Today we’d like to introduce you to Chester Gregory.
Hi Chester, thanks for joining us today. We’d love for you to start by introducing yourself.
I’m from Gary, Indiana, a city that gave me both grit and dreams. Music was my first language, and I grew up singing, performing, and imagining crowds cheering me on. That passion led me to my first big break in The Jackie Wilson Storywhich, in the same week, put me face to face with Michael Jackson and landed me on Broadway.
Broadway became home for over a decade. I created roles in Hairspray, Dreamgirls, Shrek, Tarzan, Sister Act, Cry Baby,and Motown the Musical. Playing Berry Gordy and later meeting him was a full circle moment that reminded me how powerful storytelling can be when it is lived fully and shared honestly.
Today, I’ve expanded from Broadway to music, wellness, and coaching. I built THE C.H.E.S.S. BOARD [Collectively Healing Every Single Soul], a community that uses performance, creativity, and wellness practices to help people align with their higher purpose. For me, the lesson is that no matter where you start, the dream inside you can outgrow the limits of your environment when you keep showing up and believing in it.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
Not at all. From the outside, it looked like success was stacking up. Behind the scenes, had a failed marriage,I lost my father to suicide and I numbed myself with unhealthy coping mechanisms. Even while starring on Broadway, I battled self doubt and imposter syndrome.
The lowest point was when I lost my voice. Along with it, my career, my passion, and my way of providing for my family felt like they were slipping away. That moment forced me to stop running, face the darkness, and rebuild from the inside out.
That healing journey gave me tools I now teach to others. I learned that the same places where you feel broken can become the places where you discover your deepest resilience. Pain can strip you down, but it can also rebuild you into someone more grounded, more present, and more alive to your own purpose.
As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
I live at the intersection of art, performance, and transformation. Broadway gave me the gift of discipline, authenticity, and emotional connection. Now, I use those same tools in my coaching and wellness work to help people find their voice, overcome self doubt, and align with their purpose.
I’m proud of the communities I’ve built. Through music, shows, and THE C.H.E.S.S. BOARD, I’ve created spaces where people don’t just watch a performance, they experience something that shifts their perspective.
What I am most proud of is that my journey has come full circle. The same lessons I learned on stage such as discipline, authenticity, presence, and emotional connection are the same principles I now share with others to help them step into their power. What sets me apart is my ability to merge artistry with personal development. I use performance not as entertainment but as a tool for healing and transformation.
We’d love to hear about how you think about risk taking?
I see risk as the price of growth. Every breakthrough in my life has come from stepping into the unknown and trusting that the ground would appear beneath my feet.
Pursuing the arts was a massive risk. I could have chosen a safer path, but I chased the dream, and that choice led me to Broadway, to music, and to sharing stages with my heroes.
Later, the riskiest move was telling my truth. Opening up about loss, imposter syndrome, and pain felt vulnerable, but that choice built real connections and gave others permission to embrace their own humanity.
Risk is not about recklessness. It is about listening to your inner voice and moving forward even when you cannot see the full picture. The lesson is that comfort never grows you, and uncertainty often carries the key to becoming who you are meant to be.
Contact Info:
- Website: https://www.chestergregory.com/
- Instagram: http://instagram.com/chestergregory
- Facebook: https://facebook.com/chestergregory
- Twitter: https://x.com/chestergregory
- Youtube: https://www.youtube.com/@OFFICIALCHESS
- Soundcloud: https://soundcloud.com/chestergregory
- Other: https://open.spotify.com/artist/2Bilj0SkDO40wCxtBhs7t8
