Business, marriage and family

During his time in Springfield, Anderson stayed (and worked as a "chore boy") in a boardinghouse called The Oaks among a group of businessmen, educators, and other creatives types many of whom became friendly with the young Anderson.^[39] In particular, a high school teacher named Trillena White and a businessman Harry Simmons played a role in the author's life. The former who was ten years Anderson's senior would walk - raising eyebrows among the other boarders - with the young man in the evenings. More importantly, according to Anderson, she "...first introduced me to fine literature"^[40] and would later serve as inspiration for a number of his characters including the teacher Kate Swift in Winesburg, Ohio. ^[41][42] The latter, who worked as the advertising manager for Mast, Crowell, and Kirkpatrick (later Crowell-Collier Publishing Company, publishers of the Woman's Home Companion) and occasionally took meals at The Oaks, was so impressed by Anderson's commencement speech that he offered him a job on the spot as an advertising solicitor at his company's Chicago office.^[41] Thus, in the summer of 1900, Anderson returned to Chicago where the bulk of his siblings were now living, intent on achieving success in his new white-collar occupation.^[43]

Though he performed well, problems with his boss and a dislike for the office routine (including style of correspondence, which caused the ultimate rift) caused Anderson to leave Crowell in mid-1901 for a position set up for him by Marco Marrow, another friend from The Oaks, at the Frank B. White Advertising Company (later the Long-Critchfield Agency).^[44] There the author stayed until 1906, selling ads and writing advertising copy for manufacturers of farming implements and articles for the trade journal, Agricultural Advertising. ^[45] In this latter magazine came Anderson's first professional publication, a February 1902 piece called "The Farmer Wears Clothes".^[46] What followed were approximately 29 articles and essays for his company's magazine, and two for a small literary magazine published by the Bobbs-Merrill Company called The Reader. ^[47] According to scholar Welford Dunaway Taylor, the two monthly columns ("Rot and Reason" and "Business Types") Anderson wrote for Agricultural Advertising exemplified the "character writing" (or character sketches) that would later become a notable part of the author's approach in Winesburg, Ohio and other works.^[48]

Advertisement for the Anderson Manufacturing Co., a company owned by Sherwood Anderson from 1907-1913, almost a decade before he became a well-known author.

Part of Anderson's job in those early years of his career was making trips to solicit potential clients. On one of these trips around May 1903 he stopped in the home of a friend from Clyde, Jane "Jennie" Bemis, then living in Toledo, Ohio. It was there that he met Cornelia Pratt Lane (1877–1967), the daughter of wealthy Ohio businessman Robert Lane. The two were married a year later, on the 16th of May. They would go on to have three children — Robert Lane (1907–1951), John Sherwood (1908–1995), and Marion (aka Mimi, 1911–1996).^[50] After a short honeymoon, the couple moved into an apartment on the south side of Chicago.^[51] For two more years, Anderson worked for Long-Critchfield until an opportunity came along from one of the accounts he managed and so on Labor Day 1906, Sherwood Anderson left Chicago for Cleveland to become president of United Factories Company, a mail-order firm selling various items from surrounding firms.^[52]

While his new job, which amounted to the position of sales manager, could be stressful^[53] the happy home life Cornelia had fostered in Chicago continued in Cleveland; "his wife and he entertained frequently. They went to church on Sundays, with Anderson decked out in morning clothes and top hat. On occasional Sunday afternoons Cornelia taught him French. She also helped with his advertising work".^[54] Unfortunately, his home life could not sustain him when one of the manufacturers United Factories marketed produced a large batch of defective incubators. Soon, letters addressed to Anderson (who personally guaranteed all products sold) began to arrive from customers both desperate and angry. The strain from months of answering hundreds of these letters while continuing his demanding schedule at work and home led to a nervous breakdown in the summer of 1907 and eventually his departure from the company.^[55]

His failure in Cleveland did not delay him for long however, because in September 1907, the Andersons moved to Elyria, Ohio, a town of approximately ten thousand residents, where he rented a warehouse within sight of the railroad and began a mail-order business selling (at a markup of 500%) a preservative paint called "Roof-Fix".^[56] The first years in Elyria went very well for Anderson and family; two more children were added for a total of three in addition to a busy social life for their parents.^[57] So well, in fact, did the Anderson Manufacturing Co. do that Anderson was able to purchase and absorb several similar businesses and expand his firm's product-lines under the name Anderson Paint Company.^[58] Carrying on that momentum, in late 1911 Anderson secured the financial backing to merge his companies into the American Merchants Company, a profit-sharing/investment firm operating in part on a scheme he developed around that time called "Commercial Democracy".^[59][60]

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