Tracy Flick Can’t Win by Tom Perrotta is about an assistant high school principal who feels stuck and unacknowledged at her job and in life. Tracy works tirelessly at her job and feels that she should be further along at this stage in her life. When she hears that the current principal, Jack Weede, is retiring, Tracy’s sullen moods are lifted and energized by the news, as she expects to be promoted to his position. She feels that the promotion is long overdue because she has acted as a temporary principal when Jack was on medical leave. Tracy throws herself into her work hoping that she can convince the School Board and faculty that she is well qualified for the job. However, as Tracy tries to focus her attention on getting promoted, she feels herself being pulled in different directions away from her goal. Tracy’s 10 year old daughter wants to spend more time with her father than with her; Tracy’s “boyfriend” is needy and wants Tracy to make a decision about their relationship; and Tracy has a non-existent social life and is in desperate need of a true friend.
Tracy tries to juggle all of life’s demands flawlessly but that doesn’t seem to help because nothing goes her way. Her male colleagues are determined to undermine her goals and progress to further their own interests. One of the demands of her role involves a new initiative by the school board to honor past students with an award. As time progresses and Tracy and the board try to work through the different candidates, she notices that something feels off. She knows she has a proven track record but she feels that something is going on behind her back.
This is the second novel by the author featuring Tracy Flick as the protagonist. I was able to read the novel as a standalone. However, I feel like I didn’t really get to know Tracy as a character in this book. She just seemed like an ambitious person who had to settle in life after one too many obstacles were thrown at her. For example, it seems that her non-existent relationship with her daughter bugs her. Tracy constantly laments that she had a great relationship with her mother and that she doesn’t understand why she doesn’t connect with her own daughter. Tracy seems like she is just going through the emotions being with her daughter instead of making an actual effort to bond with her.
Perhaps it’s because the book is narrated by several different characters with only a few pages dedicated to each person at a time, I feel like the characters were never really fully fleshed out and each character only progressed the story a tiny bit. After a while, it was confusing to keep track of the different characters and what role they played in the story. I felt that 90% of the book was rather pointless and had no story progression and purpose. The last 10% of the book is when the story wraps up and the link between all the characters is revealed in a rather lackluster way. The book is a quick read with its short chapters but it's boring with no story or purpose page after page.
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