Anderson and Dillon didn't know each other very well prior to penning this song, so they started off their session by having breakfast together, and talking about their lives. Anderson admitted to The Boot
that he was envious of Dillon.
"He had, kind of, what appeared to be, a carefree life, and I had had more of an uptight life," he explained." Before we even started writing the song, I said the opening line to him. I said, 'You know, I kind of envy you in a way. I wish I had gone out in the rain without an umbrella over my head a bunch of times,' and that's the opening line to the song: 'I'd spend a lot more time out in the pouring rain without an umbrella covering my head.' And that song just came out; that song just flowed, and we probably wrote it in a couple hours."