Arriving in New York, Chesnutt was hired immediately as a reporter for Dow, Jones, & Company. Later he wrote for the New York Mail and Express, where he had a column called “Wall Street Gossip and News.”  Having access to the world of business, Chesnutt found New York to be cold and competitive. Even more, he found the city an unsuitable environment to raise his family.  Not wanting to remain in New York, and with no intention of returning to Fayetteville, Chesnutt looked to Cleveland and, after living in New York for six months, he moved his family to the city of his birth, where he would reside for the rest of his life.

Once in Cleveland, Chesnutt found work as a stenographer in the accounting department of the Nickel Plate Railroad Company, owned by the Vanderbilt family. That spring he moved Susan and their three children from Fayetteville into the first of their Cleveland residences. Just as Anne Marie disliked moving from Cleveland to Fayetteville, Susan disliked the move from Fayetteville to Cleveland. She missed the warm weather, her friends, and, with a husband now working in the day and writing at night and on weekends, the support she received from her family in raising the children. Threatening to return to Fayetteville, a compromise by hiring a young woman to help Susan manage the family. After being transferred to the legal department at Nickel Plate, Chesnutt began to study law under the guidance of Cleveland judge, Samuel Williamson. Chesnutt passed the bar with exceptionally high scores, and while Williamson was unwilling to offer him a position in his own firm, he helped Chesnutt did find work in another Cleveland law firm, not practicing law but receiving clients, with a salary so insufficient that he had to continue work as a stenographer to support his family.

Chesnutt was the proprietor of one of the most successful stenography businesses located in Cleveland in the early 20th-century.  According to his daughter, Helen, Chesnutt would take down speeches from campaigns and conventions in Cleveland and have them transcribed and reproduced through his office. Soon after passing the bar, his stenography business had grown to the point that he moved to larger offices in the Williamson Building, where lawyers from all over the country would keep headquarters while in Cleveland.  At one point, Chesnutt advertised for a partner but, having no satisfactory response, hired his sister Lillian, who had moved from Fayetteville.

Chesnutt’s work experience as a teacher, reporter, and bookkeeper at a railroad company, as well as a lawyer enabled his stenographic work to include a range of services adapted to every description. His various jobs kept him in contact with people, while his work experience provided a broad expose to professionals in the business world of the era. Like Charles Dickens, Chesnutt was also a court reporter and each acknowledged their work in this field as an important training ground for their literary careers. In Chesnutt’s case, the exposure acquainted him with vernacular of day-to-day life, the natural rhythms of speech as spoken by both the educated and the ill-educated, and a better understanding of the ways in which different populations conveyed meaning to one another.

Chesnutt continued to work in the day and write at night and on weekends. In 1886, he published a story in the Chicago Ledger. This was followed by seven stories in McClure’s Magazine, a new muckraking magazine that helped to launch Robert Louis Stevenson, Rudyard Kipling, and Jack London. Although McClure’s only paid an average of $15 per story, he gained attention as an emerging American writer.  In the next two years, Chesnutt had published nineteen stories in various publications and in 1888—unbeknownst to the publishers—he became the first African American writer to be published in the Atlantic Monthly. In 1889, Charles began a correspondence with George Washington Cable, a writer whom Chesnutt admired and who would influence Chesnutt’s writing over the next few years. Cable encouraged Chesnutt to turn from writing fiction to writing essays addressing inequality in American racial policy. Both men were active in The Open Letter Club, an organization that consisted of some three hundred prominent African American (male) members. Participants circulated speeches and essays about the race question to recipients that included southern men, whom they attempted to persuade through rational discourse.  In 1890 Chesnutt was appointed to the Resolutions Committee of the Board of Negro Ministers, which submitted a resolution to the U.S. Senate and House of Representatives to end the brutalization of Black Americans in the south.

Chesnutt was gaining a growing reputation as a short story writer and approached Houghton Mifflin, publisher of the Atlantic Monthly, about publishing a collection of stories. The publishers were hesitant, advising instead that he continue to write more short fiction and publish in other magazines. In 1896 Chesnutt learned there was a new editor at Atlantic Monthly, who because of his liberal politics, had relocated to New York from North Carolina.  Chesnutt contacted the editor and the two began to correspond. As a result, Houghton Mifflin published The Conjure Woman, the first volume of Chesnutt’s short fiction in 1899. Chesnutt continued to publish and the stenography business continued to grow. It had been Chesnutt’s dream to retire from the stenography business and focus on his writing full time. For years he had saved thousands of dollars to survive the expenses of the inevitable dry period until there would be enough money to make a living from his writing. In 1899, with his two oldest children in college, a new book and a reputable publisher, he did. The Conjure Woman was followed by a second volume of stories, The Wife of His Youth, then a short biography of Frederick Douglass. Between 1900 and 1905, he published three novels—The House Behind the Cedars, The Marrow of Tradition, and The Colonel’s Dream. While his novels generally received good reviews in the North, they received terrible reviews in the South. As a result, he was unable to achieve the sales of Stevenson, Kipling, or London and returned to his stenography business in 1906.

