In 1996, Oxford dropped out of Mount Royal University after one semester. She started blogging as a means of daily productivity and self-publishing. She later worked as a waitress and at a shoe store.
In 2001, Oxford became a full-time stay-at-home mother and began focusing on her online writing and scriptwriting. She started an anonymous blog in 2002, joined Twitter in 2009, and gained a large following, eventually attracting the attention of celebrities including Diablo Cody and Roger Ebert and being contacted by a number of agents. She sold a television script to CBS, to be executive produced by Jessica Alba, based on her life as a mother in Calgary. She then wrote another pilot that was bought by NBC. Neither script has been produced. Oxford moved to Los Angeles in 2012.
In 2013 Oxford published a semi-autobiographical book, Everything Is Perfect When You're a Liar, which became a New York Times bestseller.
In 2014 Oxford appeared on the reality show Candidly Nicole, starring Lionel Richie's daughter Nicole Richie.
Oxford and her husband James were together for 18 years until splitting up in fall 2016. They have three children: Salinger (Sal, born 2001), Henry (born 2003), and Beatrix (Bea, born 2008).
It was announced in March 2017 that Oxford was developing a '90s teen drama series for Hulu, with her The Disaster Artist collaborators James Franco, Seth Rogen, and Evan Goldberg producing.
