She began her career in 1988 as a copy editor for San Diego Magazine, then wrote for the Financial Section of the city’s daily newspaper, the San Diego Tribune (now the Union/Tribune). In 1989 she moved to Atlanta and wrote feature and investigative pieces for Creative Loafing, then the fourth largest alternative publication in the nation. Her celebrated humor column, “Mood Swing,” first appeared in Poets, Artists & Madmen in 1996 and moved to Creative Loafing in 2000, where she was voted the city’s “best columnist” six out of the next eight years. Atlanta magazine picked up the column in 2007, where it appeared until October, 2014.
Gillespie founded the Shocking Real Life Writing Academy in 2007. Since then it has grown into the largest independent writing school in the Southeast.
Gillespie’s work has been optioned by Sony Pictures and Paramount, and she has collaborated with Hollywood hard hitters like Mitch Hurwitz, the creator of Arrested Development, Eric and Kim Tannenbaum, producers of Two and a Half Men, and Amy Palladino, creator of Gilmore Girls. Hollis runs Shocking Real Life, the largest writing school in the Southeast, which offers workshops on book writing, screenwriting, blogging and social media. Kirkus Reviews lauded Gillespie’s “impeccable comic timing” for her first novel, titled Unaccompanied Minor (“A laugh-out-loud thriller about family court, money laundering and skyjacking”). For the same novel, Booklist heralded Gillespie as “a fantastic narrator: smart, funny, angry, and gifted in sarcasm.” Her fifth, titled We Will Be Crashing Shortly, was released in 2015.