Considered pop punk and power pop, "My Own Worst Enemy" is, according to Lit guitarist Jeremy Popoff, "the result of waking up and realizing you screwed up the night before". Vocalist A. Jay Popoff said that the song "was the combination of many, many incidents"; he had gotten in trouble with the law for public nudity in the late 1990s, and sang "My Own Worst Enemy" nude in the studio. The singer described a New Year's when the band got drunk in Laughlin, Nevada; he stole a janitor's cart, and he "and five friends jumped onto the flatbed, rode down the sidewalk, and got chased by the cops".