How Do You Follow an Emotionally Wrenching, Surprise Breakthrough?

During a winter walk in Central Park in late 2020, Cassandra Jenkins made a confession to her occasional bandleader, Lola Kirke: She had sold much of her music gear and didn’t plan to return to the road.

A multi-instrumentalist and versatile singer, Jenkins had performed on stages for a quarter-century. Her parents had doggedly worked the New England hotel circuit as part of a trio that covered four decades of hits. As a teen, Jenkins and the family band played folk festivals, roaming in a hulking silver bus. After art school, she had balanced stints as an editorial assistant at The New Yorker, a farmer and a teacher with short gigs in so many bands she cannot remember them all.

It was draining. During a festival run in 2019, she’d maintained her sanity amid the throng by snapping a photo series called “Butts of Bonnaroo.” She had been set to tour as part of Purple Mountains, the band of Silver Jews’ David Berman, when he died by suicide days before it was scheduled to begin.

“I wasn’t quitting as much as letting go of the burden of certain expectations I put on myself in terms of how a career should look,” Jenkins, 40, said during a series of video interviews. “I was going to quit that narrow hope for a lot of mystery, a lot of unknowns.”

Jenkins had more news for Kirke: She had finished her second album, an idiosyncratic and frank reckoning with grief, disappointment and tenuous attempts to heal that she called “An Overview on Phenomenal Nature.” She was uncertain if she wanted to release it, but a little label had picked it up. She name-checked Kirke in the lyrics, so she said she’d send it over.

“I was gobsmacked, a perfect record,” Kirke said in a phone interview, recalling her first listen. “I wrote to her and didn’t hear back for a really long time. I knew she was being welcomed into spaces that should have welcomed her well before.”