Robert Pollock Jr., who goes by Robbie, wasn’t your average kid growing up.

The young Robbie was a loner who took guitar lessons and played in his mom’s church band. But he’s quick to add he was also well-rounded, riding bikes and skateboards. So when kids in his neighborhoods of South Jamaica or East New York mocked him, “none of it stuck.”

Despite being “not very good at all”—by his own estimation—at guitar, he showed how much he didn’t care about their opinion by turning the music-nerd stereotype upside down, coasting through Brooklyn on a skateboard with a violin in tow.

“I really wanted to learn the violin because I got Vivaldi’s Four Seasons on a cassette tape at Odd Lots for cheap,” he says. Something appealed, he added, about the instrument’s bleeding-heart sound.

Pollock is expressive and thoughtful, a creative thinker you can feel writing songs about the world around him as he talks. But he says reading music or transposing weren’t his gifts. At 16, he gave up on the guitar. He played that violin for six months, then left it behind when he moved out of his mom’s place at 18.

But his ear for music stayed with him. In his 20s, he shared a Manhattan apartment with a guy from Minnesota who favored Brad Pitt and performed on the street and in subways for money. “He would write songs that were rambly with no hook to speak of,” Pollock says.

This inspired him to see if he could write something better. Pollock started practicing and performing in open-mic sessions around the city. By all accounts, he was growing out of that teenage loner status. Then one night, he says, he had too much to drink and committed the crimes that landed him in prison. Eventually, he found himself at Sing Sing Correctional Facility serving a decade-long bid.

While on the inside, his mother sent him the guitar he asked for, and slowly he returned to making music. Though there were many things from which he was kept from doing, he was surprised and delighted to find that he could keep his guitar with him and strum softly in the dark.

Pollock had written more than two dozen songs and was playing with multiple bands by the time he learned about the Musical Connections bi-monthly musical workshop at Sing Sing. “I participated in the workshop’s first season, which was new to all of us and to the facility,” he says. “It was groundbreaking and totally unprecedented.”

In Musical Connections, men refine their compositional and instrumental skills, then perform their original works. When they return home, they continue to inform Musical Connections as part of an advisory committee, meeting regularly to support one another while also making music.

This year marks the 10th anniversary of the program at Sing Sing, supported by the Weill Music Institute—the social impact and education arm of Carnegie Hall—in partnership with the New York State Department of Corrections and Community Supervision.

It was auditioning for his friend and mentor, Kenyatta, in the program that helped Pollock face his greatest fears, vulnerabilities, and stumbling blocks in performance: himself.

“Before I joined the group, I was a fraud. I navigated a lot of worlds without being deeply involved,” Pollock says. Up until he got up on stage, “my whole survival in prison was based on anonymity and lies, which, by the way, is not conducive to personal change. I felt like I was the worst person in the world based on what I had done, but I realized that other people felt that way based on what they had done, too. Everyone carries shame. I started looking at it like, ‘I may always carry this shame, but the only way to deal with this is through honesty.’ It was the single most terrifying experience.”

That experience allowed Pollock to create community bonds, and to learn more about music and himself than he ever had. The first season of Musical Connections helped “it all get sharper,” he says. “I practiced religiously. It was my therapy—that experience of being valued for my contributions, that spirit of congeniality.”

“My last concert at Sing Sing, Clive Gillinson—Carnegie Hall’s executive and artistic director—saw me perform a song called ‘Duke Did It.’ It’s a multifaceted song, intended to evoke an ambiguous feeling.” Inspired by Duke Ellington, the piece was part of a yearlong exploration of Ellington’s Sacred Music. After Pollock’s performance, Gillinson was anything but ambiguous when he approached him. “He told me, ‘This is so good it needs to be heard on the main stage at Carnegie Hall.’”

Pollock’s personal review of his performance of “Duke Did It” was mixed. “That project taught me what it takes to prepare to be part of an ensemble. I previously failed spectacularly in many performances, and not just in the sense of ensemble participation,” he says with a smile. “I screwed up in songwriting and vocal chops, style and message, but I accumulated knowledge and a kind of fearlessness.”

In the end, for him, Musical Connections was about more than the music. Once Pollock got started in arts programs, he couldn’t get enough, eventually becoming involved in several. He says he’s addicted to how art can transform people—that a creative community can offer something few people know better than he does: life experience.

Last spring at Carnegie Hall, vocalist Sarah Elizabeth Charles joined Pollock in a performance of “Testify”—one of his own compositions that was chosen to be featured in A Time Like This: Music for Change, the culminating concert of the Weill Music Institute’s creative learning project. “I’m still discovering what Musical Connections is,” he says. “I feel connected to it because I feel like I need it and because I feel a responsibility. I have to fight for the time when I go meet with the other guys. We may musically produce little or nothing of value—I still don’t feel like a super great musician myself—but I’m there with my people.”

For more on Musical Connections, visit carnegiehall.org/MusicalConnections.