About Jessica Zweig



  1. to go, move, or journey from one place to another
  2. to go, move, or cover a specified or unspecified distance
  3. to withstand a journey
  4. to progress or advance

We all know what we think of when we hear the word travel: suitcases, security lines, planes, trains and every type of automobile. However, my definition of traveling has less to do with airplanes and more to do with that epic adventure also known as your life.

Over the past two years, I’ve been to 20 international cities, which have shaped how I see the world and how I approach business.

But I also believe we “travel” in everyday ways: from job to job, opportunity to opportunity, meeting to meeting, relationship to relationship, revelation to revelation and even emotion to emotion.

We travel through daily life

So here, you’ll find travel guides, interviews and life lessons with badass boss babes, an in-depth look at the evolution of social media and how it has the power to connect strangers worldwide (I’m looking at you, Snapchat) and how we can explore our world through our passions.

At its core? It’s a place for authenticity, clarity, inspiration and adventure. It’s a place to SimplyBe.

Because we all have our own roads. This one just happens to be mine.

Welcome to the RoadJessTraveled.

On a more “professional” note…

Jessica Zweig is one of Chicago’s most recognized women entrepreneurs, known for creating businesses, audiences and conversations. She was named one of the Top 7 Digital Marketers to watch in 2017 by INC.

In 2008, she founded Chicago’s largest digital lifestyle magazine for women, CheekyChicago.com, publishing over 100 monthly articles, reaching over 100,000 local millennial women and capturing some of the most prolific global brands as clients.

Jessica’s work as an entrepreneur catapulted her into the consulting world, when she partnered with Starcom’s global digital agency, Liquid Thread, launching Skinnygirl Cocktail’s new product line and growing its social community to over 1 million followers.  In 2014, The SimplyBe Agency was born; bringing her expertise in brand positioning, content marketing, digital and experiential strategic vision to her clients, ranging from venture-backed start-ups to Fortune 500s.  The SimplyBe Agency utilizes Snapchat / V3 marketing and strategy as its core pillar of consulting services.

Jessica has spent the recent part of her consulting career working for lifestyle brand, DreamTrips, designing, launching and scaling its hyper-local innovation product in over 25 markets across the world for a 500,000 customer base.  

Jessica has been featured in CrainsChicago TribuneChicago Suntimes, Refinery 29, Tasty Trade, BizTech MagazineToday’s Chicago Woman and Michigan Avenue as a leading entrepreneur. She’s spoken at Techweek Chicago, The United Women in Business Foundation, Independent Awakening’s Fireside Chat series and more as an expert on marketing and branding. She’s also a mentor at the Founder’s Institute, the world’s largest entrepreneur training & start-up launch program, powered by Microsoft.