In high school Wilkes joined a pop/rock band, High Flight Society, and toured with them for 12 years. In 2010, country artist and Wilkes' former classmate, Sam Hunt, asked High Flight Society to accompany him on tour. That same year, Wilke's daughter, Linley Jane, was born, but after a while the strain of having a family and being on the road led Wilkes to leave. Currently, Wilkes writes country music for a Nashville publisher while taking care of his wife, Chelsey, who suffers from lupus. Wilkes writes country songs but wants to get back to his pop/rock roots.