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Life & Work with Cindy-Ann Boisson of Miami / South Florida

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

Hi Cindy-Ann, we’d love for you to start by introducing yourself.
What was initially a move to support my son’s swim scholarship dream turned into me chasing my own dreams onto the stage. Keegan was a national swimmer and believed he had what it would take to earn himself a swim scholarship so, in 2010 we moved to Florida. Once he was off to college, I finally had some time to, firstly, rearrange the ‘nest’, then to follow my dreams of becoming a standup comedian/actor.

Losing my dad in 2014 shattered my world; I didn’t think I would ever get back on stage. In 2015 I got booked for an event after not performing comedy for about a year and well, I’ve been on stage since.

As the years passed on, I have come to realize that in order for me to evolve and truly ‘live my truth’ (that phrase is so abused lol), I had to let go of some of my cultural norms I was a prisoner too. Letting go of shame and fear of judgement. Not caring what people think or say. They don’ t know me! Right? Exactly. In full transparency, I did and continue to do a lot of therapy! A lot! Learning who I am and loving on me. Darling, I wish that for everyone. Forgiving others and more importantly forgiving myself! Honey! No greater love exist.

I am where I am because I worked at it and continue to work at and have always had a wonderful village to support and love on me.

I write. A lot. I read (audible still counts, right?) a lot. I am very intuitive and observant. I know my worth.

The journey continues.

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?
Smooth road? Is that even a thing. If the road was smooth I would be skeptical! It’s been bumby and winding, you hear me? Potholes, sinkholes…speed bumps. You name it. But…I am an excellent driver. I’ve learned when to switch up the routes. Read the signs. Keep a keen eye on those other drivers. Maintain this ‘vehicle’!

As a black, Caribbean, female immigrant sometimes it can all feel like a struggle. I was told I needed to change my accent to get ahead in this business. Boooooo! Thankfully, the support I received drowned out that perspective.

I am older. I got into comedy in my late 30s and this business is a hustle. Trying to keep up can sometimes feel like a struggle. Not a physical struggle just trying to understand these youths because what are they even saying at times? LOLOL. Keeping up with pop culture. It’s a struggle to keep up with everything that’s going on.

This business can be brutal. Finding and nurturing relationships that nourish you that you can also pour into took some effort: I’m in a good place now.

Social media is another thing I am learning to navigate. In my days (here I go sounding like the old aunt at the holiday party lololol) we didn’t have all this algorithm stuff to contend with. Your life was your algorithm. What to post. When should I post it. Do I have the right equipment. I am always driving alongside Struggle Ave… I wouldn’t trade it for the world though. The truth is, it’s a struggle I love. A good kinda struggle. I am learning. I am growing. I am thriving.

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 am a standup comedian, storyteller and actor.

I’d like to think I am known for my ability to make people laugh and sometimes look at things differently and even forget their own pain at times.

In 2024 I produced and performed my very first One Woman Show called God’s Favorite. It was a blend of sizzling humor and poignant storytelling sharing my experiences migrating to the United States, navigating motherhood, grief, and discovering my passions. That is one thing I am most proud of.

My resilience! Gosh! So damn proud of my bounce back game each and every time.

I am proud of my work as a volunteer. I have been a Literacy Ambassador with Hands on Broward, reading with elementary school children, for +10yrs and have worked with Mental Health South Florida by going into elementary schools and enlightening children about the importance of respect and responsibility. I am proud of that! I love working with kids. Those volunteer hours actually birthed Tickled – A Children’s Comedy Workshop I produce.

I truly believe what sets me apart from others is my vulnerability. I am very comfortable with the uncomfortable. Having an earthly father that mirrored what I imagine my heavenly father to be has been my super power. He taught me to trust my gut and intuition and to look people in their eyes! It took me a long time (too long) to realize that most people are sometimes so drenched in their own shame that they are very uncomfortable with how comfortable you are with acknowledging and accepting your own. I mean, how else am I suppose to heal?

Any big plans?
I plan on keeping on keeping on! I want a comedy special. I want to be a global name. I want my stories to resonate across cultures.

As for my big plans/changes? You’ll have to see them unfold in real time (I am a little superstitious, you know. I don’t want to jinx it. Ha!)

Contact Info:

Woman reading a book to children in a classroom, colorful educational posters on the wall.

Woman with curly hair in white top and black sequined skirt at fashion event, holding a phone, standing in front of a blue backdrop.

Young woman with a ponytail smiling, holding a microphone on stage, wearing a white shirt and purple tie.

Woman with curly hair wearing a black sequined blazer and smiling, standing against a dark background.

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