“I’ve learned a lot over the past ten years about what it means to be the boss of people.” 

Fey explains why her book is called Bossypants: “Ever since I became an executive producer of 30 Rock, people have asked me, ‘Is it hard for you, being the boss?’ and ‘Is it uncomfortable for you to be the person in charge?’” (5). She ironically adds that people probably ask Donald Trump the same question—suggesting, of course, that no one would ask a man whether he found being in charge uncomfortable, that managing people is seen as a uniquely male quality. Throughout her book, Fey discusses the requirements of conventional womanhood and how women who defy these conventions are judged. Her title suggests that women who are “the boss” are considered “bossy” and that women must overcome prejudice in order to rise in their fields.

“Almost everyone first realized they were becoming a grown woman when some dude did something nasty to them.” 

At a workshop, women are asked to identity “the moment when they first ‘knew they were a woman’” (16). In choosing moments in which men objectified them foretells the many incidents of objectification Fey describes throughout Bossypants. Fey’s decision to include this example in a chapter about growing up suggests that learning of their sexual objectivity is a major facet of girls’ growth into womanhood. The incident’s appearance in such an early chapter further foreshadows that sexual objectivity will be a theme in Bossypants.