I discovered this song through John Mayer a while back. He wrote about it on his website. I followed everything JM did back then so naturally I’d be inclined to listen to any artist he suggested I listen to. He definitely had some good picks!
“How Much It Hurts” is all about pretending you’re fine on the outside while hurting on the inside. Sometimes it’s healthy to just get the words off your chest and say them out loud whether or not anyone is listening. Sometimes music is the only way to communicate. I’m sure the message in this song was well received.