Fray singer Issac Slade wrote this song while staying in a cottage, located in Breckenridge in the mountains of Colorado. He had with him a coffee table book that contained a picture called "Strictly a Sharpshooter" by American painter and illustrator Normal Rockwell, which depicted a boxer about to succumb to his opponent. Speaking to interviewer Mike Ragogna, Slade explained: "I just sat down at a piano and stared at the painting. He is one of my favorite painters. It's a scene where the fighter and his opponent are going at it and there's a girl standing in the crowd shouting, 'No!' I just really like the idea of this desperate and hopeless fighter trying to get through life. I think he and his girlfriend both know he's going to lose, but he has to go through with this fight. I know people like that. I'm like that."
This was the first time that Slade had started a song from scratch based on a visual. He explained to Denver Westword that he wrote it, "mainly about the guy wrestling with his doubts. It's a scary thing to face your doubts, especially in a relationship." Slade added that what he intended to communicate was that doubts are okay. "Struggling in a relationship is okay," he said. "Wondering if there's somebody better is okay. Because then you choose to stay, instead of shrugging your shoulders, saying it's good enough. If you carry those doubts secretly hidden in the corner of your chest, they'll kill you. They'll kill everything, man."
The pioneering black American actress Lena Horne once said, "It's not the load that breaks you down, it's the way you carry it." Fray guitarist Joe King was thinking about that quote when he penned the song's bridge. He explained to Denver Westword: "She had gone into an industry that was not open to her being in a lead role and just the weight of going into an industry like that and being one of the first ones, she said something at one of the award shows, she said something similar, and it just kind of stuck with me and I couldn't let this idea go that we all have loads."
Another song inspired by a Norman Rockwell painting was "Dreamland
" the third single from Canadian alternative rock band Our Lady Peace's 2009 album Burn Burn