The aim of this thesis is to explore how adopting a playful approach to contemporary popular music making influences creative flow within that context. In order to achieve this aim three component factors derived from the intersection of the scholarly humour, creativity, and play literature––frame of mind, flow, and playfulness (PF)––have informed a single unifying theme I call the “playful frame of mind.” Contemporary popular music makers live in an era where an over-abundance of affordable technological aids (along with the distribution capabilities of the internet) have created a glut of creative possibilities, and along with it an ever-present risk of cognitive dissonance caused by their “noise.” Such technology brings creative options to all and sundry once reserved for a few rock star elite signed to multinational record companies. It is now possible for every part of the popular music-making process to be performed, or enhanced, within a software context. Nonetheless, popular musicians today still operate according to paradigms largely informed by epoch-changing, post-War recording artists such as Elvis Presley, Bob Dylan, The Beatles, and The Beach Boys. The technology used for doing so may have progressed, but the basic rules (and roles) of the game have remained the same.