How She Crafted a Career Where Passion and Profit Intersect

Jenna Kutcher 

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August 24, 2020


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Educator, advocate, activist, storyteller, consultant, philanthropist, dog mom… Just a few titles that my friend Jess Weiner can hang her hat on. What Jess does is so important — She advises and leads massive brands on how to better reflect people and their diverse experiences within their media, marketing, advertising, and workforce.

She is a brilliant branding mind with a special super power of connecting companies with their communities. Jess is also expanding her work to connect with her own community and help people define what a “good life” means to them. I am so thrilled that she’s here on the podcast to dig into consulting, personal branding, marketing and messaging, building community, and more.

Who is Jess?

“I have never worked for anybody,” Jess started. She’s been living the entrepreneurial life for over 25 years. Jess earned degrees in theater, women’s studies, and classics… Areas that she joked were guaranteed not to make her any money. They gave her a foundation in areas she was passionate about, but she wasn’t sure yet how to combine them into a career.

Her very first business was a non-profit theater organization that performed social justice plays for kids, which she later sold to a university. That catapulted her to California, where she set her sights on opportunities to create and launch larger media projects and platforms to reach young audiences.

From TV projects to writing assignments, Jess learned about the industry through first-hand experience in many different areas. The partnership that opened her career doors was with the Dove Real Beauty campaign, now her longest running partnership. The Dove campaign combined all the things she loved, and it put her on the radar of other large companies who wanted to better represent people and needed education and strategy to do so.

“My career has had all of these twists and turns,” Jess shared, “But it’s been a wild ride all really built on passion and in search of profitability — figuring out how to make money doing what you love.”

Uncovering Her Superpower

Jess holds an incredible skill for translating social and cultural topics for big companies. When did she realize that was her superpower? For Jess, it all goes back to the early days of performing social justice plays for kids in her first entrepreneurial endeavor.

“I honed my skills through conversations in classrooms, dorm rooms, boardrooms, with people from all different walks of life, all different experiences,” Jess explained.

And those conversations were all about listening, she said, “That’s where I honed my expertise to listen. I listened between the lines and I listened with an open mind. I allowed myself to be challenged in ways that were deeply uncomfortable but necessary in order to connect to a broader audience.”

Instead of leaning on statistics and studies to learn about people, she actually listened to and learned from the multi-faceted humans themselves. And she lends those skills to large companies who don’t have the time to hone those kinds of skills for themselves.

And when it comes to fielding requests for her services, Jess uses those listening skills to figure out why the company really wants to develop a specific campaign. If she can’t get a read on the true motivations behind launching, for example, a women’s empowerment campaign, she might determine that the company doesn’t have an authentic drive to do good, and therefore, could cause inadvertent harm to their audience. This is all part of Jess’ superpower.

Poised to Pivot

Jess and I talked about all of the incredible work she’s done alongside major brands like Dove, Mattel and Barbie, Aerie, just to name a few. And now, Jess is poised and ready to pivot into the side of herself that she says is always “seeking”.

“I’m closer to 50 than I am 40, and I’m feeling the urgency of time,” Jess explained. With over 25 years of hustling, she’s exhausted and yearning for more of the creative expression that she had at the start of her career.

“And for a minute, it’s been a little bit scary because clearly, why would you want to rock a boat that’s sailing pretty smoothly?” But she continued to explain that she’s choosing not to view it as rocking the boat any longer. It’s more about expanding and asking “why” for herself.

Jess candidly shared that she’s had many experiences of watching those close to hear pass away before they could realize all of the experiences they wanted to have while alive. “That has left an indelible mark on me. We know time is not promised, but it’s really embedded in my right now,” she explained.

Inspiration for her Podcast

Part of Jess’ pivot is her connecting with her own community and helping people (as well as herself) define what it means to live “a good life”.

Jess shared a story about one of her clients, a woman who had been given just two months to live after a stage-four cancer diagnosis. During one conversation, the woman shared with Jess the things that she was thinking about as she approached the premature end of her life.

One of those things was that she felt she spent too much time and gave too much weight to toxic people who didn’t care about her. And the other thing she told Jess was something that has stayed with Jess the most. She said she did all the right things, hit all the career milestones, achieved all the things she thought she was supposed to achieve, but didn’t spend enough time learning about herself.

Jess recognized that she had spent so much of her life in the hustle, focusing on the to dos, and not fully knowing or understanding herself. That conversation was the inspiration for hosting conversations about what makes a good life on her podcast “We’re All Going to Die Anyway”.

More from this Episode

We dig into how she’s navigating conversations about living a good life before death on her podcast, why she’s giving herself permission to be a student again, and are wisdom and confidence earned with age or can they be acquired in other ways? Hit play on the episode above to hear all of the magic that Jess Weiner brings to the show. Be sure to connect with her at @imjessweiner on Instagram.

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Before you get any further... Hi! I'm Jenna Kutcher!

A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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