This song finds Jennifer Nettles encouraging a struggling young woman who is trying to handle everything all by herself. Said her musical partner Kristian Bush: "I saw my mom as that person. I see pieces of it in my own daughter. Jennifer is certainly one of those women."

The song is one of The Incredible Machine's earliest penned tracks. "We were at a festival over a year ago and I was on the bus doing my makeup while Kristian was warming up," recalled Nettles in publicity materials. "I was wearing a checkered dress and he started playing this lick and singing, 'Little Miss checkered dress.' I popped my head out and sang, 'Little Miss one big mess!' The way that song was discovered was fun and really beautiful."