Cal meets his polar opposite: The Boss in Heals. Heather Monahan. Whereas Cal was told as a writer in Journalism School never to sell, Heather came up on the sales side being told not to think of herself as a creative talent. She rose up the corporate ladder to become Chief Revenue Officer of the Beasley Media Group with 500 people working for her and was named one of the most influential women in radio only to see her job eliminated in a power struggle. But she used that tumultuous experience to turn herself into the author of the book Confidence Creator, and she is now a speaker and consultant on the topic. “Confidence,” she says, “is a skill to be developed.” She shows Cal how to be confident in areas where he doesn’t feel comfortable – and you’ll get a lot of tips, too