Mayfield first performed with her family bluegrass band One Way Rider at the age of 8. They began touring as a family band, boarding a 1956 tour bus (once belonging to Bill Monroe, Kitty Wells, and Ernest Tubb) and headed south from Ohio to Tennessee. At age 11, Jessica began playing guitar and writing songs. She asked her brother David to show her a few chords, and then she started using those chords to write her own songs.
Jessica got her first break at the Europe Gyro in Kent, Ohio playing for tips and free pizza every Monday. The place is known for its rough and unforgiving crowd and the experience toughened her act up considerably. For this residency, she had a fresh batch of songs she had just written after a breakup with her first boyfriend. It was then that she realized she had somewhere to channel her sadness: into her music.