Following her schooling, she moved to Los Angeles in hopes of starting a career in acting, but by 1992 she had moved to Nashville to pursue music. She worked odd jobs and played locally before taking a job as a songwriter for Polygram Records in 1997. Soon after she was overheard by the president of Giant Records at a local show, who signed her. The label released her debut in 2001, after she had scored two country radio hits in the U.S..
Middleman also co-wrote Radney Foster's 1998 single "I'm In," which was later released as a single by The Kinleys in 2000 and Keith Urban in 2009. She also co-wrote Tracy Lawrence's 2004 single "It's All How You Look at It" and Sarah Buxton's 2006 debut single "Innocence."
Middleman is a member of Blue Sky Riders, a country music trio also featuring Kenny Loggins and Gary Burr, her husband. They released their debut album, Finally Home, on January 29, 2013.

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