Across a recording career that’s spanned more than three decades, Callahan has become known for his insular self-sufficiency. Since abandoning his Smog moniker in 2007 to record under his birth name, his music has grown more sparse and stoic, a series of country landscapes with a bold, well-traveled narrator just outside the frame. As his voice has grown deeper and stronger, his lyrics have aged gracefully along with it. At their best, his records suggest an ongoing investigation into why we’re here, and what we’re supposed to know before we leave. On his last album, 2013’s languid Dream River, he presented a series of existential quandaries with zenlike resolve, as if he had been chosen to consult a higher power and bring back answers for the rest of us. “Is life a ride to ride?” he sang. “Or a story to shape and confide?/Or chaos neatly denied?”

It’s been nearly six years since he raised those questions, a veritable eternity in his prolific career. Since his earliest self-released tapes in the late ’80s—noisy, fragmented works of outsider art that bear no resemblance to his recent material—Callahan has maintained a ceaseless pace, never taking more than two years between records. This devotion has served as a guiding light through his body of work, which ranks among the wisest and most consistent among his generation of American songwriters.

“Music was all I had to do to feel like I was being a worthwhile human,” he says, looking back. “Then some things came along and made music not number one anymore… or, at least, put it in a three-way-tie for number one.”

In 2014, Callahan married Hanly Banks, a documentarian and therapist who directed his 2012 tour film Apocalypse. Bass arrived the following year. The family moved briefly to Santa Barbara, California, but Callahan found himself overwhelmed by the new surroundings and unable to focus. “When a cat walks into a room, it has to look all around and make sure it’s safe before it can curl up and go to sleep,” he explains. “I’m the same way.”

They moved back to Austin, and Callahan’s songs started flowing again. Where his last few albums unfurled painstakingly, like serene novellas, Shepherd is more like a scrapbook, filled with memories, sketches, jokes. The songs are shorter, and the guy singing them seems somehow closer—a byproduct of the album’s all-acoustic setting, and Callahan’s newly direct approach to writing. It’s what he calls a “real-life record.”

Callahan tells me he’s trying to be “more of an open book” in general, and many of these songs seem jarringly domestic coming from one of modern folk music’s most elusive wanderers. Throughout Shepherd, he uses the lowest, oakiest reaches of his baritone to acknowledge the renovators working on his home, or to briefly summarize a scene from “Sesame Street,” or to say things like, “I got married/To my wife/She’s lovely.”

As Callahan and I wander through a public park where he often takes his son to play, he speaks frankly about his romantic conversion. “Love is the answer to pretty much everything,” he says after deliberation, as if he’s genuinely considering the myriad questions it could solve. “If we can just love each other’s complete and utter humanness, that’s what everything boils down to, really.”

Callahan still speaks with veritable hearts in his eyes about his honeymoon in Kauai, Hawaii, which he calls the “best place on Earth,” and he rhapsodizes about his imagined responsibility to “bang the drum for marriage.” He even tries to cajole me into popping the question to my girlfriend in New York right then and there. “Come to Jesus,” he drawls. “I’m gonna get you to propose—on the phone!”

Passing a small garden, he stops to admire a bunch of bluebonnets and Indian paintbrush flowers. “Usually they come once a season, but it’s been so hot and cold here that they keep coming back,” he says. “It’s a new spring every couple weeks, and they bloom again.” We stop by a pond where three turtles are lined up statuesque on a log, and Callahan talks about wanting to spend more time around the house, tending his own garden. “I’d like to have a backyard full of watermelons,” he says.