Alright – so today we’ve got the honor of introducing you to Cheryl Cox. We think you’ll enjoy our conversation, we’ve shared it below.

Cheryl, looking forward to hearing all of your stories today. What’s the backstory behind how you came up with the idea for your business?

I was a Montessori teacher for 17 years when in 2016, I was encouraged by a good friend to try an improv class at The Second City in Chicago. Even though that sounded somewhat terrifying to me, I decided to try it because I believe we grow by getting outside our comfort zones. Well, after the first class, I was hooked and went on and completed The Second City Training Center Improvisation Program. After experiencing the social and emotional benefits of improv myself, I envisioned offering improv workshops in my Montessori after-school program, as opportunities in the theater arts were nonexistent. I designed my first workshops with kids ages 9-12 years old. The first workshop was a success! Fortunately, the formula I chose regarding the age group, number of weeks in a session, class length, minimum and maximum number of kids per class, and the price worked. The students were learning how to collaborate, creatively think, refine their listening skills, and boost their confidence all while laughing and having fun. I even began incorporating improv games into my lesson plans to make learning in the classroom more fun. In the summer of 2020, parents asked if I could offer classes outdoors with masks because summer activities were shut down due to Covid. I agreed and began offering improv summer camps in my backyard ever since. I was having so much fun teaching improv workshops and witnessing the many benefits among my students, that I decided to apply some of the rules of improv to my life. I decided to “Yes, And” following my passion for teaching kids improv, risk failure, and start offering my workshops to a broader community. As a result, Woodstock Improv officially launched in 2023.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I grew up south of Chicago, and my family always valued humor and making people laugh. My early memories are of my mom taking me to a trick shop where every gag gift under the sun could be found. She bought a fake broken window, a plastic snot, a hand-buzzer, rubber poop, and the classic snake in a can of peanuts. Growing up, I would sneak episodes of Monty Python and Saturday Night Live around age eight. Gila Radner was my idol and the first vinyl I ever bought was her “Gilda Radner Live From New York”. Paradoxically, I was a shy kid, so I never participated in any theater in high school however, I loved art. I received a Bachelor of Fine Arts degree in design. Fast forward to my time living in Albany, New York while my husband was pursuing his Ph.D. I was teaching kids’ after-school outreach programs through the Albany Institute of History & Art. The family living next door to us were Montessori kids. I had never heard of the philosophy I first saw on their bumper sticker. I loved teaching art to kids, but the Montessori philosophy resonated with my beliefs about what education should be. A pedagogy encompassing a “whole child” approach that considers children’s social and emotional needs and implements hands-on learning at one’s own pace. I went on to receive my Montessori training in 1998 and was in the classroom for 24 years before resigning in 2022 to pursue my entrepreneurial dream of teaching improv to kids and teens in my community. Launching a business that combines my passions for comedy and education was a natural next step for me. My Montessori background helped me see the connection improv has to social and emotional learning. I believe in the transformative power of improvisation to enhance life skills, including the 4 Cs of 21st-century skills: Communication, Collaboration, Critical Thinking, and Creativity. Research has indicated that improv classes may positively impact children’s social skills, self-esteem, and overall well-being. My workshops and classes aim to create a space of acceptance and respect where everyone feels safe and comfortable taking chances and not fearing failure, being open and playful. I want to empower people to trust themselves and to be transformed by all the benefits of improv.

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

I was a Montessori teacher for 17 years when in 2016, I was encouraged by a good friend to try an improv class at The Second City in Chicago. Even though that sounded somewhat terrifying. I decided to try it because I believe we grow by getting outside our comfort zones. Well, after the first class, I was hooked and went on and completed The Second City Training Center Improvisation Program. After experiencing the social and emotional benefits of improv, I envisioned offering improv workshops in my Montessori after-school program, as opportunities in the theater arts were nonexistent. That was the first step in creating my side hustle: seeing a need in my community. I designed my first workshops with kids ages 9-12 years old. The first workshop was a success! Fortunately, the formula I chose regarding the age group, number of weeks in a session, class length, minimum and maximum number of kids per class, and the price worked. The students were learning how to collaborate, creatively think, refine their listening skills, and boost their confidence all while laughing and having fun. I even began incorporating improv games into my lesson plans to make learning in the classroom more fun. In the summer of 2020, parents asked if I could offer classes outdoors with masks because summer activities were shut down due to Covid. I agreed and began offering improv summer camps in my backyard ever since. I was having so much fun teaching improv workshops and witnessing the many benefits among my students, that I decided to apply some of the rules of improv to my life. I decided to “Yes, And” following my passion for teaching kids improv, risk failure, and start offering my workshops to a broader community. As a result, Woodstock Improv officially launched in 2023. My good friend who suggested I take my first improv class, passed away in December of 2022. In his memory, I created a legacy scholarship in his name and I’ve offered it to one student per class since I founded my business. It’s my way of giving back to my community.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

I think my twenty-four years of experience as a Montessori educator helped build my reputation in my market. I had already established trust with my students and families, so they were willing to try my workshops. I also think the testimonials from parents and children also strengthen my reputation in my industry and will continue to help my business grow. As a Montessori educator, I could recognize the connection between improv and social and emotional learning (SEL). With reports of anxiety and depression on the rise in tweens and teens, I believe parents are looking for unique and engaging opportunities for their children to combat such issues. “Laughing While Learning” is my tagline that implies not only are kids going to have fun in my classes, but they will learn valuable life skills, too.

Contact Info:

• Website: https://www.woodstock-improv.com/
• Instagram: https://www.instagram.com/_woodstockimprov_/
• Facebook: https://www.facebook.com/WoodstockImprov/
• Linkedin: https://www.linkedin.com/in/cheryl-cox-chicago/

Image Credits
Sara Johnson Photography Rockford, IL for professional profile picture credit