It’s a dreary afternoon, so James Taylor is building us a fire. First he drags a bucket of kindling into the living room of his sprawling western Massachusetts house. Then he kneels on the rug in front of the hearth and begins, with deliberate precision, to chop up a few choice pieces of wood with a hatchet. Once the fire is crackling, he slowly unfolds himself into a standing position–all six-plus feet of him, still lanky and imposing at 71–and settles into a plush armchair. It’s the kind of scene that, in any other household, would be soundtracked by Taylor’s own music: the calming strains of “Carolina in My Mind” or the bittersweet tenderness of “Fire and Rain.”

That Taylor has ended up here–happily making music at the studio he built on this property, surrounded by his twin teen sons, wife of 19 years Kim, and an aging, wheezy pug, Ting–is more of a surprise to him than you’d think. Today, Taylor is a Grammy winner, Rock and Roll Hall of Famer and recipient of the Kennedy Center Honors and Presidential Medal of Freedom. But 50 years ago, when he got his big break with his celebrated album Sweet Baby James, he was a lost 21-year-old teetering between stardom and self-destruction. Now he’s looking back, excavating the dark corners of his childhood and youth in a new Audible Original memoir, Break Shot, that tracks his conflicted adolescence and path to becoming one of America’s most memorable troubadours. He’s also releasing his 19th album, a selection of acoustic reconstructions of old classics, many of them the Broadway show tunes on which he was raised.

Taylor has spent years trying to understand why the process of growing up was so arduous for him, attempting to “re-parent” himself–and figuring out how to do better for the next generation. “A sort of radical thing happened to my family,” he muses, “so I go back and re-examine it. How did this family–seemingly well-positioned–how did this family come off the rails the way it did?” It’s fitting that now his twin sons are about to leave home, their departures underlining his quest to set his own youth to rest.

Back by the fire, Ting waddles over to Taylor and nestles by the low coffee table, crowded with books. Across the room, a Steinway grand piano is masked by framed family photos perched on its glossy expanse. Taylor sips a glass of water, sedate and at ease, the very picture of boomer success. All that’s left is reckoning with the journey. “It has been,” Taylor says, “a very interesting trip.”

1971: Tops charts with Carole King’s “You’ve Got a Friend” Jim McCrary—Redferns/Getty Images

In 1971, Taylor was a soft-voiced, long-haired guitarist who hopped from New York to London to the Grammys, shying from fame even as it transformed him into an icon. But his path was not preordained. As a teen, Taylor was pulled out of high school and placed in a mental-health facility. “I luckily discovered music, and it sustained me,” he says. Taylor’s four siblings and parents were each struggling with their own addictions and distractions at the time too. “The thing is that teenage suicide is so tragic because it’s so preventable, and it’s not necessarily going to express itself again in your life,” he says. “I think that in America particularly we don’t pay enough attention to that period of time and how to shepherd young people through it.” Music saved him from his darkest impulses, but it was also a radical shift, taking him from a traditional life into the free-for-all of a creative career. “I basically stripped away all of my family’s expectations for me. I made myself free. It was scary. And it was dangerous too. The thought of one of my kids doing what I had done when I was 17 years old–” He whistles softly. Taylor headed straight to New York City’s East Village after graduating, ending up as a Washington Square Park busker. He leapfrogged soon after to the U.K., where the Beatles signed him to Apple Records, launching what would be a prolific career.

Ever since, Taylor has been a mainstay in American rock and pop culture. He worked with Paul McCartney, Carole King, Joni Mitchell and, famously, Carly Simon; he’s joined Yo-Yo Ma onstage and been featured with Ma’s bluegrass group for their Goat Rodeo Sessions, recorded at his studio. And he’s connected with the next generation, performing with Taylor Swift, recording a song with Charlie Puth and supporting Barack Obama at political events. He’s turned into a reliable mainstay of our musical culture, as well as the sound of lullabies and quiet evenings.

1978: Performs with singer-songwriter Carly Simon, then his wife Michael Putland—Getty Images

But mixed in over his early decades were regular relapses into addiction and bouts of treatment. “We get a certain programming by the way we’re brought into the world. Sometimes that programming is broken. It’s inappropriate, somehow; it doesn’t work. Then we have to examine ourselves and our upbringing, and become aware of it so that we can change it as much as is possible,” he reflects. That attempt at working through his weaknesses played out in public as his music. “It’s very self-centered, my art. It’s very selfish and personal. But this is what we do,” he shrugs. “What you learn is that everybody is self-involved. I think all life is. I’ve always just presented myself. Sometimes that’s embarrassing, sometimes it’s too much.” But most of the time, people have found solace in his tender, bleeding-heart balladry; his last album in 2015 bested even Taylor Swift, who was named after him, on the Billboard chart.