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Citizen Chesnutt:  Cleveland Timeline

It was not the publishing fees but Chesnutt’s business acumen that enabled him to provide for his family at a level and in a lifestyle more typical of the emerging black middle class. Because the Cleveland City Directory listed an individual’s employment, as well as the home address, the following time line traces Chesnutt’s moves to progressively larger homes located in more affluent neighborhoods as his business grew.

1883

In late November Chesnutt leaves New York for Cleveland without his family. He finds a place to room and board while using his stenographic skills to work as a clerk in the accounting department at the Nickel Plate Railroad Company.

1884

Chesnutt’s listing in the City Directory reads “clk. bds. 224 Garden.”

His wife, Susan and their three children join Chesnutt in April. The family moves to a small house on Wilcutt Avenue.

1885

Chesnutt’s occupation remains “Stenographer” in the City Directory. He is transferred to the Legal Department at the Nickel Plate Railroad Company and he continues his stenography. In addition, he begins to study law under the tutelage of Judge Samuel Eladsit Williamson.  That same year, the family moves to 67 Ashland Avenue.

1886

Chesnutt family moves to 85 Florence. In 1886, the City Directory lists the same line of work, but with a new home address, moving from 67 Ashland Avenue to 85 Florence.

1887

Chesnutt passes his bar exams. City Directory adds an additional business address:  Chesnutt, Charles W. lawyer, room 8, 219 Superior.

1889

City Directory lists residence as 64 Brenton. Business address changes to 30 Blackstone Building. Chesnutt is now listed as stenographer and attorney with his own practice.

1891

Chesnutt residence remains the same. Occupation remains the same but Chesnutt has moved from the one-room office in the Blackstone Building to a three-room office [701, 702, and 703] in the Society for Savings Building , in a practice listed as Pomerene & Chesnutt 1891 City Directory.

1893

Directory lists vocation as Attorney and Stenographer but Chesnutt is no longer affiliated with Pomerene. He remains in the Society for Savings Building but moves back into a one-room office.  His business address is listed as 736 Society for Savings Building.

1903

City Directory still lists Chesnutt’s home address as 64 Brenton. His business address is now 1005 Williamson Building, and a third designation added to occupation: Chesnutt, Charles W., Lawyer, Stenographer and Notary.

1904

Chesnutt’s trade and business address remain the same. City Directory lists home address as 1668 Lamont.  Chesnutt will remain in this fifth home for twenty-eight years until his death. The residence is described as: “a beautiful house with a wide porch and forty windows and polished hardwood floors in the spacious rooms”, with an entrance hall “large enough to serve as a dance floor and to accommodate an orchestra at Christmas parties.” There were fourteen rooms, and one of them was Charles’ library.

In 1905, Cleveland renamed and renumbered the streets throughout the city. According to the “Old and New Street Numbers Book“(Ref. F499.C675 042 190x), Chesnutt’s pre-1906 addresses convert to the following:

• 224 Garden (ca. 1883) became Garden Avenue. However, the 1906 map has “Central” in the same place where “Garden” was on the 1884 map.
• Wilcutt (ca 1884) looks like a continuation of E. 63rd on the 1906 map.
• 67 Ashland (ca 1885) became E. 65
• 1668 Lamont (ca. 1904) became 9719 Lamont Avenue

After 1905, Chesnutt’s business addresses converted to the following:

• 219 Superior became the area of the former U.S. Court House and now the twin of the Cleveland Public Library Main Library Building.
• Blackstone Building Society for Savings Bldg. became 127 Public Square, current site of the BP Building
• Williamson Building became 215 Euclid Avenue before being razed.

Unfortunately, none of these homes exist today: the 2485 E. 63 address is now part the site of a new public housing area; 2212 E. 73 is now a garage. In 1936, the family moved from 9719 Lamont, which was demolished and replaced by the  Charles Orr School.