She was previously a member of the art business faculty at the Sotheby’s Institute and taught courses in business as a design medium at the School of Visual Arts, the Rhode Island School of Design, and Williams College. From 2015 to 2016, Whitaker was the first entrepreneur-in-residence at the New Museum Incubator. She has also worked in finance, art museums, and start-ups. Whitaker’s most recent book, Art Thinking, has been featured in the Financial Times, Vanity Fair, the Boston Globe, and elsewhere.