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By marching to the beat of her own (synthesized) drum, the emerging pop artist won big on music’s biggest night. (Credit: Wikimedia Commons)

Contrary to the title of one of her hit songs, the party’s just beginning for performer Billie Eilish.

On what is billed as music’s biggest night — The Grammy Awards — the 18-year-old star won big. In all, she took home five awards, including the four biggest ones on offer: best new artist, record of the year, album of the year and song of the year.

It’s more than impressive — it’s historic. Eilish, who crafts dark, anti-pop dance music with her brother, Finneas, is now the youngest artist to ever snag album of the year. She is also the first woman — and only the second person in general — to win record of the year, album of the year, song of the year and best new artist on the same night.

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Then again, Eilish has always done things her own way. The Los Angeles native has established herself as much for her best-selling music — her platinum-selling singles include “Wish You Were Gay” and “Ocean Eyes” — as she has for intentionally offbeat style consisting of baggy clothing and a kaleidoscope of hair colors, atypical for many young celebrities. As this New York Times article points out, while other young female artists like Camila Cabello were “all va-va-voom curves and legs,” Eilish arrived at the Grammys wearing an oversized neon green suit, with two-tone hair and extra-long nails to match.

Her award-winning, rule-defying career got us thinking about bold women entrepreneurs who have similarly bucked tradition in favor of forging their own path. That’s often the riskiest route to take, but the payoffs can be huge. There are female founders like Chelsea Abingdon Welch, the pilot who launched a high-end watch company, and Gemma Young, who carved out a niche for herself in the U.K.’s male-dominated real estate industry.

And, of course, there are scores of women who are trailblazing by starting up in other, larger industries where men have also reigned supreme — both giants like tech, and growing sectors like cannabis and whiskey.

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Like Eilish, these women are succeeding by breaking molds, believing in their visions, and doing things in ways that defy convention. On Sunday, no one seemed more surprised than Eilish that this approach actually works. “I never thought this would ever happen in my whole life,” she said, during one of her acceptance speeches. Her brother also seemed stunned. “This is for all of the kids who are making music in their bedroom today. You’re going to get one of these.”

The takeaway? If you’re a non-conforming entrepreneur who’s breaking all the rules, you might just be onto something. Moreover, you might just succeed beyond your wildest dreams.

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