From 1996 to 1999 Sheidlower worked for Random House as a senior editor, where he initiated their "Word of the Day" internet page, answering questions about lexicography.

In 1999, the Oxford English Dictionary hired him to manage their newly opened North American Office, based in Old Saybrook, Connecticut.

[11] In 2021, Sheidlower launched the Historical Dictionary of Science Fiction website, an expansion of the earlier Citations project.

[12] Sheidlower is an expert amateur cook and collects both cookbooks and bar paraphernalia; Food & Wine Magazine has written about his "famous Manhattan dinner parties".

Sheidlower has written against the censorship of obscenities in news coverage and court cases, arguing that a reliance on euphemisms can impede accurate reporting, deprive readers of integral information, and obscure the realities of racism, sexism, and homophobia.