Taylor moved to New York shortly after his birth and grew up in the Manhattan neighborhoods of Greenwich Village and Yorkville. Taylor attended public schools in New York City and excelled at writing evidenced by winning a prize for an original story. From 1881-82, he attended the College of the City of New York (the former name of New York University’s undergraduate college). His original ambition was to become a lawyer, but after two years of studying law, he began to lose interest. He was attracted to music but felt as though he lacked sufficient talent to become a great artist. After he graduated from CCNY, Taylor pursued instead his passion for writing and chose the field of journalism. In 1883, he published his own magazine, "The Aerolite", which did not have much success. Harrison Grey Fiske, an established New York journalist, playwright, and theatrical manager, wrote a serial for the paper. In 1887, he moved to Montpelier, Vermont, and worked for "The Argus", "The Patriot", and later, "The Watchman". His column, the "Montpellier Mere Mention", was the prototype for his famous "A Line o' Type or Two" column at the "Chicago Tribune". Taylor was known for his unique offhand writing style and independent spirit that often compromised his job at those early papers. He later moved south to Barre to start his own paper. The "Barre Daily News" ran only for a few months, and frustrated from the lack of support from the citizens and local businessmen, he printed the final issue in red ink as a reprisal before leaving town.