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Conversations with Cindy-Ann Boisson

Today, we’d like to introduce you to Cindy-Ann Boisson.

Cindy-Ann Boisson

Hi Cindy, please kick things off for us with an introduction to yourself and your story.
I performed comedy for the first time at the Hollywood Improv in Fort Lauderdale on June 28, 2014. My son was off to college, and I needed to find my thing!

Standup comedy turned out to be exactly that. Since then I’ve done hundreds (maybe thousands) of open mics and shows across the country. When I first started I hated open mics but it’s critical to your success as a comedian. I mean, if you’re fortunate enough to be booked regularly then you get to workshop your jokes that way. There are no shortcuts, you have to workshop those jokes.

I would say persistency, determination, resilience and passion (also tears, prayers and some cuss words helped fueled me) got me to this point. In 2016, I created my own brand with the help of some friends and that allowed me to grow a supportive fan base in Florida and Trinidad and Tobago.

At the beginning I never said no to. Anything. I wanted to perform so any opportunity was a good opportunity. Today, I’m more selective. I mean, hey! I’ve earned it. Right?!?!?

Networking! Boy did I network and continue to do so. Although it may appear to be otherwise standup comedy is a team sport! Being able to find your tribe is so important and also such a challenge. I feel like I’m finally finding what feels like home to me.

We all face challenges, but would you describe it as a relatively smooth road?
Has it been smooth? Road? Absolutely not! I’m a black (Red woman. It’s an inside joke. Iykyk).

Trinidadian woman existing in a male/white male/white female industry. The pathway for someone who looks and sounds like me is paved with struggles! I always feel like I need to work ten times as hard to prove myself. To the best of my knowledge, I’m the only native Trinidadian doing this sport in the U.S.

It’s a blessing and a curse. I wasted a lot of time searching for representation. Trying to find someone who worked the struggle pathway to give me some clues on how to navigate the course. Then it hit me! I’m the representation bish!

Once that realization hit me my outlook changed. I was like okay… I’m ready for these streets! It’s exhausting at times and I’m still figuring ways to replenish but boy am I ever so ready.

Knowing my worth and what works in my best interest is something I’m always negotiating. These are difficult conversations to have to with myself and anyone else. It has gotten easier for me to say no and when I say it I get tis warm and fuzzy feeling like… yes girl! Yesss!!! Let them heauxs know you’re worthy.

Can you talk to us about happiness and what makes you happy?
What makes me happy and why? Deep conversations and laughter with my loved ones make me happy. I think that’s self-explanatory, right? I love them.

Quiet moments with myself make me happy. The older I get, the more I realize how important it is to spend quality time with and by myself. I’m my best friend.

Shopping! Retail therapy brings me joy! Until it’s time to pay my credit card, I’m really sad. It’s a vicious cycle! My son makes me happy. Ah, love him. Just spending time with him fills my cup.

Prayer brings me joy. The ability to say what’s on my mind! Ooooh boy, Joy! Joy! Joy.

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Image Credits

Ricardo Reyes and Steve Filmrunner

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