At the age of 18, Naess moved to New York City to study music at New York University, she later switched her major, receiving a degree in anthropology. A resident of Greenwich Village, she began performing with her guitar at open mikes and was soon performing regularly in coffeehouses, bars and clubs like The Bitter End around Lower Manhattan, even busking at times. A friend, who was an intern at Sony Records, invited an executive to see Naess perform. Soon, a number of record companies were interested in signing her. She signed with producer Scott Litt's record label, Outpost Records, at the age of 22, shortly after graduating from NYU.

Naess began work on her first album in 1998. It was completed in June 1999. A series of business mergers postponed the album, meanwhile the Outpost label went out of business. The head of MCA Records, another division of the Universal Music Group of which Outpost had become part of, brought her contract over to MCA. Naess's first album, Comati