Polly Singer is the designer and CEO of Polly Singer Couture Hats & Teas — and by her own admission, she never saw this coming.

She grew up in small-town Kentucky, and the path that led her here wound through some pretty unexpected places. For eight years, Polly worked in the music industry in New York City, assisting with concert tours for artists like U2, Bruce Springsteen, Van Halen, and Tom Petty, and later worked at Sony Music, Radio City Music Hall, and EMI Records. Along the way, she earned gold and a platinum records for her work on Harry Connick’s When Harry Met Sally soundtrack — something she’d always dreamed of and could finally check off her list.

It was during her time at EMI that Polly realized she needed to create something with her own hands. A friend encouraged her to enroll at the Fashion Institute of Technology, where she nearly quit after her first class. But she signed up for one more — bridal millinery — and everything changed. She went on to earn a certificate in Millinery Design, often staying up past midnight to finish pieces while balancing a full-time job. Becoming a fashion designer was the last thing she had expected.

That was over 33 years ago. Today, the studio is in Kentucky, the hours are still long, but she wouldn’t change a thing.