Penny comes to directing from 20 years experience as a playwright, screenwriter, and advertising copywriter. She is the author of the stage play now then again, which premiered in Chicago, won a Joseph Jefferson Citation for "Best New Work" and was published by Broadway Play Publishing. Her screenplay adaptation, titled Love is Brilliant, won the Sloan Award at the 2005 Tribeca Film Festival. Penny is the author of numerous other screenplays. Her short film script, One in a Million, starring Carrie Coon, was produced with Fulton Market Films. She has received stage productions, workshops, and commissions from theaters such as Portland Center Stage, Milwaukee Repertory, Theater Wit, Shakespeare's Motley Crew, Bailiwick Repertory, Stage Left Theatre, The Old Globe, and Lookingglass Theatre. Penny is a former Adjunct Professor of Playwriting at Northwestern University. She has written articles on screenwriting for MovieMaker Magazine and lectured internationally on dialogue writing technique. Her book Talk the Talk: A Dialogue Workshop for Scriptwriters was published by MWP Books.
As an advertising copywriter, Penny has written national television, radio, and print ads for brands such as: Huffy Bicycles, Red Lobster Restaurants, Clearasil, Metamucil, Hardee’s, Kemper Financial Services, Hoover, Ameritech, and The League of Chicago Theaters. In addition to her produced advertisements, she has participated in market research and identity development for brands such as Chex Cereal, Kay Jewelers, Jared the Galleria of Jewelry, Coast Soap, Old Spice, Dick’s Sporting Goods, Head and Shoulders Shampoo, Purina, The Center for Ethics and The American Bar Association.
Penny has developed corporate communication pieces for clients such as The Department of Internal Medicine at Rush University Hospitals, Svenska Cellulosa Aktiebolaget (SCA Paper), Trane Air-Conditioning Systems, Mimic Technologies, and The Lab School of Chicago. In 2004, her television campaign for the League of Chicago Theaters won a Summit Creative Award.