Bossypants is a humorous memoir published in 2011 by actor and writer Tina Fey. Fey describes growing up as an awkward, smart-mouthed girl and traces the process by which she enters show business, from working at a theater summer camp, to taking night improv classes, to writing for Saturday Night Live, and finally to creating her own television sitcom, 30 Rock. Fey writes of the discrimination and double standards to which women in show business are subjected and suggests that they are a product of impossible, sometimes contradictory ideals placed on women by society at large. In order to rise in show business, she argues, women must overcome the urge to surrender to convention and to please an implacable public.

Fey’s mother is forty years old when Fey is born, and Fey learns at a young at that her parents are older. When she’s in kindergarten, her face is slashed by a stranger in an alley behind her house. She carries the scar to this day, and she believes she can tell a lot about people by the way they react to it. As she enters her teens, she begins to realize that women are judged for their bodies and that no body, no matter how conventionally beautiful, seems capable of satisfying the ideal.

The summer after 11th grade, Fey and her boyfriend work at Summer Showtime, a theater group that becomes a safe haven for gay teens. Her boyfriend breaks up with her, and Fey soothes her grief by hanging out with her theater friends. Fey is grateful to the founder of the camp for providing a space in which her gay friends feel included; she also learns valuable lessons about friendship. During this time, she sabotages the girl her boyfriend had left her for, something she now regrets.

Fey continues on to University of Virginia, where she has little luck in love. Unschooled in romance, she blithely attaches herself to boys who prefer blond, more conventional-looking girls, misreading signals and failing to recognize the platonic nature of their relationships.

After college, Fey moves to Chicago, where after a frustrating job search she begins working at the desk at the YMCA. There, she deals daily with an eclectic mix of coworkers, residents, and fixtures of the neighborhood. Working long hours and feeling disillusioned by a power hierarchy that props up incompetent men, Fey takes improv classes at night. Tired of having to cater to the ceaseless needs and demands of the residents, she is promoted to an office job, which she leaves in less than a year to begin working at The Second City theater company, “the most fun job” (74) of her life.

Fey works in the touring company of The Second City, traveling all over the country performing sketches. Fey loves the work she does, and the knowledge she gains at The Second City helps mold her career. However, she is vexed by the sexism of the producers, who cast more men than women because they fear the women are incapable of producing as much material and because they don’t believe audiences want to see sketches with more women.

In 1997, Fey is hired for a writing position at Saturday Night Live. Over the course of nine years she develops a close bond with Lorne Michaels, whose guidance will ultimately help her when she leads her own show, 30 Rock. In 2000, Fey joins Jimmy Fallon on Saturday Night Live’s "Weekend Update" and begins starring in a few other sketches. During this time, Fey takes steps not only in her career but also in her personal life: she and her husband marry in 2001 and suffer through a nightmarish honeymoon cruise.

As she continues in show business, Fey is indoctrinated into the world of photo shoots; she also discovers what it’s like to be the subject of harsh, often misogynistic internet comments. After eight years at Saturday Night Live, she’s encouraged by Lorne Michaels to develop an idea for her own show. After a long and stressful process, NBC picks up her sitcom 30 Rock, about a liberal head writer at a comedy show and her conservative boss, played by Alec Baldwin. Although the viewership is relatively small, the show is a critical success. Fey attributes part of what makes the show great to the humanness of its characters.

Alice, Fey’s daughter, is born in 2005. Fey is still working on 30 Rock in 2008 when Sarah Palin becomes John McCain’s running mate in the presidential race, and in response to massive public request, Fey returns to Saturday Night Live to play Sarah Palin, often opposite her friend Amy Poehler as Hillary Clinton or Katie Couric. She juggles her Saturday Night Live appearances with her work on 30 Rock. While she is delighted to return to Saturday Night Live in this capacity, she is the subject of criticism from conservatives and also from male media pundits who criticize her for being impolite.

The final chapters of Fey’s book are dedicated to musings on what it means to be a woman, specifically a working mother, and on the question of whether women truly can have it all. She writes about the condescension and judgment imposed on working mothers and on women who choose not to breastfeed. This judgment leads to feelings of failure and disappointment in women, who often feel insufficient no matter what their choices in life, thus demonstrating the futility of attempting to force oneself into conventions. By the end of the chapter, she has not decided whether she wants to have another baby, but she has come to understand that “everything will be fine” (250) regardless, encapsulating in the final paragraph her belief that improvisation is not only the root of her career but also her “worldview” (75).