The Singing Lawyer

At, 39, Shai Littlejohn has been singing for practically her whole life, performing with various choirs and ensembles along the way. But she never took it seriously. “Music was always something that would help you be smarter,” she says. “I never thought of it as a career option, until I got older.”

Both her parents were attorneys and she always knew she would be a lawyer too. “I went to law school almost as automatic as going to high school,” she explains. “My dad kind of said, ‘You can do anything you want to do, after you go to law school.’”

Once Littlejohn’s law career was up and running it was difficult to find time for music. “It was too intense,” she says. “One of the directors would say, ‘Hey, can you come to this event?’ The next thing I knew I was working all day at my law job, and then at 8:00 p.m. they wanted me to be at some event, and that started happening two or three days a week to the point where I was exhausted.”

Finally, she had to give up singing in groups, immersing herself into a successful career as a political appointee in Washington, DC. At one point she was general counsel for the DC Sports and Entertainment Commission, a position that came to an end with the completion of the Washington Nationals ballpark.

She was then assigned by the political powers that be to help in various positions. That’s when she started to question how satisfied she was with a career where she was essentially being farmed out to clean up messes. “I decided to have a summer vacation, do something fun, and think about it,” she says. That was in 2009.

“I went to Berklee School of Music for a week-long summer program,” she says, recalling how she’d missed having music in her life. “I call it my rather unconventional summer vacation. I absolutely had a ball.”

Later, she was recounting to one of her friends what a wonderful time she had had at music school, and that she was waiting to take on her next legal assignment. The friend suggested, “Why don’t you go back to Berklee? You loved it so much,” recalls Littlejohn.

“While I was on the phone with her I was literally filled out the application, put my credit card in, and hit send,” she says. “When they offered me an audition, it was still just an adventure. I thought I would go to the audition and probably wouldn’t get in, but they accepted me.”

“When I got there it was super tough. I had no training in music theory, so I didn’t really have any foundation for Berklee. I think it was harder than law school and I almost gave up. At first, I was getting the lowest grades I ever had in my life. I put notes on my wall to myself: ‘you are not a complete failure.’”

“And then I thought, I don’t need a degree to be successful in music, I’m here to learn; it doesn’t matter.” But, putting her grades at Berklee in perspective was only part of the equation. “I was commuting back and forth to DC for my law practice, trying to study, and making excuses for missing classes,” she says. She was only able to maintain that lifestyle, financially and physically for one year, but managed achieve As and Bs in all her classes.

As a consolation she decided to a Berklee program that brings students to Nashville, where she discovered an alternative learning environment. “I ended up saying, ‘Forget Berklee, I can come to Nashville and it’s much cheaper than Berklee and I’ll just learn from the people around every time I come.”

So, began Littlejohn’s double life as student of the Nashville music scene and practicing DC attorney. “I’ve been going back and forth for about a year and a half now,” she says, of the two careers that have little overlap. “They are complete opposites. When you are dealing with clients you are on heightened alert at all times and constantly responding to questions. In Nashville, it’s nice to just have a free mind to create new songs.”

“When I come to Nashville, I probably work more hours than I do with my law practice, and that’s because I love it so much. It doesn’t feel like work. I’ll stay up to 3:00 a.m. to finish a song, and then I have this incredible sense of satisfaction,” she says.

But, she’s not ready to give up being a lawyer any time soon. “I don’t think I would ever stop being a lawyer, even if I were to have success in pitching songs,” she says, explaining that she also has a passion for her legal career, though she’d one day love to move her practice to Nashville. “I just happen to love contracts and negotiating contracts, and I think that’s something I would do forever.”

Among her personal music goals she hopes to one-day license some of her songs to other artists, and have a chance to play with her idol. “This may sound crazy, but I would really like to sing with Vince Gill some day,” she says, adding, “on the Grand Ole Opry stage, by the way, that would be a dream come true.”

Littlejohn has found so much joy from getting back into studying and playing music, that she is eager to encourage others to do the same. “Just like anything, if you are proficient at it, it can be more fun because you have the tools.”

She recently released the self-published ebook Quit the Firm and Join the Band, encouraging others to follow their passions and make them happen. “My message is: what’s stopping you? Find the courage to move toward something that you really want to do. It doesn’t have to be drastic. ‘Quit the Firm’ stands for quitting a certain mentality—I can’t do it, I’m too old to do it, I don’t have the money. If you want to do it, you have to find a way.