SDH 178: Stepping into your Power and Living your Truth with Jessica Zweig

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How does your business evolve with you? Have you outgrown it? Is it time to start another one with a different direction, so it aligns with who you are today?

These were the tough questions Jessica Zweig, founder of the SimplyBe Agency, was faced with when she decided to end her first business, Cheeky Chicago, that had been running for 7 years. Launching in 2008, Cheeky Chicago was an online lifestyle magazine for women, and was of Chicago's first online destinations for the hottest socialite venues. It soon evolved to include content about dating, fashion, restaurants, buying your first home, and more.
At Cheeky's peak, they had 100,000 readers, and had sponsorships and partnerships with brands like Nike, BMW, and Bloomingdale's to name a few. Jessica gained a lot of these high-profile brand connections through Cheeky events, which she used to promote other female entrepreneurs and create strong networks among them. Cheeky events became the most buzzed about events in town and were a lucrative revenue for her brand.

With this soar in popularity, Jessica also became one of Chicago's first social media socialites. This was due to Cheeky's loud presence online, and her extensive use of social media advertising and marketing in the early social media era.

She fully basked in the limelight of being Chicago's 'It' Girl, and loved the accolades that Cheeky was racking up. But her fast lifestyle and constant work schedule began to catch up with her, and she became physically and mentally exhausted.

In 2013, she began to get chronic sinus infections, and had nine of them within the span of six months. After visiting multiple allergists, acupuncturists, and EMTs, it was determined that she needed to have surgery. She was immobilized during the month of her recovery, and with her separation from work, she entered into a deep emotional breakdown.

When she had enough of her dormant life, she went to a park by her house to meditate. However, she was overtaken by emotion and found herself crying because she had lost herself in her business and couldn't find her purpose without it. It was then when she glanced down at her wrist and saw the tattoo she had gotten years before. It read: 'Simply Be, Girls Can See it'. At that moment, the meaning struck her in a whole new light, and she whispered, 'I don't want to do this anymore.'

Cheeky Girl was no longer her source of happiness, and as she had gotten older, it was no longer who she was. On that grassy knoll, she knew she needed to walk away, and start fresh. She didn't know what her next venture would be, but she knew it was going to be titled: Simply Be.

It took Jessica a year and a half, and increased visits to her therapist, to shut down Cheeky Chicago for good; and in October 2014, the SimplyBe Agency was launched. SimplyBe Agency helps clients establish a powerful presence online by defining their personal brand, and setting them up on multiple and effective platforms to get their message out to the world.

Jessica firmly believes that in order to build a successful business and empire, you first have to build your personal brand. As she said, "People fall in love with people," and SimplyBe aims to tell their client's story in a way that touches audiences on an emotional and moral level. This creates valuable equity behind their client's name that will have a lasting effect on their audiences and business partners, and will guarantee the growth and profitability of any business venture they have down the line.

Listen in to hear more about Jessica's career evolution!

In this episode you will...

  • Find out how to use innovative resources to promote your business
  • Learn how to cultivate audiences with a 360 branding approach
  • Prioritize your mental and physical health over your job
  • Figure out how to develop a strong personal brand along with your product
  • Begin to follow your own agenda
  • Put a price point to your value and worth


"I'm going to move on eventually...I don't know what it's going to be...but it will be called Simply Be, because it is a metaphor for being authentic and for being in alignment with who you really are today, and what you really want, and what makes you feel like yourself." -Jessica Zweig

"My biggest accomplishment was following my heart, and reinventing myself, and starting from intuition was screaming at me...I heard a voice say...'You need to be still and stop, and listen to what makes you happy." -Jessica Zweig

"I just love the hustle. I love being my own boss and running my own business. When you put [everything into it], you get it out. You see your own results, and there's no better feeling than that." -Jessica Zweig

"The world needs more humanity and more people stepping into their power, and telling their stories, and being thought leaders on what they know to better service the world." -Jessica Zweig

"I strive to be vulnerable in my life...The world will be set free by people who are free...When you get honest and open, you give other people the permission to do the same for themselves...If we talk about it, that to me is the secret sauce." -Jessica Zweig


Jessica Zweig LinkedIn
The SimplyBe Agency Website
The SimplyBe Agency Blog
The SimplyBe Agency Facebook
The SimplyBe Agency Instagram
The SimplyBe Agency Twitter
RoadJess Traveled Blog
A New Earth by Eckhart Tolle

Amanda Boleyn