As a teenager in the 1990s, Woolfe discovered the online opera magazine Parterre Box by James Jorden, whose pages he "returned to again and again".
[2] Although he "had written a little bit for newspapers in college", he had not anticipated a career in journalism.
[3] In 2008, however, a friend at The New York Observer asked Woolfe to assist in coverage of the 2008 US Open tennis tournament.
[3] After additional writing for the paper, Woolfe was offered a regular column in 2009, devoted to opera.
[3] In 2011 Woolfe started working as a freelance music critic for The New York Times, reporting on opera festivals in the US and internationally.