Graham unpacks the period of her life when her priorities began to shift. For years, she had been focusing primarily upon building up her acting career, but she suddenly realized that all of her friends were hitting different milestones, such as getting married and starting families. She thought, “These married-with-children people were still my friends, but they’d become part of a community I wasn’t in, a club I didn’t belong to” (90). Around this time, she began to consider the idea of finding a romantic partner.

Graham then discusses the difficulty she faced during this time. Many people her age had already built long-term relationships, and because she often found herself attending awards shows with her father, cousin, or friend, talk show hosts began asking awkward questions about her love life. One fan even went so far as to urge Graham’s father to tell her not to abandon the idea of finding love. Graham found herself wishing for a real-life advice booth just like the one that Lucy uses in the Peanuts cartoons.

Eventually, Graham began a romantic relationship with Peter Krause, an actor with whom she once presented an award and with whom she co-starred on Parenthood five years later. When Graham traveled with Krause to northern California to visit his family, she “stopped short in the middle of the Sonoma County airport” because the lobby sported “a life-sized Lucy advice booth” (99). She marveled at the irony of seeing the very advice booth that she had wished for when her love life seemed bleak. Even though this booth was primarily for tourist maps and brochures, Graham saw it as a sign confirming that she had found love in exactly the right place when she became involved with Peter Krause.

In this chapter, Graham describes some of the day jobs that she had before she found full-time work as an actor. In her younger days, she acted in commercials and grew to appreciate the productive feeling that she gained from “the routine of auditioning” (104), even when she didn’t get the job. She was never too proud to take commercial work, even though some of her peers felt that such roles were not sufficiently artistic.

Graham recalls attending a Labor Day party with Peter at the home of one of his former professors. To celebrate the holiday, he “asked everyone to write down all the jobs they’d ever done to make money” (105). The people at the party had held a variety of jobs over the years, and Peter had even been “a puppeteer with a mobile puppet stage” (106). Graham had worked as a bus driver for a summer camp and spent one summer as a receptionist at a hair salon.

After nearly three years of working on commercials and gaining a few small roles on soap operas, Graham was cast in a supporting role for a show at the George Street Playhouse in New Jersey. This was her first union gig since her work at the Barn Theatre. Graham explains that her myriad of jobs over the years paid the bills and made her passion for acting possible. She asserts that although it is “an accomplishment to do something well,” it is an “even a bigger one to do something well when you’d really rather not be doing it at all” (111).

Graham openly admits that she is not an expert on fashion. She recalls wearing oversized men’s shirts and corduroy pants; at one point, she even stapled her jeans to make the legs straighter because she didn’t want to do any sewing. However, there are many fashionable women in her family, and she writes that the first two decades of her life “were [her] dormant phase” (116). She was certain that she would finally be seen as fashionable when she was asked to be a judge on Project Runway, alongside another guest judge, Pat Field (the stylist for Sex and the City), and “regular judges Michael Kors and Nina Garcia, and […] supermodel Heidi Klum” (117). Graham states that although the experience seemed exciting and magical, it soon took a turn for the worse.

On the day of the show, the competition was a blur for Graham. When the time came for her to turn in her cards with her scores for the contestants, she quickly “wrote down as much as [she] could remember and assigned some scores randomly” (119). She wasn’t sure what to say when she had to give her critique, so she said something “benign. But the girl [she was critiquing] looked as if [she’d] punched her, and that’s when [she] realized […] that [she] didn’t like being a judge” (120). This incident marked Graham’s first experience with playing the role of a judge, and she felt especially unqualified. Graham concludes that she prefers to watch Project Runway at home rather than doing the judging.

In this chapter, Graham outlines the factors that led to her first writing venture: a novel titled Someday, Someday Maybe. In 2011, “for the first time in what felt like years, [she] realized [she] had something [she] almost never had: extra time on [her] hands” (126). As she reflected on the years of hard work and doubt that had filled her career, she pondered the universality of “dreaming big, growing up, and forging a career” (128). From there, she created the story of Franny Banks, a young girl who moves to New York City in the 1990s and gives herself a year, at the end of which she will move back home if she has not found success as an actress.

Graham found that she loved the creativity of writing the novel, and the pages flowed from her effortlessly. After she mentioned the story-in-progress to her agent, he read the pages she had written and sent them to “one of the best and best-known agents at ICM and in the galaxy, Esther Newberg” (130). Newberg felt the novel had potential, and after discussing it with Graham, sent it to three book editors “who would only take it on because they believed in [Graham] and the book” (132). Of those three, Graham chose Jennifer (Jen) E. Smith to become her editor for Someday, Someday, Maybe. Jen proved to be the perfect editor for Graham. She was straightforward and also encouraged her when she struggled to write. Most importantly, Jen became a trusted friend. The path ahead proved difficult, as Graham had entered another competitive field rife with unwanted opinions. One of the most common and frustrating comments that Graham has received about Someday, Someday, Maybe is the assumption that it must be autobiographical. Several reviewers and interviewers refused to believe that it was a work of fiction rather than a repackaged diary sold for a monetary gain.

Graham highlights the double standard for that women, unlike men, must navigate in the entertainment industry. She gives an example, saying that when Ron Howard “was first starting out as a director, no one ever asked who ‘helped him’ direct Tom Hanks in Splash” (138). Graham states that in an industry that holds sexist views against women, her best allies have been other women in positions of power. She says that Amy Sherman Palladino and Ellen DeGeneres gave Graham her biggest breaks in Hollywood. She directly urges her readers to “keep lifting each other up” (139), and she vows to do the same for them.