Jessica Simpson at the "All's Fair" Los Angeles series premiere held at DGA (Photo by JC Olivera/Variety via Getty Images)
Jessica Simpson opened up to fans during her December 7 concert at Foxwoods Resort Casino, sharing that she often felt “never good enough” during her years as a pop star in the early 2000s. Speaking candidly between songs, she described what it was like to navigate an industry that expected her to fit a narrow mold, and how those pressures shaped her sense of self.
“When you’re younger, you never feel good enough, and it’s okay to not feel good enough,” she said, reflecting on the emotional weight she carried at the height of her fame. Simpson explained that much of her early career was spent trying to live up to an idea of what a pop star was supposed to be, only to feel as if she constantly fell short.
Now, after a 15-year break from releasing music, Simpson has returned with two new EPs in 2025, Nashville Canyon Part I and Part II. She told the crowd that recording in Nashville played a pivotal role in helping her rediscover her voice and identity. “It brought me home, to myself,” she said. She added that the process forced her to trust her instincts again and focus on “the light” ahead of her instead of the expectations that once controlled her career.
Her return to performing began earlier this year when she took the stage at the Recording Academy’s Austin Chapter Block Party during SXSW. That marked her first public performance in 15 years. At the time, she said she needed to remember why she loved singing in the first place and let go of “who they told me to be.” For Simpson, reclaiming her artistry meant stepping away from the versions of herself the industry had crafted and reconnecting with the creative impulses that first drew her to music.
Simpson’s long hiatus began after she was dropped by her label following the release of her 2008 album Do You Know. She later admitted she was “mad at music” and needed time and distance to process years of exhaustion and frustration. The break allowed her to build a life outside the spotlight, confront personal struggles, and eventually find her way back.
A significant part of that journey included getting sober. Now eight years into sobriety, Simpson said the clarity that followed helped her overcome the fear she once felt whenever she sat down to write. Without alcohol, she explained, her creativity no longer felt clouded or forced. She could finally be honest in her music again, something she considers essential to her return.
As Simpson continues to perform and release new material, she’s leaning into the lessons she wished she had understood two decades ago. Her message to fans was clear: self-worth isn’t defined by an industry standard, and returning to your true self can often be the most meaningful work of all.
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