Jessica Simpson recently shared her journey as a pop star in the early 2000s, where she reflected on feeling inadequate in the music industry. Speaking at her concert at the Foxwoods Resort Casino in Mashantucket, Conn., the singer and entrepreneur revealed her struggles with self-doubt during her music career. Simpson expressed, “My whole music career, I had a job, and that was to be a pop star, and I tried. You see, when you’re younger, you never feel good enough, and it’s okay to not feel good enough.”
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After a 15-year hiatus from music, Simpson made a comeback in 2025 with the release of two EPs, Nashville Canyon Part I and II. These albums marked a significant return for the singer, who recorded them in Nashville and found solace in the city. Simpson spoke about her connection to Nashville, stating, “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. I just focused on that.”
The singer’s return to the stage after 15 years happened earlier this year at the Recording Academy’s Austin Chapter Block Party at SXSW in Austin, Texas. Simpson expressed the need to rediscover her true self and musical inspirations, away from external pressures. She mentioned, “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.”
In a candid conversation with Trailblazers Radio, Simpson shared about her challenging relationship with music after being dropped by her record label in 2008 following the release of her country album, Do You Know. The singer admitted to being “mad at music” at that time and recognised the importance of taking a break to realign herself. Now, with a newfound perspective and eight years of sobriety, Simpson is ready to embrace music once again.
Reflecting on her songwriting journey post-sobriety, Simpson acknowledged a significant shift in her creative process. She revealed how giving up alcohol helped her overcome fears and write music that felt authentic to her. Simpson 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.”
As Simpson continues to navigate her musical comeback, she remains committed to staying true to herself and her artistry. Her story serves as an inspiration for many aspiring artists facing similar challenges in the competitive music industry. Jessica Simpson’s resilience and determination to reclaim her voice in the industry showcase a powerful message of self-discovery and personal growth.