Lucy Kaplansky was just 18 when she moved to New York City, determined to become a singer. The city’s changed and so has she.

Over a cup of decaf at a cheerful, bustling Greenwich Village coffee shop, she remembers the surrounding area as “still pretty dystopian. ... It was slums and heroin and punk,” says Kaplansky, LAB’78.

But the city’s music scene was thriving. Gerde’s Folk City, the legendary club where Bob Dylan and Simon and Garfunkel got their starts, was undergoing a revival. Like many other young New York musicians, Kaplansky found an artistic home there. In the ’70s and ’80s, folk artists such as Richard Thompson, David Massengill, and Lucinda Williams made appearances at the club, alongside alternative bands including Yo La Tengo and Sonic Youth.

Between waiting tables and tending bar, Kaplansky earned a reputation at Folk City as a top-notch harmony singer and skilled interpreter of other people’s songs (she hadn’t yet begun to write her own). She enrolled at Barnard College, “but didn’t take it particularly seriously,” and left after a year. She performed in a duo with Shawn Colvin and lent backing vocals to Suzanne Vega’s “Left of Center,” which appeared on the Pretty in Pink soundtrack in 1986.

It wasn’t the kind of career Kaplansky’s parents originally envisioned for her, though they did share her love of music. Her father, mathematician Irving Kaplansky, who taught at the University from 1945 until his retirement in 1984, played piano and wrote witty math-themed songs not unlike those of his onetime student Tom Lehrer. (In retirement, Irving would make occasional appearances at Lucy’s concerts, accompanying his daughter as she sang one of his originals, “A Song about Pi.”)

For a time, music wasn’t the future Kaplansky saw for herself either. In 1983, just as her career was picking up steam, she abruptly put away her guitar and decided to go back to school to become a psychotherapist. It was a sudden decision driven by anxiety and quarter-life confusion, and one she questioned as her friends’ songs climbed the charts.

With support from her husband, filmmaker Richard Litvin, and her own therapist, Kaplansky made a gradual return to singing and writing songs in the early ’90s. Since then, she’s released seven albums and has performed all over the country, both as a solo artist and in the groups Cry, Cry, Cry with Richard Shindell and Dar Williams, and Red Horse with John Gorka and Eliza Gilkyson.

Kaplansky spoke with the Magazine about her career, her early performances at Lab, and how independent artists are faring in a changing music industry. Her comments have been condensed and edited.

Early music

Growing up I found a lot of solace in playing guitar and singing. I loved it. I would sit in my bedroom and write and sing and listen to Joni Mitchell and pretend I was performing.

I started performing at my summer camp and then at my eighth-grade graduation. I got enough positive feedback that I started to develop some confidence. Then I started performing at my high school.

There was a really great vocal teacher at Lab named Gisela Goettling, who was a German opera singer. I took a class with her when I was a junior.

I put on a show with one of my friends during Lab’s Arts Week, at the Little Theater. Mrs. Goettling came, and I thought, “Oh God, she’s going to hate the way I’m singing.” I’m not breathing properly and all that.

She came up to me afterward and said something along the lines of, “You have real talent.” I didn’t know that I did. She could have said anything, and she encouraged me. What a gift.

Scenesters

Folk City had been the center of a folk scene 15 years before and then it kind of petered out—now it was important again.

Everyone was just hanging around, wanting to get a record deal. Back then, there were no independent labels. It was Columbia, Warner Brothers, Arista. A few people did get signed. The Roches just exploded out of there. Steve Forbert had just been signed to Columbia when I got to New York.

I don’t know if there’s another scene that’s been like it since, where there’s one club, and everyone goes there every night.

Friendly rivalry

Suzanne Vega was also a student at Barnard at the time. They did a big story about me playing Folk City in the Columbia Daily Spectator and Suzanne told me later that her reaction was, “Who the hell does she think she is?” And I remember seeing her name on posters around campus and thinking, “She’s some nerdy folk singer.”

Then somebody put us on a bill together in a Barnard dorm show—that’s how we met. Then I told her she needed to come down to the Village.

Walking away

I got a gig singing in a country band in Norway for three months. It was wild, singing like six hours of country music every night.

When I got back from that trip I just decided, I don’t want to do this anymore. I was extremely confused and neurotic, mostly neurotic, and couldn’t let myself pursue this thing that I wanted and was good at.

I had started therapy at that point and decided to go back to college and become a therapist. Anyone who really knew me and knew what was going on said, “Wait a minute, why are you leaving this thing you want to do?”

Comeback kid

I was getting my doctorate, and I was not happy. Suzanne had this big hit, “Luka,” in 1987, and then Shawn won a Grammy for her first album. I was happy for them, and they were my friends, but I remember feeling so bereft, so jealous.

While I was in grad school, Shawn said, “Let’s make an album together. I’ll be the producer, you’ll sing, we’ll do it live in the studio.”

So we made this album [The Tide, 1994] when I was in grad school, but it wasn’t until I finished school that I finally figured out I really wanted to be a singer. Deciding to go back to music was the scariest thing I’d ever done, bar none.

Pen to paper

Songwriting feels so unpredictable. It almost feels like luck. I still struggle to write, and I don’t think of myself as a great songwriter, the way I think of Suzanne. I think I have some talent as a writer, but it’s taken years to get to that.

I still don’t know where these things come from. It doesn’t feel like, “I’m good at math; I can solve this math problem.”

When I became a mother that infiltrated my writing a lot. And when my parents started to fade, that was incredibly important to my work. So I started writing about different things. But it’s every bit as hard as it ever was.

Every time I sit down to write it’s this huge leap of faith, like, “Okay, this might totally suck, but if I don’t try, it will definitely not get written. If I do try, it might get written and maybe even be good.”

Kaplansky sings Kaplansky

My dad first and foremost loved math. That was what he loved from the time he was a little boy. But the story is that, when he was three, the whole family went to some Yiddish musical, and he came home and he played the main song on the piano. So his parents said, “He’s a genius. We’ve got to get him lessons.”

He took piano lessons for years and years, and he was good. In grad school, he would play in swing bands, making a little bit of money. When he was at the University of Chicago, he would play at faculty parties and stuff, and he was the rehearsal pianist for the Hyde Park Gilbert and Sullivan company. But he never wanted to do that over math.

My brothers and I learned a lot of the songs my dad would play—the Gershwins, Cole Porter, Irving Berlin, a lot of Gilbert and Sullivan. The joke was that my dad didn’t like anything from after 1950.

My dad wrote songs for fun—quirky songs. Some of them were about math. My brothers and I learned all those songs growing up.

Years later I said to my husband, “I need to come up with something lighthearted and fun to put in my show.” My husband, who has many great ideas, and this was one of them, said, “Why don’t you do one of your dad’s songs?” Now I always do one of my dad’s songs at my shows. People get a kick out of them, and I think it meant a lot to him.

Navigating the new music industry

It’s a very precarious time for people like me. I’ve always recorded albums that my record label would sell, and I would get royalties. That’s gone. CDs have stopped selling. I left my record label because there was no reason to have a record label anymore. So what is the new model going to be for someone like me? I will record somehow and put out music somehow.

One bit of good luck is that a year and a half ago, Spotify took a track of mine, “More Than This,” and put it on a very popular playlist of theirs. It got 11 million streams. That was this infusion of hope. I mean, they don’t pay what they should—it’s like a fraction of a cent per stream—but just the exposure was good.

It’s a new world, and people like me better embrace it in some way. I don’t know what the way is. I’m lucky. I have a career, people come to my shows, and I’m grateful for that. I’ll see how long I can make it last.