Jessica Simpson Reflects on Not Feeling ‘Good Enough’ as a Pop Star

Jessica Simpson opened up about her pop star past during a recent concert.

The singer, 45, was performing at Foxwoods Resort Casino in Mashantucket, Connecticut, on Sunday, December 7, when she began talking about how much she loved working on her latest music in Nashville.

“I do love Nashville. It brought me home to myself,” Simpson told the crowd, per social media footage shared by an attendee. “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, and just focus on that.”

Simpson went on to hint that she struggled with her self-esteem during her early years as a musician. (She signed her first record deal at age 17 and released her debut album, Sweet Kisses, two years later.)

“My whole music career, I had a job, and it was to be a pop star,” she said on Sunday. “And I tried. But I will say, when you’re younger, you just never feel good enough. And it’s OK to not feel good enough.”

Simpson made her return to music earlier this year after spending more than a decade away from the industry. She released the first part of her Nashville Canyon EP in March and performed her first concert that same month.

“Last night, was my first performance in 15 years,” she wrote via Instagram at the time. “It was an emotional coming back home to the best part of myself. Thank you for embracing me. You know that I have so much to say, but this lucky voice gets to soar again tonight. I love y’all. More to come…”

Six months later, Simpson released the second part of the Nashville Canyon EP, which she recorded with country veterans including JD McPherson and Sista Strings.

“It’s been so amazing to remove myself from my life as it was, because it’s hard for me to be creative when I’m taking care of everybody,” Simpson told Rolling Stone of recording in Nashville. “And it’s hard for me to convince myself that I needed to be selfish as a mother and as a business owner. I had to literally uproot myself.”

Simpson’s return to music came amid her separation from husband Eric Johnson, with whom she shares three children: daughters Maxwell, 13, and Birdie, 6, and son Ace, 12.

“Eric and I have been living separately navigating a painful situation in our marriage,” Simpson told Us Weekly in a statement in January. “Our children come first, and we are focusing on what is best for them. We are grateful for all of the love and support that has been coming our way, and appreciate privacy right now as we work through this as a family.”

One month later, Simpson praised Johnson, 46, for supporting her return to music.

“It is a gift. Eric supported that gift. My kids supported that gift,” she told New York Magazine’s The Cut in February.

Her pivot to country was actually inspired by a trip to Nashville with Maxwell, who requested an unusual choice of song for her birthday.

“Instead of singing ‘Happy Birthday,’ she wanted me to play Hank Williams’ ‘I Saw the Light’ when she woke up,” Simpson recalled. “I was having all these flashbacks of making my first record at 14, which was a gospel record, there. I was having flashbacks of writing In This Skin, writing ‘With You,’ some of my songs that reflect me more than other stuff.”