After failing his school exams, Gibbs began a series of dead-end jobs including working as a timekeeper, a chauffeur, a draftsman, and four years on the freight crew of the Long Island Railroad, which his uncle was affiliated with. Realizing he was unhappy and unfulfilled in his work, his cousin, Alice Duer Miller, set him up working as an editor for their cousin through marriage, Lloyd Carpenter Griscom. Griscom made Gibbs the associate editor of the "East Norwich Enterprise" and, eventually, reporter and editor for the "North Hempstead Record", both Long Island newspapers. Gibbs succeeded and eventually went to "The New Yorker" in 1927 as a copy reader. Ten years later, when E. B. White temporarily left the magazine, he took over the "Talk of the Town" section.