Jessica Simpson opens up about early insecurities as a 2000s pop star

At a concert on December 7, 2025, in Connecticut, Jessica Simpson spoke candidly about the emotional toll of rising to fame in the early 2000s, admitting she never truly felt “good enough” to be a pop star. “My whole music career, you know, I had a job, and it was to be a pop star, and I tried,” she told the audience. “When you're younger, you never feel good enough, and it’s okay to not feel good enough.”

Simpson’s honest admission highlights the pressure many artists face behind the gloss of success. She recalled how, for years, her career felt like a job rather than an authentic creative journey, a struggle that ultimately limited her connection to her music.

After stepping away from the spotlight for 15 years, Simpson has returned with renewed purpose. In 2025, she released two new EPs , Nashville Canyon Part I and Nashville Canyon Part II, and credits her time in Nashville for helping her rediscover herself. The city, she said, “brought me home, to myself,” during one of the toughest periods of her life.

Simpson also opened up about how sobriety and the passing of time transformed her approach to songwriting. Having reclaimed control of her creative voice, she’s now embracing vulnerability and authenticity in her music, a stark contrast to the image‑driven pop‑star persona she felt she had to maintain in her early career.

Her comeback isn’t just a return to music; it’s a reclamation of identity, purpose, and artistic integrity.