How Jessica Simpson Follows Her Intuition to Grow Her Business

Jessica Simpson has always spoken from her heart. Whether belting out her popular songs on stage, being her true self on TV, or regaining the reigns to her business, The Jessica Simpson Lifestyle Collection, she listens to her gut instincts, takes time for herself, and leads with small steps that build confidence. In a recent Office Hours episode, Simpson explained that it’s really those small wins that matter most – especially when something seems impossible.

In 2021, Simpson took a larger leap: she bought back her namesake billion-dollar brand from the licensing company that previously owned a majority stake. Now, she’s using her strength and authentic voice to guide the Jessica Simpson Lifestyle Collection into a label that encourages people to lead happy, confident, inspired lives.

Here’s how Simpson used her intuition to take back control of her business, and make it shine even brighter than before – one step at a time.

There’s beauty in making small goals because once you achieve them you gain more confidence. Your next goal can be bigger. It’s those small accomplishments that give you value within yourself.

—Jessica Simpson, owner, The Jessica Simpson Lifestyle Collection

1. Trusting Her Ideas

The idea for launching a fashion brand started with Jessica’s music, TV, and film career. Fans loved Jessica’s style choices, especially her Daisy Dukes and cowboy boots after playing Daisy in the “Dukes of Hazzard” movie, as well as her casual outfit choices on the TV show “Newlyweds.” Whatever Jessica naturally felt like wearing, her fans wanted to wear it, too. Even in her #1 Billboard song, “With You,” Jessica sang about feeling beautiful wearing a T-shirt.

“It’s nice to be glam, but also good to see what’s behind the glamorous,” Simpson said. “If you can make a T-shirt glamorous, that’s who I am – that’s the DNA of fashion for me.”

At that time, most celebrity brands were collaborations rather than solo ventures, she noted. Her team, which included her parents, didn’t know if having a fashion brand would work. But Simpson, already a style icon, also found inspiration from the styles she saw fans wearing while on tour. Being observant and connecting to her fans proved powerful, and she built the brand into a shoe, clothing, and handbag staple that reflected her own style and her community of fans.

“Most of the time I feel like if you’re focusing on who your audience is, those people are the ones that relate to you,” Simpson said. “I didn’t know it would be what it is today –  that we’d still be going so strong – and that I’d one day be able to own it all. We win when we’re authentic to who we are.”

2. Taking Care of Herself First

To make sure she listens to herself, Simpson sets aside time for journaling. That has helped her find her voice, both personally and professionally, and even led her to write the New York Times best-selling memoir, “Open Book,” she said.

“It was really to let you in on who I am and who I always have been – growing up, the challenges I’ve faced, the pain I’ve gone through. You can see all the stories of my life woven to get to where I’m at right now,” Simpson said.

With health and wellness a key part of her life, Simpson wants to expand her namesake brand to offer products that help people lead healthier lives – both inside and out.

“I want people to feel great – I want people to love themselves,” Simpson said. “I want people to have that confidence to go out there and do the things they want to do, but they think they’re not good enough for.”

3. Celebrating the Small Steps

Celebrating small wins is important in reaching larger goals, according to Simpson. It’s how she’s built her successful career so far.

“I’ve always set small goals in my life,” she said. “There’s beauty in making small goals because once you achieve them you gain more confidence. Your next goal can be bigger. It’s those small accomplishments that give you value within yourself.”

It’s also important to pause and listen when you feel inspired, she added. That helps you find the next great idea to work toward.

Ultimately, trusting your voice and purpose, taking care of yourself, and following through, even in small steps, can lead to success. Being authentic throughout every step is the most important thing, according to Simpson.

“You can’t be a leader if you’re afraid to be yourself. You can’t be a business owner if you’re afraid to be authentic,” she said. “Fear has to be set aside. It’s taken a long time for me to own the Jessica Simpson Collection. Now that I have the power to own that, there are so many things we want to do.”

Next, the brand will evolve into a larger lifestyle company, with health and wellness products, home goods, and more on the way. Wherever the road goes, it will be fully true to Simpson and her unique vision. “Purpose outrides insecurity, and there is so much purpose in everything that I do,” she said.

This article is part of Office Hours, a series that connects you with entrepreneurs and expert tips for running and growing a business right now. Find their can’t-miss conversations here.