Diary of a Wimpy Kid follows one student on his journey to navigate the waters of middle school and find his place in the hierarchy of his school. Greg makes it clear that he dreams of being rich and famous, and he believes that his pathway to success begins in middle school. Over the course of his school year, however, Greg tries and fails to attain popularity again and again. Kinney uses Greg’s failures to remind the reader that the journey to achieve popularity and acceptance can become all-consuming and cause a person to forget who they really are in the process.

Greg remembers how simple it was to be popular in elementary school. He complains that “[n]owadays, it’s a whole lot more complicated. Now it’s about the kind of clothes you wear or how rich you are or if you have a cute butt or whatever” (6). Middle school changes the dynamics of social groups as more students hit puberty and begin to change friend groups, and Greg feels like he has to “scramble” to gain popularity before it’s too late. He figures that he’s “somewhere around 52nd or 53rd most popular this year” (7) while Rowley is “probably hovering right around the 150 mark” (8).