These days Taylor is given to creating art that goes beyond the personal. “That initial mission of self-expression that is so explosive and so powerful–that doesn’t last forever,” he says. Tumult has given way to craft. Earlier in the day, Taylor poured a cup of coffee–his third–and showed me around the barn studio he designed and built, all light timber and colorful tapestries. In the dripping forest outside, he said, he’d seen black bears and fisher-cats. Inside, the studio buzzed with crew moving gear through the lofted space, decorated with sidewalk art from a trip to Brazil, faded old couches and dorm-style lamps. Post-Its–rearranged track listings–filled whole walls, and a skeleton, twisted into a funny pose, perched atop the grand piano.

Taylor eagerly credits the A-list musicians he worked with in the making of American Standard, his new recording that rebuilds classics like “Moon River” and “The Surrey With the Fringe on Top” from the ground up. Taylor likes to talk about process; he lights up as he explains why these covers matter to him. “When you discover what the composer originally intended, and then when you take that further,” he explains, “there’s nothing that feels better.” He wants to keep these standards alive–because music, he insists, “is a human language that we manipulate, but it’s also true to the laws of physics. It gives our individuated consciousness–the prison of the self–the slip.” His compulsion to create was a life preserver as a teen, and still shapes him.

2015: Receives the Presidential Medal of Freedom Andrew Harnik—AP

Taylor’s understanding of music as a tool to manage mental health is particularly resonant right now. Much of today’s pop music is deeply confessional, outlining anxieties, fears and pain: a new generation using art as a way out. The psychological effects of the threats of climatic, economic and political instability are all over Grammy winner Billie Eilish’s haunted lyricism, Lana Del Rey’s nihilistic balladry and Mac Miller’s introspective darkness. Similar societal forces–the environmental movement, the Vietnam War, civil rights protests–also shaped Taylor’s youth.

After coming of age into the “postwar baby bubble,” he became part of “that big demographic thing which communicated through its music and its art and its FM radio–and did really think that the world could change. And we did change it. Maybe 5%,” he says. Taylor has never seen himself as a protest artist, exactly. But he has stood for a set of progressive values that America is currently debating, as it did in the 1970s. Right now, he’s incensed by inaction in the face of climate change. “I think we should ration electricity. Or energy,” he suggests. “The thing about protecting the earth, about the great environmental crisis of humanity and our being a scourge on the biosphere, is that it could bring us together. Just like the war effort of WW II. But Jesus, who knows.”

Spend time with Taylor and the hours slip away in these kinds of conversations, narrated by the gentle, gravelly tenor of his familiar voice. The fire burns merrily; his wife, whom he met when he played with the Boston Symphony Orchestra, where she worked, stops by to check on Ting and chat about their sons’ looming college applications. But mostly, Taylor wants to talk about music, what it means to be an artist and how grateful he is to have a career based on craft. “I never trusted the celebrity aspect. I knew that that was a trap, and inevitably it would betray you.”

“Of course,” he says, “there is an end to it. And the end is in sight for me; I’m 71.” He predicts his touring days will wind down as the decade unfolds. His predecessors Leonard Cohen and David Bowie have passed; his peers Paul Simon and Elton John are stepping back, a generation bowing out.

Yet as the day darkens to evening, Taylor still has plenty to say. What does James Taylor represent? He spreads his hands wide: he’s never tried to be anyone but a guy with a guitar and something to get off his chest. Now that the fire of youth is gone, what’s left is wisdom and warmth and a willingness to look back and try to make changes. “There’s only a limited amount you’re going to be able to do,” he says, “but it’s the only hope there is.”

This appears in the February 17, 2020 issue of TIME.

Get The Brief. Sign up to receive the top stories you need to know right now. Please enter a valid email address. Sign Up Now Check the box if you do not wish to receive promotional offers via email from TIME. You can unsubscribe at any time. By signing up you are agreeing to our Terms of Use and Privacy Policy . This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply. Thank you! For your security, we've sent a confirmation email to the address you entered. Click the link to confirm your subscription and begin receiving our newsletters. If you don't get the confirmation within 10 minutes, please check your spam folder.

Write to Raisa Bruner at raisa.bruner@time.com.