She was an illustrator for 25 years, with work featured in several publications including The Atlantic Monthly, Rollingstone, The New Yorker, The Washington Post, The Chicago Tribune, The New York Times, GQ and New York Magazine. Osborn began her painting career in 2014, showing in exhibitions at John Davis Gallery (2015), Geoffrey Young Gallery (2015), Gallery Molly Krom (2015) and at the Art on Paper Fair (2016).