Jessica Simpson Shares Her Journey of Self-Acceptance in the 2000s Pop Scene

Jessica Simpson at the Foxwoods Resort Casino.
Credit: Kevin Mazur/Getty

NEED TO KNOW

• Jessica Simpson recalled feeling “not good enough” during her early career as a pop star.
• In 2025, she returned to music with two new EPs, Nashville Canyon Pt. 1 and Nashville Canyon Pt. 2.

Jessica Simpson has opened up about her early experiences as a pop star during a concert on December 7 at the Foxwoods Resort Casino in Mashantucket, Connecticut.

The singer shared her struggles with feelings of inadequacy as she began her career in the music industry. “My whole music career, I had a job, and that was to be a pop star, and I tried,” Simpson said. “You see, when you’re younger, you never feel good enough, and it’s okay to not feel good enough.”

Jessica Simpson.
Credit: SGranitz/WireImage

In a significant return to music, Simpson released two EPs in 2025, titled Nashville Canyon Pt. 1 and Nashville Canyon Pt. 2, the first albums she created after a 15-year hiatus. She expressed how the city of Nashville played a crucial role in her transformation during this period. “I do love Nashville,” Simpson stated. “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.”

Jessica Simpson at Foxwoods Resort Casino on Dec. 7.
Credit: Kevin Mazur/Getty

Earlier in the year, Simpson performed on stage for the first time in 15 years at the Recording Academy’s Austin Chapter Block Party during SXSW in Austin, Texas. During her performance, she emphasized the importance of reconnecting with her identity, stating, “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.”

Simpson had faced challenges in her career, including being dropped from her record label after releasing her 2008 country album, Do You Know. In a conversation with Trailblazers Radio, she admitted to feeling “mad at music” and needing a break. Now, after a 15-year hiatus and eight years of sobriety, Simpson is ready to re-engage with her music.

Reflecting on the evolution of her songwriting since achieving sobriety, she explained, “I have songs from those times (before her sobriety) that I never released because they just didn’t feel like me. 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.” She concluded, “But once I gave up the alcohol, the fears just diminished. They went away.”