Jewel photographed earlier this year in Los Angeles. Dana Trippe

After a megahit debut in the ‘90s, the singer-songwriter never stopped pursuing musical ‘growth and learning.’

The singer-songwriter Jewel wanted her album “Freewheelin’ Woman,” released in April, “to be fresh and representative of who I am today,” including her newfound feeling of “having more fun singing.” So she wrote a batch of new songs. That’s normal practice for most artists, but it was a departure for Jewel. On all 12 of her previous albums, she says on a Zoom call from her Colorado home, “I’d go through about 1,000 songs and pick what I wanted to use.”

Could Jewel, at 48, really have an archive of 1,000 songs that have never...

Could Jewel, at 48, really have an archive of 1,000 songs that have never been released?

“‘Writing has always just been what I do with my free time. I probably have 50,000 poems.’”

“Yes. I was always prolific,” she says with a laugh. “I had a couple hundred songs done by the time I got signed,” when she was 19. “Writing has always just been what I do with my free time. I probably have 50,000 poems,” she says. The dozen tracks on “Freewheelin’ Woman” were whittled down from more than 200 new songs.

Jewel’s current tour with the band Train, which runs through Aug. 6, is the latest stage on a long and winding musical road that began when she was 5 years old, performing with her parents in Alaska roadhouses. When she was 8, her parents split up, and she moved with her father Atz Kilcher from Anchorage to a homestead outside of Homer, with no heat or running water. (Atz and his extended family have been featured in the reality show “Alaska: The Last Frontier” since 2011.)

By age 15, Jewel Kilcher was living on her own. “I was very compelled to move out, but I was also realistic about what I was up against,” she says today. She found a job at a dance studio in Anchorage, where a teacher encouraged her to apply to Michigan’s Interlochen Arts Academy. She was accepted on the strength of an audition tape of French cabaret songs, but the partial scholarship she was offered left her with a tuition shortfall that was overcome with the help of a fundraising show and auction in Homer. Jewel went on to study operatic voice at Interlochen and has been largely on her own ever since.

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As a young artist, she was troubled by the knowledge of her “statistically low chance of success.” “My nurture was very poor,” she says of her family life, “and it made me curious about my nature. I knew that I had an emotional inheritance, which I worried gave me a predisposition toward abuse, drugs and outright unhappiness. That’s a daunting thing to confront at 15.”

By 1993 she had a regular gig at a San Diego coffeehouse, where a representative from Atlantic Records heard her sing and signed her to the label under the single name Jewel. Her debut album ”Pieces Of You” was recorded in a studio on Neil Young’s ranch and came out in 1995, when she was 20. When sales were disappointing, Atlantic told her to get off the road and start recording a follow-up album. But she was soon interrupted by an invitation to open shows for one of her heroes, Bob Dylan.

Jewel performing on stage ca. 1995, the year of her debut album, ‘Pieces of You.’

Photo: Jim Steinfeldt/Getty Images

A few days into the tour she was called to his dressing room, despite having been told to expect no interaction with the headliner. Mr. Dylan invited her to sing with him on his encore and quickly became a mentor, recommending books to read and music to listen to, as well as discussing her songwriting process. Most important, he encouraged her not to move past “Pieces Of You.”

“He liked what I did and he really felt I should stick with that album,” says Jewel. “It was an extraordinary, surreal experience that bolstered my confidence.” Buoyed by Mr. Dylan’s support, “Pieces Of You” eventually sold over 12 million copies, becoming one of the most successful debut albums ever. It stayed on the charts for two years, spurred by three hit singles, “You Were Meant For Me,” “Foolish Games” and “Who Will Save Your Soul.”

The latter song “was about taking accountability for my own happiness,” she says. “I wanted to feel like I was responsible for how my life turned out. I was learning to overcome this victim mentality. Yes, I had a tough childhood, but who cares? Nobody was coming for me, and nobody owed me anything. I owed myself something.” Wanting to help other kids from difficult backgrounds, Jewel helped found the Inspiring Children Foundation, a nonprofit devoted to the physical, mental and emotional health of at-risk youth.

“‘It’s very hard to be a musician and a mom, especially a single mom, because our jobs are by definition travel.’”

Looking back, she observes that her 20-year-old self would be shocked to see how much effort she devotes to juggling motherhood and making a living as a musician. Jewel has changed her touring schedule in recent years to accommodate her 10-year-old son Kase’s schooling, and she’s gone out of her way to mentor other musicians with children, to help keep them on the road and in the business. “It’s very hard to be a musician and a mom, especially a single mom, because our jobs are by definition travel,” she says. “It’s very difficult to navigate and requires thought and planning, but nobody talks about it because it’s not particularly sexy.”

The success of “Pieces of You” gave Jewel some artistic freedom, and she’s explored many genres, including spoken word, dance-pop, country and children’s songs. She’s appeared in films and TV shows and written two memoirs and a book of poetry. Last year, she won the reality show “The Masked Singer,” performing songs by Patsy Cline and Edith Piaf that highlighted her swooping range.

A willingness to take some risks in her career can be traced back to her interactions with Mr. Dylan and Neil Young, with whom she also toured early in her career. They imparted the idea that she’s not “entitled to comfort” and had to be willing to follow her muse, even in directions that didn’t lead to praise or recognition.

“I really value growth and learning, which is why I’ve always pushed myself to explore new genres,” she says. “That can be a difficult thing in a really public job, because growth is awkward and it’s imperfect, but it’s really what turns me on.”

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For Jewel, Stardom Was Just the Beginning