For about a decade, Jeffrey Silverstein has been veering back and forth between his day job as a special education teacher and his lifelong pursuit of making music—not entirely out of necessity, but also because doing so provides him with a bit of personal harmony.

“As a teacher, you fall into the rhythms of the seasons and the school year. I kind of like that,” he told the Mercury. “There’s a really beautiful balance that comes along with it. You have pretty clear windows of when you’re teaching, when you might tour, or when you might have a little bit more headspace to write and record.”

In recent years, however, growing interest in Silverstein’s brand of pastoral, ambient-influenced folk music has threatened to throw off the balance. That wouldn’t be a bad thing, necessarily, but it does put the Portland-based songwriter at a crossroads.

“Everyone’s got their own version of success, and I’m trying to stay focused on that,” Silverstein said. “But as things move, the call to pursue music in a more full-time way is really present for me. I don’t know exactly what that looks like, but I know something’s happening and I’m trying to listen.”

This is not the first time Silverstein has enjoyed musical success. Originally from New Jersey, he spent his post-college years in Baltimore, where he played in a band called Secret Mountains. He learned to book shows while soaking in the city’s music scene, which at the time included up-and-coming acts like Dan Deacon, Future Islands, and Beach House. His next stop was Brooklyn, New York, where he formed an indie-folk duo, Nassau, and earned his master’s in special education.

He didn’t sing in either of those bands, however, and when he arrived in Portland nearly six years ago, Silverstein was unsure of his next musical step. On a break from school, he participated in an artists’ residency at the Sou’wester Lodge in Washington, where he recorded and performed a handful of songs that gave him the confidence to pursue solo music.

“That experience was a real decision point for me,” he said, “and it gave me a little jolt, like, ‘OK, I can do this myself.’”

Silverstein’s first album under his own name, You Become the Mountain, came out in April of 2020, and its mellow, meditative vibe proved to be a balm for those isolating at home, stuck online, and seeking comfort, as the world turned scary in a whole new way. He followed that up a year later with the Torii Gates EP, which, like the debut, featured Silverstein’s wandering guitar work accompanied by local pedal steel guitarist Barry Walker Jr., bassist Alex Chapman, and the gentle pitter patter of a drum machine.

Earlier this month, the Athens, Georgia-based Arrowhawk Records label released Silverstein’s second full-length, Western Sky Music, a nine-track collection of cosmic country and shimmering Americana that feels like a significant step forward from his previous work. There are a few different reasons for that, including the addition of a drummer, Dana Buoy, formerly of the experimental band Akron/Family.

“There’s more trust in my process. I have a stronger belief that when I sit down to an instrument now… something will come out,” Silverstein said. “Another part of it is that Dana and Alex live (very close) to me, so I’ve gotten to spend more time in relationship with them, not just as musicians but as friends, too.”

Buoy not only brings live drums to Silverstein’s music, he also has a sharp ear for arrangement, so he and Chapman help Silverstein corral ideas into more traditionally structured songs. Add Walker Jr.’s prominent pedal steel licks to the mix, and you end up with tunes that feel alive, sturdy, and self-assured, with forward momentum embedded in their burbling grooves and more country influence than ever before.

Western Sky Music is twangy, to be sure, but Silverstein finds country music’s influence on his own work in a less obvious place: his vocals, which are often more spoken than sung—giving him space to play with language and shade the mood of his songs.

“There can kind of be this lightness and darkness to the words, and I like that. I like songs that can be pretty plain-spoken and country is a really good avenue for someone with my type of vocal register and delivery,” he said.

The simple fact that Silverstein is singing—and talking about singing, and hearing from others about his singing—is proof that he has come a long way in his musical journey, and that he’s not done yet.

“I just felt really strange about my voice for a long time, so when people come up to me and speak highly of it, it’s like, ‘Are you sure?’” he explained. “But it’s wonderful that people are connecting to that part of my music, or connecting to my music at all.”

Jeffrey Silverstein opens for Fruit Bats at Revolution Hall, 1300 SE Stark, Thurs May 25, 8 pm, $25-30, tickets here, 21+