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Conversations with Chester Gregory

Today we’d like to introduce you to Chester Gregory.

Hi Chester, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
Also known as C.H.E.S.S. I am an artist of serval disciplines and I’m originally from Gary, Indiana – the home of Michael Jackson- and that is part of what sparked me to pursue a career in the arts. Every day on this earth is a blessing, and I plan to use my gifts to inspire as many people as possible. I have performed all over the world, including Broadway and I’ve worked extensively in the studio recording and releasing music. Whether it’s acting, singing, writing, producing, or consulting, I love art! I’ve collaborated with many artists in the industry. Most recently, have enjoyed being a content creator, making an exciting transition into television and film.

Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
Though I strive to live each day in gratitude, I have faced depression and crippling self-doubt for several years. Recently, I have done an immense amount of inner work to overcome those obstacles. I am now much more grounded and transparent with my journey. Knowing that I’m contributing something that makes a positive difference in the world brings me joy.

Appreciate you sharing that. What else should we know about what you do?
I am viewed as multifaceted. In addition to being an actor, singer, recording artist, and performer, I am a content creator, a black-owned business offering coaching services, consultations, merchandise -and am currently working on my latest album called “Retrograde.” All of those things are components of who I am, genuinely, and to be able to both do work that I love and give back, means so much to me.

Where do you see things going in the next 5-10 years?
There is no way to predict how this industry will evolve, and I am not concerned. The past 18 months have taught us that how we experience art may change, and even though it looks totally different from how we may have imagined, it is still alive, still viable.

As an artist, we need to adapt and grow with the times, with the goal of remaining authentic. For me, that means to be true to how my convictions speak to me, to reflect the times even as they change, and to do my part in adding value to the world. No matter how it changes, we must keep moving forward.

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Image Credits:

Jonathan Adjahoe

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