At fourteen years old, a spot opened up in the exclusive Windsor Academy, and Kennedy Rhodes was offered admission. She turns it down to attend the same public school as her new boyfriend Austin, who she has been waiting to date for years. 3 years later, Kennedy Rhodes is editor in chief of her school newspaper which she started with her best friend, Laney. Her future looks bright and she dreams of studying journalism at Columbia University. However when her alumni interview is a disaster and she catches Austin cheating on her with Laney, she wonders what would happen if she accepted the offer to Windsor all those years ago, and she is transported to an alternate universe where she did just that.

Kennedy wakes up in Windsor Academy to find that her best friend in this world is Sequoia, a girl that she idolized and idealized on Instagram. Sequoia, who on Instagram looks perfect and happy, is actually deeply insecure and emotionally unstable as a result of the school's culture and her family life. She has a twin sister who is a musical genius who her parents often compare her to. Her sister often wins first place in piano competitions at her music school, while Sequoia is ranked number eight in GPA at her school. Sequoia reveals that at least if she were ranked first, academic could be her "thing" to shine at and make her parents proud, but since she isn't she feels like she can never measure up to her perfect sister.

Kennedy, who for a supposedly smart person takes a long time to realize her father no longer lives with them, calls him and finds out that he took a job at an advertising agency which, in her original life, he claimed he would never accept job offers from as he didn't want to become a "corporate sellout." From the phone call to her father Kennedy notices that he is similarly stressed out and miserable. Kennedy wistfully recalls how, in her other life, her dad was a happy stay-at-home parent who worked in a photography studio in the family basement and was poised to showcase his work at a gallery for the first time. She realizes that, in order to pay for her fancy private school's tuition, her dad had to give up his dream for hers.

In her new do-over alumni interview, Kennedy discovers that this version of her applied to be an economics major at Columbia, and has described herself as passionate about things such as "robotics", "financial consulting", and "donating money to the school", and various others, none of which are real passions as there is no real excitement shown for any of them. These interests are clearly what the faculty at the school drilled into their students to make them all alike.

She also learns that this version of her is so depressed at how lifeless she now is and how much she's ruined her family's life that she went to drastic measures as a way to "repay" them. This book is a bubbly yet heart wrenching read about how, even though you might make mistakes in life, sometimes you are better off with the choices you made, and the grass isn't always greener on the other side.