Meet Ken Gregory

We were lucky to catch up with Ken Gregory recently and have shared our conversation below.

Ken, so excited to have you with us today. So much we can chat about, but one of the questions we are most interested in is how you have managed to keep your creativity alive.

Keeping creativity alive is a challenge, especially when you’re in an industry that is experiencing a massive influx, downturn and influx. For myself, it’s been my practice to take classes to either enhance my current skill set or learn a new skill set. 2024 was extremely difficult in the entertainment industry, so much so that there was a new catch phrase, “Survive to 2025!” So I spent all of 2024 learning screenwriting. The entire year was dedicated to writing, which I’m glad I did, because we arrived into 2025, surviving to it wasn’t enough. 2025 has made 2024 look like child’s play, however for me, I wrote, directed and executive produced two new projects, while many of my colleagues either moved out of state and out of their careers in the industry.

Appreciate the insights and wisdom. Before we dig deeper and ask you about the skills that matter and more, maybe you can tell our readers about yourself?

I am a Writer, Director and Executive Producer, whereas before, circa 2023, I was an Actor and Executive Producer. I wrote, directed and executively produced the short film Becoming Sidney, which is the origin story of the late, great Sidney Poitier and how he went from being a dishwasher to an award winning actor/legend. The story is based upon the story Mr. Poitier told in countless interviews of how he got started in the industry.

I also wrote, directed and executively produced a short comedy titled Vee & Pete which is about a young couple and their undeniable chemistry, which sets off sparks, but their fear of commitment leads them down a hilariously disastrous path of experimentation with other people—each misadventure proving more chaotic than the last. As their misguided attempts at casual flings spiral out of control, their most opinionated critics—Max’s, the lead male character’s overconfident penis, Pete, and Lola’s, the lead female character’s sassy, no-nonsense vagina, Vee—offer unfiltered commentary on their every move.

Both films are making their way through the film festival circuit.

Looking back, what do you think were the three qualities, skills, or areas of knowledge that were most impactful in your journey? What advice do you have for folks who are early in their journey in terms of how they can best develop or improve on these?

The three qualities that have helped me become most impactful on my journey as a multi-hyphenated creative are Persistence, Ingenuity and Self Reliance. To be gainfully productive in the entertainment industry requires a high level of persistence! Not taking “NO” for an answer. Ingenuity means being flexible! The ability to be able to pivot on a moment’s notice is key. Knowing when something is not working in your formula and making the adjustment needed in order to shift so that productivity isn’t affected and efficiency is maintained, will be beneficial in this business. Self reliance, means having multiple choices, options and sources that will keep you and your projects from being derailed. There’s an old adage that I learned years ago growing up in Detroit, “NEVER put all of your eggs in one basket!” Diversification is the key to successfully avoiding stagnation.

What’s been one of your main areas of growth this year?

I pointed out earlier about how I spent all of 2024 learning screenwriting and by doing so I was able to “create” growth in my career. Learning this essential skill helped me to understand how to develop story and understanding storytelling structure. By doing so, it pushed me to create strong characters in unique environments… meaning… knowing how to build worlds that people would want to know more about and be willing to take a ride on the journey that I created through powerful storytelling.

Contact Info:

Image Credits

Personal Photo – Leah Huebner of Huebner Headshots

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