Born and raised just outside Peterborough in Millbrook, Ontario, songwriter Serena Ryder grew up listening to old Beatles and Leonard Cohen records that she found in her parents' collection. She started singing publicly as a young child and, having received a guitar from her father, began playing the instrument at the age of 13. Songwriting efforts followed. In 2002, the 18-year-old took several recordings from a live Quebec performance and packaged them into an official demo, which eventually made its way to CBC Radio and got Ryder an invitation to perform on-air. As luck would have it, musician Hawksley Workman happened to hear the broadcast, and immediately contacted the singer at the station to invite her to record an album on his Isadora label.