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Sheryl Crow
Credit: Monica Ahanonu

Sheryl Crow might be a nine-time Grammy winner with 10 studio albums, sell-out tours, and legions of adoring fans, but she’s followed an unconventional path to rock-star status.

Growing up in Kennett, Mo., Crow came from a long line of school teachers, so naturally, when she graduated from the University of Missouri, she went straight into the family biz. As an elementary school music teacher, she struggled to make ends meet. “I made $17,000 my first year of teaching, and $17,400 the next year,” she tells InStyle.

When she wasn't in the classroom, Crow played in a band, and serendipitously, her silky smooth vocals eventually caught the attention of an exec who was casting for an upcoming McDonald’s commercial. Crow booked the gig with the fast food giant and, in turn, earned her first big paycheck. “I went in, sang a jingle one afternoon, and made $42,000 in about 30 minutes,” she says.

Soon after, Crow left Missouri for L.A. to pursue her dream of singing professionally. She worked as a waitress to pay the bills while she promoted her music on the side. And then came the King of Pop.

“My big break came about eight months after I moved to L.A.,” Crow recalls. “I was recording a session singing backup, and I overheard some people talking about auditioning for Michael Jackson’s tour, so I found out where it was, crashed the audition, and wound up landing the job as one of his backup singers. It was absolutely crazy and one of those meant-to-be moments.”

Besides being a dream come true, the Jackson job meant a steady income. “I was renting a one-room apartment in L.A., waiting tables at a jazz club, and living check to check,” she says. “Finally I could afford things! At the time, my car had a boot on it because I illegally parked it so many times and I couldn't pay the tickets. When I landed that gig, I finally could afford to get the boot taken off of my car.”

Backup singing paved the way to full-on super stardom, of course, with her own hits like "All I Wanna Do" and "Soak Up the Sun" eventually climbing the charts alongside Jackson's. And though she's no longer scraping by, Crow says her working class roots have helped shape her entire philosophy about money. “I'm still that frugal girl from Missouri who was raised knowing the worth of a dollar,” she says. “My relationship to money is still ‘work hard, get paid.’

Sheryl Crow - Embed - 2
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There’s no mistaking that Crow is still working hard. Most recently, she dropped a new single, “Wouldn't Want To Be Like You” featuring Annie Clark a.k.a St. Vincent. She’s also still working on her next studio album, which she says may be the final album of her career. “I feel like it will be my last one,” she says of the project expected to drop in early next year. “I'll always release music. But I think our ears are built differently now. People don't sit down and listen to an album from top to bottom anymore. And I love the idea of being very immediate, making singles, and putting things out that way.” The album will feature women who have inspired Crow over the years too, like Stevie Nicks and Emmylou Harris.

When she’s not in the studio, Crow is pursuing other creative outlets, like designing her eponymous clothing and accessory collection, Sheryl Crow for HSN. “The line is very organic and fun to create,” says Crow, who shops her own closet for design inspiration. “I'm very drawn to vintage and denim — I wanted everything to have that American flair.”

Affordability was also an important requirement for Crow. Jeans clock in at around $100, while leather accessories like Crow’s best-selling Americana booties are priced under $200. “I hate how expensive clothes have become,” she adds. “I don't like spending $3,000 on a handbag, or $2,000 on a jacket. Every woman wants to look great, and it can be depressing when what you love is ridiculously overpriced. I wanted to make clothes that would look cool and edgy, and not break the bank.”

Keep reading for more from Crow, including her biggest money mistake, the importance of financial independence, and what she buys when all she wants to do is have some fun.

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On her financial upbringing… I grew up in a small town in the '70s where everybody was middle class. There might've been one or two families that made more money because they were doctors or had tons of farmland, but there weren’t really rich people. We were middle class too, and my parents worked really hard. We got an allowance, and if we wanted things we got summer jobs. They were great about getting us the things we needed, but if there was something we wanted, we had to buy it. I babysat to make money. It helped me buy my first car.

On teaching her sons about money… I wasn't a kid who got everything I wanted. I'm trying to raise my boys that way so that they understand that everything has worth and there are certain things you have to work for. I think it's valuable in this day and age because children are growing up with more at their disposal.

On her time as a teacher… I come from a family of teachers. I’m still very shocked by how little teachers make. Even though the argument is that you have two months off during the summer, teachers are spending more time with our kids during the school year than the parents are. We're creating the future of this country. I made $17,000 my first year teaching; when I sang a jingle I made $42,000 in one afternoon. I think our priorities are kind of wack. I figured out a way to live on $17,000 though. It really teaches you early on how to budget and live within your means. It's still a part of my core values.

On the importance of being financially independent… I think you create your own independence when you're able to manage your finances and live within your means. It's very stressful to be in debt. And now, so many kids are already in debt with student loans when they get out of school. I can't even imagine the pressure that brings. There's a lot of freedom in being able to manage your money, so you’re not just paying off the interest to the bills that you've run up.

On her favorite way to splurge… Oh my goodness. I have an 11-year-old and an 8-year old, so we like to do crazy, goofy stuff together. We're getting ready to rent an RV, take a vacation, and just drive around to places that we wouldn't go otherwise. Recently, we all got dirt bikes too. That was my last big splurge. They loved it. My role as mom is finding ways to keep my kids outside in nature as opposed to inside on video games. So anything that we can do that is outside and as a family is the best.

On her biggest money mistake… Like a lot of other people, I lost a lot of money when the market crashed. And that was a real turning point for me. I was never a risky investor, but from that moment forward, I realized whenever you're hoping to make more money off of the money that you've already made, like that ‘I want more, I want more’ greedy mentality, you're always putting yourself at risk. So now when I invest, I stay low risk. I put my money behind really solid investments. It doesn't feel natural to work this hard and lose a lot of money.

On knowing your own worth… We're entering a phase now where women are coming together and saying, ‘We demand equality.’ It’s so important to know your worth and demand that it be honored. And there are ways to put that across that are not overwhelming for people. You need to be articulate and organized in your thoughts. You have to treat other people with respect, so you can demand that respect back. And if you ever find yourself in a situation where you're not being respected, know that something better will come along. Don't kowtow to that. No amount of money is worth that.