Jessica Simpson is reflecting on her early struggles as a pop star in the 2000s, sharing candid insights into the feelings of inadequacy she experienced at the height of her music career. In a heartfelt moment during her December 7, 2025 concert at Foxwoods Resort Casino in Mashantucket, Connecticut, Simpson addressed her journey of self-discovery and her long-awaited return to music.

Early Career Struggles

Simpson, who first rose to fame in the late 1990s and early 2000s with hits like With You, recalled feeling constantly “not good enough” as she navigated the pressures of the pop music industry.

“My whole music career, I had a job, and that was to be a pop star, and I tried,” she said to the audience. “You see, when you’re younger, you never feel good enough, and it’s okay to not feel good enough.”

These reflections highlight the intense scrutiny young artists face in the entertainment industry, as well as the personal challenges Simpson experienced behind the scenes.

The Nashville Comeback

After a 15-year hiatus, Simpson returned to the studio and stage with two new EPs, Nashville Canyon Part I and Part II, released in 2025. Recording in Nashville helped Simpson reconnect with her musical roots and find personal clarity.

“I do love Nashville,” Simpson said. “It brought me home, to myself. It brought me inside of my heart in a really hard time of my life.” She added, “I just kind of had to surrender myself to my intuition, to the light that was in front of me. I just focused on that.”

Earlier in 2025, Simpson performed live for the first time in 15 years at the Recording Academy’s Austin Chapter Block Party during SXSW in Austin, Texas. She told Rolling Stone, “This time, I needed to remember who I was and why I wanted to sing in the first place and all the music that inspires me. And I needed to forget who they told me to be.”

Overcoming Personal Struggles

Simpson also shared how her music evolved following her decision to get sober. She admitted in a conversation with The Cut that songs written before sobriety often felt “not like me” and were too emotionally intense to release at the time.

“I have songs from those times that I never released because they just didn’t feel like me,” she explained. “Every time I would write, I was a little afraid of myself. It was almost too much, especially because I was drinking at the time. But once I gave up the alcohol, the fears just diminished. They went away.”

After being dropped from her record label following the 2008 release of her country album Do You Know, Simpson took a long break from music. Now, after eight years of sobriety, she is embracing her creativity and returning to the music industry with renewed confidence and authenticity.

Key Takeaways

• Early struggles: Jessica Simpson felt “not good enough” as a pop star in the 2000s.
• Comeback in 2025: Released Nashville Canyon Part I and II, returning after a 15-year hiatus.
• Nashville influence: The city helped Simpson reconnect with herself and her musical identity.
• Sobriety impact: Giving up alcohol allowed Simpson to overcome creative fears and release authentic music.
• Live performances: First stage performance in 15 years at SXSW Austin Chapter Block Party.

Simpson’s return to music demonstrates her resilience and growth, offering inspiration for fans who have followed her career for decades. Her story is a testament to the power of perseverance, self-discovery, and embracing one’s true voice.