Karen Chassie was born in London and moved to Manhattan with her family in 1974. As a young teen she became swept up in Rollermania and became an avid fan of the Scottish band the Bay City Rollers. She plastered her walls with Tiger Beat photos of Les McKeown, Eric Faulkner, Stuart Wood, and Derek and Alan Longmuir. She begged her mother to sew tartan fabric onto her flared, calf-length pants and begged her father for a guitar. She learned to play a little and wrote a song or two, but that was as far as it went; it was safer to lip sync to Barbara Streisand songs and Disco boogie around a locked bedroom.

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In the 1990s, Karen took a couple of years of piano lessons; her grandparents on her mom’s side were both pianists and were her inspiration. Finally, in 2015, her husband formed an accidental, local band with a group of neighbors and friends suffering the loss of their children to colleges around the country. They grabbed their instruments, picked their cover songs, and became known as The Penwoodys. Karen took up the ukelele and began singing and writing her own songs. She wrote and recorded her first song, Wish We Were Through, in 2017.