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Why Jessica Simpson never felt ‘good enough’ as a pop star

December 9, 2025
in News
Why Jessica Simpson never felt ‘good enough’ as a pop star

Jessica Simpson admitted that she never felt “good enough” as a pop star because she was so tough on herself in her “younger” years.

The singer took time to address the audience during her Sunday concert in Connecticut and reflect on how much she’s come since then.

“My whole music career, you know I had a job, and it was to be a pop star and I tried but I will say when you’re younger you just never feel good enough and it’s OK to not feel good enough,” she admitted.

Jessica Simpson performing onstage at Foxwoods Resort Casino Sunday
Jessica Simpson admitted that she never felt “good enough,” even at the height of her career, in a candid on-stage moment. Kevin Mazur/Getty Images for JS
Jessica Simpson performing onstage Sunday
The singer took time to address the audience during her Sunday concert in Connecticut and reflect on how much she’s come since her “younger” years. Kevin Mazur/Getty Images for JS

The “With You” hitmaker made a name for herself in the music industry at just 19-years-old with her hit debut single “I Wanna Love You Forever” and album “Sweet Kisses.”

Simpson went on to release several more chart-topping albums, including “In This Skin” in 2003 and “Public Affair” in 2006, cementing her as a true pop star.

While speaking to her fans, Simpson, 45, also hinted at the “hard time” she’s going through amid her divorce from Eric Johnson.

Jessica Simpson performing with a microphone during a summer concert.
“My whole music career, you know I had a job, and it was to be a pop star and I tried but I will say when you’re younger you just never feel good enough,” she admitted. AP
Jessica Simpson seated and smiling in a sequined dress with Levi's and Lifebeat logos in the background.
The “With You” hitmaker made a name for herself in the music industry at just 19-years-old with her hit debut album, “Sweet Kisses.” Luiz C. Ribeiro/New York Post

“I do love Nashville. It brought me home. To myself, it brought me inside of my heart, in a really hard time of my life. I just kind of had to surrender myself to my intuition, to the light that was in front of me, and just focus on that.”

The fashion designer spent a lot of time in Tennessee’s capital to work on her recent two-part EP, Nashville Canyon, which was inspired by the downfall of her marriage.

“Jessica has been working on new music for a while, but with everything going on now, she feels it’s the perfect time to go full force with it,” a source told Page Six exclusively back in January.

Jessica Simpson performing on stage, wearing a white corset, jeans, and a plaid shirt.
Simpson went on to release several more chart-topping albums, cementing her as a true pop star. Getty Images
Jessica Simpson performing with
She most recently made her transition from pop music to country with her EP, “Nashville Canyon,” which is inspired by her divorce from Eric Johnson. Instagram/@jessicasimpson

“She’s always journaling, and a few entries have evolved into songs about heartbreak and resilience. It’s been a very creative, albeit heartbreaking, time for her.”

The emotional music release — which marked her transition from pop music to country — was her first in 15 years, with her last album being 2010’s “Happy Christmas.”

Her track “Leave,” from Pt. 1 of the EP, suggests the former NFL player cheated on her with another woman during their marriage with scathing lyrics like, “What we had was magic / Now you made it tragic / Giving her what you gave to me.”

Jessica Simpson and Eric Johnson at the 2016 YMA Fashion Scholarship Fund Geoffrey Beene National Scholarship Awards Dinner.
While speaking to her fans Sunday, Simpson also hinted at the “hard time” she’s going through amid the split. WireImage
Jessica Simpson performing onstage Sunday
“I do love Nashville. It brought me home, to myself, it brought me inside of my heart, in a really hard time of my life,” she shared. Kevin Mazur/Getty Images for JS

Despite the fiery song, Simpson and Johnson, 46, have been spotted together multiple times since announcing their separation and just reunited for Thanksgiving.

“We were all together yesterday, over at my mom’s,” the Simpson told TMZ the following day. When asked if her ex was included, she replied, “Of course!”

“That’s my kids’ father,” Simpson noted, referring to their three children, Maxwell,13, Ace, 12 and Mae, 6. “Family first,” she added.

The post Why Jessica Simpson never felt ‘good enough’ as a pop star appeared first on Page Six.

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