry and then started a family (four children in all) soon after. When he was in his twenties, he was a prominent principal with a wife and children, but he longed for a writing career. In 1879, he confided to his journal that he planned to move North to “get employment in some literary avocation, or something leading in that direction.” Two years later, he confided to his journal, “Every time I read a good novel, I want to write one. It is the dream of my life—to be an author!” In the early 1880s, Chesnutt tried to work as a journalist in Washington, D.C., returned to North Carolina, then tried working in New York City, and finally moved his wife and children to Cleveland, Ohio, where he worked as a legal clerk–stenographer. He soon set up his own profitable legal stenography business while studying to pass the bar. In 1887, he was admitted to the Ohio bar and added a law practice to his stenography firm. In addition, in his spare time in the evenings, he wrote short stories.

He soon received some assurance that his efforts were worthwhile, when his story “The Goophered Grapevine” became the first short story by a black writer to be published in the highly revered Atlantic Monthly. Like the traditional plantation stories by white authors, Chesnutt’s story centered around an ex-slave African-American storyteller, Uncle Julius McAdoo, who spun delightful antebellum recollections of Southern life. Unlike the white authors’ narrators, however, Uncle McAdoo described a much less idyllic picture of the antebellum South and offered a much more realistic portrait of African-American folk culture. According to McAdoo, the slaves used trickery and deception to subvert their masters’ dominance and brutality; they weren’t cheerfully looking forward to complying with the kind requests of their masters.

The next year (1888), the Atlantic Monthly published Chesnutt’s “Po’ Sandy.” Chesnutt continued to split his time between his literary pursuits and his legal career until the fall of 1899, when he closed his prosperous business to pursue writing as a full-time career. He felt certain that his book sales and his speaking engagements would suffice to support himself and his family, so he dedicated a few years to writing three novels. By the time he started writing his third novel, however, he realized that his particular books would not sell widely enough to sustain him and his family, so in 1902, he reopened his court-reporting business and his law practice.

Over his literary career, Chesnutt published more than 50 tales, short stories, and essays, and he wrote 4 novels and a biography. In 1899, he published his biography, Frederick Douglass, and 2 short-story collections. His first short-story collection, The Conjure Woman, illuminates the relationships between white employers (or slave owners) and black servants (or slaves), as seen through the eyes of a black man who is a servant to a white man who has moved from the North to the South. It sold so well that his publisher (Houghton Mifflin) rushed the publication (the same year) of his second short-story collection, The Wife of His Youth and Other Stories of the Color Line. This second collection studies color prejudice among blacks, as well as between blacks and whites, by examining the racial identity of mixed-race Americans.

Chesnutt’s first novel, The House behind the Cedars (1900; originally called “Rena Walden”), dealt with interracial marriage and with a young girl’s attempt to pass for white. Although it was generally well received, it didn’t sell widely or well (although it did go to four printings rather quickly). His second novel, The Marrow of Tradition (1901), was based on a true incident and addressed the pervasive white supremacist activities and violence of the post-Reconstruction South. Despite the book’s nationwide reviews touting it as a timely but disturbing study, the book did not sell well. Chesnutt’s next literary venture was a romance novel, for which he couldn’t find a publisher. His 1905 novel The Colonel’s Dream (published by Doubleday) explored the problems of freed slaves struggling against prejudice and exploitation in a Southern town. When this novel sold poorly, too, Chesnutt lost faith in his ability to become rich and famous through his literary career, and he stopped writing novel-length fiction.

With two of his daughters in college and two younger children still at home, Chesnutt needed to realistically plan for the many demands on his financial resources. Perhaps he had also been unrealistic in his expectation that writing was likely to provide fame and fortune. For instance, he noted in his journal, “I want fame; I want money; . . . literature pays—the successful.” Chesnutt also loved writing for its own sake, however: “There is a fascination about this calling that draws a scribbler irresistibly toward his room. He knows the chance of success is hardly one out of a hundred; but he is foolish enough to believe, or sanguine enough to hope, that he will be the successful one.”

Although his career in writing proved less successful than he had expected, he was pleasantly surprised by the financial rewards of his legal career. Thus, contrary to his expectations, his other pursuits proved more financially rewarding than did writing. He still continued to write and speak on social and political issues of interest to him, but he wrote only a handful of short stories and an unpublished novel (“The Quarry”) during the final 25 years of his life.

Although his financial rewards for writing may have fallen short of his expectations, his literary achievements were nonetheless important. For one thing, he is now widely recognized as one of the first American writers to realistically portray African-American experience. He is also generally considered the first major African-American novelist, though his short stories may have been a more valuable contribution to U.S. literature than his novels. In any case, Chesnutt was the first African-American writer to have mainstream white-controlled presses publish his candid writings about the racially oppressed lives of African Americans in the South.

Chesnutt used his fiction, rooted in African-American experience, to address social injustice, racial discrimination, and a wide array of other issues and problems in American life, particularly those among African Americans in the post–Civil War era. As he said, “The object of my writings would be not so much the elevation of the colored people as the elevation of the whites—for I consider [the unjust treatment of colored people] a barrier to the moral progress of the American people.”

In 1928, the National Association for the Advancement of Colored People awarded Chesnutt its venerable Spingarn Medal for his “pioneer work as a literary artist depicting the life and struggles of Americans of Negro descent, and for his long and useful career as scholar, worker, and freeman of one of America’s greatest cities.” Despite poor health, he managed to publish his literary autobiographical essay, “Post-Bellum—Pre-Harlem” in 1931.