Jewel: A (Happy) Freewheelin’ Woman

Even though singer/songwriter Jewel has been noted as a particularly gifted writer for more than 25 years, she still found ways to explore new artistic territory with her thirteenth studio album, Freewheelin’ Woman, due out this fall. 

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“It’s the first time I ever challenged myself to write a record from scratch,” Jewel says. “I always have thousands of songs in my back catalog, and so I was always able to just instantly have at least ten songs that I was going to use for a record in any genre.” This time, however, she decided to do things differently. “I wanted it to be exactly who and where I was now,” Jewel explains.  

Lyrically, Jewel explores themes of independence, womanhood, hope, and heartbreak in these new songs. Musically, Freewheelin’ Woman is perhaps her most stylistically diverse album, encompassing folk, pop, and R&B. “The record is definitely showing influences I haven’t been able to pay homage to before,” she says. “A lot of the Muscle Shoals sound and Dusty Springfield and Sarah Vaughan—stuff that I was very obsessed with when I was between thirteen and fifteen [years old].” 

It’s been quite a while since Jewel’s last studio album, Picking Up the Pieces (2015), but she says this break was necessary: “I’ve always taken a lot of years between records when I feel like I need time to psychologically adjust or to creatively reload. I think writing, for me, evolves and changes. I have to have a lot of input. I like to read a lot. I like to experience a lot so I have new things to write about.” 

Jewel knows that this refusal to feel rushed may make her unusual in the music business, where artists are often pressured to produce new material at a rapid rate. But, as she points out, “This industry does not value whether you’re happy.” And she is unapologetic about making her own happiness a main priority. “I made myself a promise when I got signed to my [first] record deal when I was eighteen [years old] that my number one job would be to be a happy person, and my number two job would be to be a musician,” she says. 

“When I look back on my life, I want my whole life to be my art, and music is part of that,” Jewel continues. “Parenting has to be a part of that. Developing as a human has to be a part of that. I’ve always sort of made these what I call ‘deathbed decisions’—I pretend I’m on my deathbed and I’m looking back. Am I proud of who I am? One of my worst fears would have been to be on my deathbed and look back and go, ‘Well, I was super famous, but I was super unhappy.’ Or, ‘I was super famous, but I was a bad parent.’ And this job is kind of fraught with that potential.” 

It seems like Jewel has successfully navigated this path to happiness. Although normally based in Nashville, on this day she calls from The Rockies, where she’s been riding out much of the pandemic. In the background, there are joyful sounds of birdsong and her delighted young son playing with an exuberant dog. She seems relaxed and content. 

Things weren’t always so idyllic for Jewel, though—and she says that’s precisely why she was able to have such a mature outlook from an early age. “I was very aware, with the type of emotional background I have, that if I ever did become famous, it’s a pretty stereotypical ending for somebody like me…and that’s why I made that promise to myself, and that’s why I’ve led a pretty unusual career, I guess,” she says. 

Born Jewel Kilcher, she was raised in Alaska where she began performing professionally when she was still a child as a means to help supplement her family’s income. As a duo with her musician father, she frequently sang at gigs in bars and hotels around Anchorage. “It was like a blue-collar job,” she says. “Nothing glamorous.” 

Still, these shows were important because they revealed her striking musical abilities, and how others responded to her talent. “I knew that if I sang, I connected to people,” she says. “I knew that because I sang and I saw people respond to my emotionality. And so I just focused on that, and became incredibly stubborn about being true to what I was.” 

Jewel’s talent earned her a partial scholarship to study at the prestigious Interlochen Arts Academy in Michigan. “When I moved out at fifteen [years old], I knew kids like me become a statistic, and I didn’t want to be a statistic,” she says of seizing that opportunity. “The most rebellious thing I could do was learn how to be happy. The most counterculture thing I could do was learn how to be myself. I wanted to learn how to be happy, to feel free, to make choices that were my choices, no matter the situation.” 

This outlook was sorely challenged when, after graduating from music school, Jewel moved to San Diego and soon ended up in dire straits. “I was living paycheck to paycheck. I was very, very broke,” she says. Her job at a computer warehouse turned dangerous when her boss made sexual advances towards her. When she refused to give in, he retaliated by withholding her pay. This forced her into homelessness, and she began living out of her car. 

Even this terrible situation wasn’t enough to convince Jewel to compromise her values, though. “When that boss wouldn’t give me a paycheck, I was in a very bad spot, but I refused to let myself feel leveraged,” she says. Instead, she earned money playing solo shows around San Diego, singing and playing her acoustic guitar.  

“When I was singing in the coffee shop, it wasn’t to get discovered,” Jewel says. “I think that was one of the most misstated things, probably, in my career, is that I was living in my car for my [music] dreams. I was just living in my car so I wouldn’t have to have sex with the boss! It wasn’t anything more glamorous than that.” Still, she adds, “Don’t get me wrong—it didn’t mean I wasn’t ambitious. It just meant that I had a code or priorities I felt like I had to be committed and faithful to.” 

Record company executives soon took notice of Jewel’s heartfelt folk songs and distinctive, emotive singing style, and a bidding war ensued. Again, she showed a pragmatic streak by not letting herself get too swept up in the situation. “Grunge was everything—and I was not grunge,” she says of this era. “I was folk. I was earnest. Provocative, sure, in some songs. But I was sincere, and that was not cool. So there was this bidding frenzy over me, but I didn’t put a ton of stock into it. I felt like I had to be incredibly practical about how I made decisions, to make sure I didn’t end up on the street again.” 

The odds may have seemed against her, but Jewel’s 1995 debut album, Pieces of You, was an instant hit. Her first two singles, “Who Will Save Your Soul” and “You Were Meant for Me,” both charted in the U.S. and numerous other countries. Pieces of You went on to reach platinum sales 12 times, making it one of the best-selling debut albums of all time. Bob Dylan and Neil Young were so impressed, they both invited her to tour with them. 

Although this was an astonishing amount of success, Jewel viewed it with her usual maturity. “For me, I handled that overwhelmingly by being really intentional,” she says. “That made me feel I had a compass. It made me feel rooted. So my goal was not to be a famous person. My goal was to be an artist. Okay, that’s a little more doable. That’s within your purview.” This was apparently the correct path to take, as Jewel has gone on to release a string of acclaimed albums, earning four Grammy award nominations along the way. 

Jewel thinks the key to her longevity lies in her determination to stay true to herself, and her willingness to share that with the world in turn. “I think nothing’s more interesting than someone telling you the truth, and everybody’s truth is unique,” she says. “I think a lot of artists spend a lot of their creative energy trying to be like something else that’s popular when they could just focus on going, ‘What’s the most honest thing I can say?’ That’s a good use of your energy and it’s interesting. Have the courage to be yourself. Don’t let anybody tell you what you can and can’t do, or what your worth is.” 

“It’s a risk, for sure—but at least it’s a risk that leads to your own authenticity,” Jewel continues. “And I hope people can see that if you’re willing to live with nothing, you’re dangerous—in a good way. You can’t be leveraged. Nobody can out-negotiate you, and that’s a great thing. So even if you are destitute, even if you have no prospects, if you just keep investing in yourself and your authenticity and your integrity, to keep practicing whatever it is you are put on this Earth to do, you’re going to end up living a kind of magical life that will surprise you I think.” 

Photos by Dana Trippe.

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