Her father was a lawyer; her mother went to law school when Shai was 6. “I didn’t make a conscious choice,” Littlejohn says about why she picked law as a profession. “My selection process was: the job was high-paying and there were lots of women [at the firm]!” After 14 years, however, it was time to pursue her “nagging bucket list thing.” She didn’t like her boss, her mother had brain cancer, and she felt, “this is the time….I don’t want regrets about not spending time with music.” Though Littlejohn had only played piano as a child and sung in a quartet, she knew music made her super happy. So she booked an unconventional summer vacation with The Berklee College of Music and eventually packed up for Nashville. “I was back to being a beginner,” she says. “I was writing songs and recording in the studio with top people. But I felt like I was the weakest link.” After a year spent touring as a musician, however, Littlejohn explains to CoveyClub founder, Lesley Jane Seymour, how she found her way back to balancing both professions plus a family.