Jessica worked as a stand-up comedian and comedic musician in New York City from the early 2000s, touring on the success of the aforementioned viral video from 2006 until more recently, when motherhood took center stage. She shifted her focus to writing satire, essays and articles for publications such as The New Yorker Shouts, McSweeney's Internet Tendency, The New York Times, Working Mother, Mother Magazine, The Atlantic, SELF Magazine, Huffington Post and Pitchfork. Her short, comedic parenting essay "Driving Under The Influence Of Child" was also featured in Gestalten's parenting book published in August 2020, and her writing was included in Lenka Clayton's, "Mothers' Days" journal.