Ashlee Simpson Knew Who She Was After Seeing Sister Jessica Go ‘Through It’ in the ’90s

Ashlee Simpson is recalling her older sister Jessica Simpson‘s rough patch in the ’90s — and how she learned from her experiences.

In a cover story interview with The Cut on Thursday, Feb. 20, the sister duo recalled the start of their careers — and how difficult that time was for the “Take My Breath Away” singer.

“Let’s go back to you when you were signed. We’re in the ’90s. I was at the School of American Ballet,” Ashlee, 40, tells Jessica, 44, who noted that Ashlee also dyed her hair “with Kool-Aid.”

“I had braces, and I was just a little ballerina. You and Dad came to New York; you got signed. People were d—s back then,” said Ashlee. “It was like, ‘You should be skinny; you should look like this; you should sound like this person.’ I saw so much of that, and I was like, ‘Oh no, f— that. I’m never going to be that.’“

Then, Jessica commended her sister for knowing herself “from the beginning.”

Jessica added, “Yeah, you watched me going through it — you watched me getting booed onstage.”

Ashlee and Jessica agree that there was “so many men” in “suits” who would tell them “who you’re supposed to be.”

“I had to be a pop star because I signed on to be a pop star. No matter what, there was never going to be enough sales, there was never going to be recouping, because they would put so much into me trying to win. You’re a by-product of this company that’s making them money,” Jessica explained.

“I didn’t realize that until I was dropped in 2008 or ’09 by my country-music label with my first No. 1 country album. My country record was written in Nashville, and that’s where I felt very much myself,” she continued.

After the release of Do You Know, Jessica was presented with “360 deals” and she refused to sign.

“That was the first time I stood up for myself. But I was always defined by having a record deal. I had a record deal since I was 14 years old, so to be at the age of 28, 29 not having a record deal, I didn’t know where I was or what I was or who I was, and I didn’t know who I was working for,” she said.

She concluded, “It took me a while to realize that I deserved to work for myself.”

Now, Jessica is gearing up to release an EP titled Nashville Canyon Part 1 on March 21 and will be dropping the single “Use My Heart Against Me” on Feb. 21.

“I’d wake up in the morning and write down poetry, lucid dreaming style,” she told PEOPLE exclusively in February about the album. “And then bring that to the songwriting sessions.”

For “Use My Heart Against Me,” Jessica also said she “woke up with that lyric in my head.”

“It’s kind of craving someone that you want again and you don’t care if your heart is used against you – if it’s just for one night. Like, give it over, just for the experience again,” she said.