Amid an unfortunate setback while touring, the wheels of Imaginary Music were put into motion. During a stopver in Texas with Shallou and Blackbird Blackbird, their van was broken into and everyone’s equipment was stolen. This included Hugo's laptop which contained the bulk of a new album. Thanks to the generosity of fans the tour continued with borrowed gear, but the music was unrecoverable.

Hugo eventually returned home to Oxford, England, where he started writing the record from scratch. But instead of trying to recreate the lost material he took a concept-driven approach, opposed to his traditional autobiographical method. In an attempt to understand the art of timeless pop music, a new album emerged. Sonically, the record channels the hyper-romantic music of the 80s, citing inspiration in China Crisis and Prefab Sprout, as well as less esoteric artists like Toto and Heart. The writing and recording was an almost entirely solitary exercise, allowing Hugo to fully embody the imagined pop artist in his mind’s eye.