An Inspired Chat with Cindy-Ann Boisson of Fort Lauderdale, Broward County

We’re looking forward to introducing you to Cindy-Ann Boisson. Check out our conversation below.

Cindy-Ann , so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What do the first 90 minutes of your day look like?
Hmmmm…what do the first 90 minutes of my day look like? I try not to look at social media as soon as I open my eyes. I log on to youtube and say my morning prayers THEN I jump feet first into the social media rabbit hole. I’m usually quite good and cutting it off and going out for my walk. I LOVE taking long walks first thing in the morning; It clears my head. Once I am on the move a good audiobook keeps my company or sometimes I listen to a podcast that help my creative juices flow or spend some time on the phone with one of friends.

Honestly, starting my day with a 90-120 min walk not only benefits me….It benefits everyone around me. You know what I mean? lolol

Can you briefly introduce yourself and share what makes you or your brand unique?
Hi! I am Cindy-Ann Boisson, standup comedian, storyteller, actor and professional mischief maker! I was born and raised in Trinidad and Tobago and migrated to Florida in 2010. The move was to see my son through high school and support his dream of earning a swim scholarship. I never intended to stay in Florida. The loss of my dad in 2014 rocked my world and and altered the course of my life.

My journey in comedy started in 2014 after completing a standup comedy workshop at the improv in Fort Lauderdale Florida. Once I lost my dad I took about a year off and dove head first right back into it.

When I started I spent a lot time search for representation; I was searching for a sense of belonging. I’ve been comedy for just over 10yrs and have never met or heard of another native Trinidadian performing on the bigger stages in the United States so for a long time I struggled to see myself in this role; there was no representation. It took awhile for me to come to the realization that perhaps I am the representation. Hopefully others looking on can see themselves in me and feel inspired.

Migrating as an adult came with so many challenges. It forced me to rediscover who I was and who I could become in a completely new environment. New rules. Different culture. Strange community. Getting into comedy was my coming home moment. The stage became my home. It is where I feel most present.

I believe what makes me special is my ability to take my experiences and weave together a compelling story that takes the audience on a journey. In 2024 I wrote, produced and performed my first One Woman Show entitled God’s Favourite and I remember experiencing the sounds of laughter and tears from the live audience. I knew I was doing something right; it showed the powerful impact I was having.

I am a black Caribbean woman. An immigrant. A mother. A wife. A friend. I am a comedian. A storyteller. An actor.

I have ADHD, OCD and HGTV.

I am currently touring her bold, unfiltered, and deeply relatable stand-up comedy show, The Red Woman Tour. The Tour is a fearless celebration of Caribbean identity, womanhood, and the art of keeping it real — all delivered with sass, smarts, and unforgettable punchlines.

Great, so let’s dive into your journey a bit more. What relationship most shaped how you see yourself?
What relationship shaped how I see myself? My relationship with my parents. God! My dad and I shared such an unbreakable bond. He told me I was the ten the most important people in my life. He taught me how to invest and save. He encouraged me to never stop learning. He never judged any of my stupid choices (and there were many!). He was the my foundation and pillar of strength. He was so intuitive!

My mother was not your typical mum. She was extremely funny (I got it from her for sure). She was strict but didn’t restrict me, you know? Like although she had her rules as I grew older and more rebellious she kinda gave in. I think she too wanted me to learn to navigate a world where women have to make their presence known and demand respect. Mum was what we call in Trinidad a real ‘saltfish’. She was loved by everyone and made space for them too. She was entertaining.

My both parents taught me grace and generosity. My mum taught me the power of prayer.

I am a lot like my mum; I give of myself a lot. I wear my emotions on my sleeve. I love a good joke and lots of old talk. I welcome people into my heart (too) easily.

I am also my dad’s daughter. I know what works best for me and I am not afraid to say it and draw deeply from my intuition.

Was there ever a time you almost gave up?
Hmmm…was there a time I almost gave up? Hell YES! After the death of my mum I remember thinking I can’t go on. My son was a year and a half and I was in the throes of postpartum (yeah, it can go on and on). My dad stood ground and held me down. Years later after I lost my dad I thought that was it! No more life to live. No reason to go on. No reason to smile. I stopped standup comedy and if I am being honest I think I stopped breathing for almost 5 years. Grief can take your breath away.

Alright, so if you are open to it, let’s explore some philosophical questions that touch on your values and worldview. Is the public version of you the real you?
Is the public version of me the real me? I would say the public knows a version of the real me. I mean, why would I even give them that power? lololol. What the public sees of me is the real me they just don’t see all of me, if that makes sense?

Okay, so let’s keep going with one more question that means a lot to us: Have you ever gotten what you wanted, and found it did not satisfy you?
Have I ever gotten what I wanted and found that it didn’t satisfy me? Have I ever?!?! Hahaha….yes! 100%.

Years ago I was in love with this guy and prayed that we would meet and get together. I mean, prayed! You hear me! I was like GOD, please, this guy is EVERYTHING I ever wanted. God was like…here you go my darling daughter. Months later I was JESUS! Please, this is not it! I am so sorry. Now my prayer to God is to grant me what he thinks is best for me. AMEN!

Contact Info:

Image Credits
Ricardo Reyes

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