Content Warning: This section of the guide discusses racism, alcohol use disorder, mental health conditions, and anti-LGBTQ+ biases in connection with the HIV/AIDS epidemic of the 1980s.

“This was the one I chose: my first serious job in New York City. A job which in some ways saved my life, and in other ways ruined it. What a smart girl.”

Rooney closes the first chapter with these lines about Lillian’s decision to take a job working at RH Macy’s. They center her work in advertising as the driving force behind her life for both good and bad, employing irony to play on the notion that being a “smart girl” was not what she had expected.

“Women in my day spent $150 million on cosmetics annually. I helped get them to do it. Tonight on the street, under orange lights, women will walk by, their arms through the elbows of their men in overcoats, their eyes lined in blue. The blue pencil I used in my day was to mark up copy, ad copy.”

Lillian contextualizes the power of advertising and her role in it, which she characterizes with the ironically positive “helped.” Her observations of the makeup the women wear emphasizes the passage of time and the changes that have occurred since she was young. The notice she takes of bright and contrasting colors also represents Lillian’s strong attention to detail.

“The use of the passive voice to disguise one’s role in the making of a decision is imprecise and obfuscatory. You’re a better adman than that.”

Lillian scolds her boss Chester for using the passive “it’s been decided” to explain why Macy’s cannot give her a raise. Her use of the term “adman” is intentional, as she is daring him to state outright what he doesn’t want to say: A woman simply isn’t allowed to make as much as a man.