Cheeky to Simply

As part of living in Chicago, I've had the privilege of associating myself with intellectuals and social enthusiasts from various backgrounds who have opened my eyes to a different side of the world. One of my favorite activities here was being a part of Cheeky Chicago, a social group for the cosmopolitan woman. This was founded by the city's very own socialite, Jessica Zweig, who has been making major strides in the entrepreneurial space. As she moved onto her new chapter, The SimplyBe Agency allowed her to flourish into something more powerful than she ever imagined. Fortunately, I had the opportunity to grab some of her time, and get a peek into her world. 

On Entrepreneurship

Q: As an experienced entrepreneur, what are the 3 top underrated skills a woman must work towards?

JZ: Creating work-life balance. Learning to say no to the bright shiny objects. And being highly selective and overly cautious with whom you partner/go into business with. 

Q: Everyone raves about your aptitude to deliver quality work. What is your secret?

JZ: I believe anyone can be taught any skill, but you can’t teach ambition. You’re either born with it or not. I thrive in hard work. I love to execute and deliver. It makes me feel alive and empowered. I translate that drive into the work I do for my clients and audience. It just comes naturally to me.

Q: Is there a turning point when you know not to give up on a dream? If so, how do you know?

JZ: I wouldn’t call it a turning point, as much as an immediate knowing. There have been a few times in my life where I was able to articulate a “dream” or vision into an actual plan or concrete course of action. When that happened, it was like a divine spark. All the circuits in my mind, heart and soul lit up at once. It was in those moments I knew there was no turning back.

Q: What are some reading/watching materials you would recommend for young entrepreneurs to learn more about building a brand?

JZ: I read the Broadsheet religiously, It’s a daily newsletter sponsored by Forbes about women in business, media, politics, philanthropy and entrepreneurship across the globe. Super inspiring. I keep my business chops sharp by catching any content I can from James Wedmore (Youtube and marketing expert), Natalie MacNeil, Amy Porterfield and Hilary Rushford. I also follow Danielle LaPorte for inspiration, perspective and insight on all things feminine and entrepreneurial. Those are for sure my go-to’s. 

On The SimplyBe Agency

Q: If you had unlimited resources, what would you do differently for The SimplyBe Agency?

JZ: I would probably launch my “SimplyBe TV” YouTube show full-time and fly around the world to interview all the great entrepreneurial, creative and powerful women who inspire me and so many: Oprah, Elizabeth Gilbert, Hilary Clinton, Jessica Alba, Amy Poehler, Laurie Greneir… The list goes on and on. I would dedicate my show to telling their stories in a totally new light.

Q: In a quickly evolving world, how do you keep your content fresh and captivating?

JZ: Honestly, I just strive to be authentic. I think being yourself is always in style and people are drawn to truth and vulnerability in any form. Plus, I really don’t spend any time “keeping up with the Jones’s.” If anything, I love seeing other talented babes (and bros) evolving in their own right – growing their fan bases, launching new products, creating cool collaborations – it inspires me to simply to keep ‘doing me.’ That’s the most critical aspect in evolving – staying true to who you are and never comprising that to achieve a projected notion of success. You are the only one able and responsible for defining that for yourself. 

Q: Among the coaching, agency, and speaking programs, which one is your personal favorite? Which one would you recommend for beginners?

JZ: I have had to limit aspects of my business as I work full-time for a corporate company right now, but I really love my coaching practice. I work with a very short, select list of clients who I absolutely love. We have mutually invested so much time and work into their companies and I have really been able to see the fruits of our labor come to fruition. There’s nothing more gratifying than seeing my clients grow and succeed. Plus, the personal connection and deep friendships that have occurred as a result of our time together just makes it all that much sweeter. 

Q: What do you hope to tackle and conquer in the years to come for SimplyBe? 

JZ: I have a handful of things in the mix, which I can’t really talk about, but let’s just say the future involves creating new platforms for communities of empowered women to support each other in various capacities around various topics. The brand will be evolving into less of what Jessica Zweig has to say and more about what you have to say. I’m super excited about it. 

On Personal Matters

Q: How do you keep yourself energized and motivated? And so gorgeous? ;)

JZ: First of all – thank you. That’s very sweet. Over the past few years, I’ve definitely learned the importance of balance. There has to be a yin to the yang of hustle. This requires a dedication to space and time to check out and take care of me. I swear by Transcendental Meditation, lots of sleep, lots of water, green juice, supplements, Pilates and regular facials by Leah Chavie. Spending time with my husband and my dog Zooey is the most nourishing and grounding aspect to my life. My little family is everything to me and I ensure I am always making time to prioritize what really matters. Happiness makes you glow from the inside out and I have to say, I’ve never been happier. 

Q: Did your childhood pave the way to your entrepreneurial stature?

JZ: You could say that it did. I have incredible parents, who are both fiercely hardworking and entrepreneurial in their own right. Plus, they have always let me “be me” and have supported all my endeavors. I’m very lucky in that way.

Q: Whom do you look up to? How frequently do you have 1-on-1 coaching for yourself?

JZ: I look up to any woman who is brave enough to take risks, transcend her fear, go for her dreams and put herself out there with authenticity, humor and irreverence. I do indeed work with a business/life coach – her name is Kirsten Dais. She’s changing my game and I am so grateful to her every single day.  

Q: Which celebrity or public figure would you love to have coffee with and why?

JZ: I would say my favorite celebrity of all time is Gwen Stefani. I fell in love with her when I was 14, when she came out with “I’m Just a Girl”, when I was in the throes of my rebel days. (I really do consider myself a rebel heart, forever and always.) She is just so authentic, timeless and fierce. I love how she’s never “reinvented” herself: she’s just continued to evolve into a wiser, refined, more badass version of herself. I love her music, her fashion, her femininity, her stories and kindness. She seems to have a super big heart, and because of that, you’re always rooting for her. She’s also a trailblazer on so many levels: a female lead singer in a predominantly male musical genre; a hugely successful solo-artist who continually returns to her original band with huge success; she was one of the very first musical artists to segue into the fashion world to create her own line AND…she’s a mom to three boys who’s been through some shit and isn’t afraid to talk about it. She’s not just an artist, she’s an inspiration.  She’s not just an entrepreneur, she’s a mogul. She will always be my #1.

Throwback to 2012 during an annual Cheeky event

Hope this was as inspiring to you as it was to me!