One Of Rachel Zoe's 'Most Panicked Moments' Involves Britney Spears

Rachel Zoe may look calm, cool and collected, but even she has had stressful moments throughout her career as a stylist that she thought would cause her to never find work again, including one panicked instance with Britney Spears.

During Friday's (April 5) season three premiere episode of the Climbing in Heels podcast, host Zoe and producer Mary Elizabeth answered listener questions all about Y2K style and how trends today are leaning into the return of the controversial fashions.

Zoe has a personal connection to the era as her styling career really took off during the late '90s and early '00s, working with a lot of famous faces while she was still mostly involved in the music industry. Zoe called that time in her career a "blur" because of the how much the pop stars of the time were working as she had to style them constantly to keep up with their various promotions, tours and shows.

In the episode, she talked about some of her favorite celebs she styled and artists she worked with, including pop icon and "Y2K Queen" Britney Spears on the music video for her debut single "Baby One More Time," recalling how it was one of her very first freelance jobs after her boss called her for help.

"I went in and started just working on it, like pulling the clothes and doing the prep and being on set," she said, adding that she ended up working with Spears several times, calling her "cute," "bubbly" and "fun."

Zoe also shared how she was able to keep her focus on the first job and not be starstruck.

"I think at the time I was so obsessed with being great at my job that I never looked at stars as stars, if that makes sense," she said. "I don't think in the moment I knew or cared that much that it was Britney. I knew, but it was more that I was such a fashion girl that to me, if you were like 'you're going on set with Karl Lagerfeld and Kate Moss,' that would have given me a cold sweat panic attack."

Her experience working on the set was one of the reasons behind her decision to do freelance work because it made her feel "alive." However, she did share an anxiety-inducing anecdote of a time working with Spears where she thought her career was over and she would "never work again."

Zoe flew with Spears and her team to Monaco for a brief stint for the World Music Awards, but it was as trip with not much notice and she essentially had to pull an "all nighter" beforehand to prepare.

"I remember getting there and the management team going 'everybody break, take a nap, take a shower...' You know me, I don't nap, I don't sleep, but what did I do? I f---ing blacked out," she revealed. "I blacked out and the next thing I remember is security banging on my door telling me we had to leave, she was going on stage, I had to get her ready. I'm by myself, I had no assistant. That was one of the most panicked moments of my life."

On Climbing in Heels with Rachel Zoe, a weekly podcast from the fashion designer and author, Zoe chats with other businesswomen in various industries with different backgrounds as they discuss the challenges and successes of female entrepreneurship. Check out more episodes of the Climbing in Heels podcast at iHeart.com.