Sicha began his writing career as an editor for Gawker, The New York Observer, and Radar Online.[2] He launched The Awl in April 2009, with Alex Balk and David Cho, out of his East Village apartment,[3] after Radar magazine folded.[4] The website, described as a "irreverent, all-purpose, media/culture/politics/think-piece/bear-video clusterfuck" by GQ,[5] was based in downtown Brooklyn.[6] Sicha published his first book, Very Recent History: An Entirely Factual Account of a Year (c. AD 2009) in a Large City in 2013.[2]
Sicha became the editor of The New York Times Style section in September 2017.[1] On June 7, 2021, New York announced that Sicha had left The New York Times, and would join the magazine as an editor-at-large.[8]