Influenced by singers like Rickie Lee Jones and Joni Mitchell,
Boyle joined various bands from age 17–19,
but these turned out to be unpleasant experiences ("folk bands, Rickie Lee Jones and stuff like that, all the angst").
In the intervening time, she performed assembly-line work in factories before ending up managing a pub in Sheffield. Meanwhile, she also recorded vocal samples for The Durutti Column, the Manchester-based musical project headed by Vini Reilly.
However, Boyle was considering a career in nursing by the time Kellett, who had heard the vocal samples pre-recorded onto a keyboard while playing live with The Durutti Column, contacted her about singing for the group he had formed with Taylor-Firth.
After auditioning, Boyle found in the band an ideal musical collaboration. Olive produced two albums from its inception in 1995 to 2000, after which the band ceased to work together.