[2] At first she was primarily interested in rock music, but she discovered jazz after hearing guitarist Wes Montgomery on the radio.

[4] In 2001, Bailey she released Reunion of Souls with guitarist Chris Bergson, Ashley Turner, and Sunny Jain.

In 2006, Bailey released Live @ The Fat Cat and was a headline act at the Pittsburgh Jazz Festival.

[7] In the August 10 edition of DownBeat, reviewer Phillip Booth called Bailey "one of the new greats of her chosen instrument".

She has taught at Berklee, summer workshops at Stanford University,[3] and the Collective School of Music in New York City.