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WATCH: Shondaland’s Jennifer Romolini Blends ‘Weirdness’ with Work

How can misfits become bosses? Chief Content Officer of, Jennifer Romolini, answers that question in her new book, “Weird in a World That’s Not: A Career Guide for Misfits, F*ckups, and Failures.” On Bold Business, Jennifer shared her advice about finding your path when you feel out of place. 

Jennifer “failed, and failed, and failed and failed” before she got her first job. It took the now-author twenty-three interviews before she broke into the media business. And with no connections or friends in the city, Jennifer felt “really awkward” even once she made it to New York. Nevertheless, she succeeded: prior to her work at, Jennifer was the editor-in-chief of HelloGiggles.

Calling confidence “sort of overrated,” Jennifer pointed to competence as a key to success. According to Jennifer, it is hard work and determination that can turn you from an outsider to an entrepreneur.

Watch our interview with Jennifer here or on our Facebook page

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