We caught up with the brilliant and insightful Jessica Leving Siegel a few weeks ago and have shared our conversation below.

Alright, Jessica thanks for taking the time to share your stories and insights with us today. What’s one of the most important lessons you learned in school?

In fifth grade, I had the opportunity to participate in a program called ThinkQuest, Jr. that challenged teams of students to create websites on educational topics.

My brother, Billy, had been diagnosed with autism a few years prior, and I had hated watching him struggle among peers who just didn’t get it. The website project seemed like a great opportunity to do something that might help.

I suggested creating a website focused on explaining autism and other disabilities in words that young children could understand, through interesting stories about real people. My team agreed–and soon, my very first website was born.

We ended up winning an award, and with the award came the opportunity to share our website in classrooms locally and nationally. (We even presented to out-of-state classrooms virtually, all of us gathered together at the library in front of a projector screen, webcam, and a dial-up internet connection –a 1990s version of a Zoom call!)

Amazingly, things really did change for Billy after the website started gaining traction. I got to share the website with his class, and his peers began learning to ask thoughtful questions instead of making assumptions. Slowly, they started including Billy, instead of leaving him out when they didn’t understand his behavior. Because of that basic little website, Billy’s whole world changed.

The experience changed my world, too. I had always loved writing and photography—but this time it was different. This time, I had told a story that mattered. I really believe that the thrill and satisfaction I got from that experience is what set me down the path to study journalism and marketing, work for nonprofit communications departments, and eventually, start my own company.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I am the founder and CEO of Sing Creative Group, a small but mighty marketing and creative services agency headquartered in Chicago, Ill. We specialize in helping clients in the social good sector harness the power of storytelling to hone their messaging and amplify their impact.

Before launching Sing Creative Group, I initially got my start as a journalist, writing for publications such as USA Today, The Boston Globe, The Jerusalem Post and more. When I realized I wanted to use my storytelling skills to champion the causes I cared most about, I moved into the nonprofit world, and spent 10 years working on internal comms teams for organizations such as The Jewish United Fund, Spertus Institute, The American Lung Association, and Walder Group.

Now, at Sing Creative Group, I’m able to leverage my experience and expertise to help other changemakers hone their messaging and amplify their impact. Recent PR wins for our clients have included hits in Parade, HuffPost, USA Today, The Chicago Tribune, ABC7 News, and more.

Outside of my company, I am also the author of three children’s books, host of The Special Siblings Podcast, and the founder of my own nonprofit organization, The Center for Siblings of People with Disabilities. My experience running a nonprofit is invaluable when serving nonprofit clients and working with boards!

Education-wise, I earned my MBA from The Kelley School of Business at Indiana University, and I also hold a BS in Journalism from Boston University, in addition to several smaller certifications and training programs.

Can you talk to us about how your side-hustle turned into something more.

I really fell into this work as a “side-hustle” without intending to, at first. I was working in the communications department of a large nonprofit, and had volunteered to help with newsletters and media outreach for a few other organizations I cared about on the side. My network got bigger and bigger, and eventually someone passed my name along to an organization looking for one-off comms help with a special project. I said sure, why not?

Well, one thing led to another, and eventually I was making nearly as much from my side projects as I was from my main gig. It got to the point where I was needing to turn down clients because I didn’t have time to balance everything. Finally, I took the risk and jumped ship from my 9-5 to focus on freelancing full-time.

As soon as I freed up my schedule by quitting, more clients arrived to fill the gap. Things were chugging along fine and I was enjoying working on various projects as they came in, until I realized I needed to start thinking like a business owner if I ever wanted to scale up. I started partnering with specialists in areas where I wasn’t as deeply experienced–like graphic designers and tech folks–and soon I was able to move into more of a “Creative Director” role.

Now, I love being the one to set the overall strategy and empower others to help me bring a vision to life. Plus, I get to have my hand in double the number of projects and causes as before, which I enjoy!

Do you have any insights you can share related to maintaining high team morale?

I’m still learning how to be a better manager every day — but everything I do is based on the premise of hiring kind, talented people that I feel I can trust to do a good job without micromanagement once I’ve shown them the ropes.

I recently went on maternity leave and left my team in charge of basically my entire company while I was out. It was terrifying to give that much power over to others, and trust them with something I had built from the ground up. But I knew it was either that or be forced to pause all my contracts (and thus, have no income — plus potentially lose clients for good) until I was ready to come back to work.

I took the risk, and when I came back all my clients were still as happy as ever! That experience gave me a huge boost of confidence in my team, and solidified my belief that if you don’t trust the people who work for you to deliver even when you’re not right there breathing down their neck… then they shouldn’t be working for you.

Contact Info:

• Website: www.singcreativegroup.com
• Instagram: https://www.instagram.com/singcreativegroup
• Facebook: https://www.facebook.com/singcreativegroup
• Linkedin: https://www.linkedin.com/company/singcreativegroup

Image Credits
Photos courtesy of Jessica Leving Siegel.