From Lawyer to Musician and Back with Shai Littlejohn * CoveyClub

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From Lawyer to Musician and Back with Shai Littlejohn


The Covey

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 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 how she found her way back to balancing both professions, plus a family.

Shai’s Top Tips for Reinventing in the Arts

  1. Save up for your dreams.
    If you have bucket list items, those don’t come free. And so to the extent that you can maintain some sort of income while you’re pursuing those things, I think it’s very important for peace of mind, for personal security. Or you have to have money saved. Especially because the older we get, the more responsibilities we tend to have. We have to be able to pay for health care, we need to go to the gym — there are things that affect our lifestyle that we definitely have to take care of financially. To this day, I maintain a very modest lifestyle in terms of the type of home I want to live in, the type of car I want to drive, because at any given time if I decide that there’s a dream I want to pursue, I don’t want my mansion to keep me from doing it. So there’s a give and take there.
  2. Art takes marketing dollars.
    It’s not about necessarily the talent — of course the talent is important — but it’s sort of smoke and mirrors. You’re led to think that because an artist is talented, it’s just gonna go viral. Everyone is gonna know it and see it. Living in Nashville, there are probably 10,000 songwriters who live within a 10-mile radius of me. I know countless guitarists, countless drummers. And I think when you’re in a community like this, you can see that talent is something you can throw a quarter at and hit in any direction.The difference is luck, being in the right place at the right time, being willing to network, being willing to ask people for help, being willing to collaborate and not be an island, thinking that your talent is so great that you’re gonna somehow shine. And you have to pay money to market.You won’t just get discovered. Maybe you keep your job because you decide that you need to pay for a publicist. A lot of people don’t realize when you see a “Best New Artists” list in a magazine, some publicist that a person pays a couple thousand a month has gotten them those placements.

    Even once you have these huge artists, when you realize the millions of dollars that has been put behind them. To get a number one song in country radio, it will cost you maybe a million dollars in promotional marketing to get that number one hit. It’s astronomical. And so the reason why you don’t have many artists in the music industry making it big is because they don’t have a million dollars in marketing to get a radio hit. I think artists do themselves a disservice when they think it’s all about their art. It’s not — their art is a product that has to be marketed, and once it’s marketed, it has to be received.


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