Illustration by Payton Cosell Turner

Jennifer Romolini is my former boss. Well, she was my boss’s boss, really, at Yahoo, over two years ago, and she was a strong but empathetic figure. Her media career before and after Yahoo has been impressive, but she moved to New York as a self-proclaimed “awkward 27-year-old misfit,” the skinny, long-limbed daughter of a working-class Philadelphia couple. Her new book, Weird in a World That’s Not, which is part memoir and part career guide, begins, “I am not supposed to be here. I spent the first 28 years of my life as a fuckup and a failure. I failed and I failed and I failed.” So how did she become my boss’s boss? How did she grow HelloGiggles’ traffic by 500 percent, as the website’s editor in chief? How did she get to the point where she wrote a book about professional success?

Listen below to find out. 

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