We recently had the chance to connect with Kaitlyn Bennett and have shared our conversation below.
Kaitlyn, really appreciate you sharing your stories and insights with us. The world would have so much more understanding and empathy if we all were a bit more open about our stories and how they have helped shaped our journey and worldview. Let’s jump in with a fun one: What makes you lose track of time—and find yourself again?
When I’m creating art, I lose track of time and find my true self, free from stress, overthinking and life in general.
Can you briefly introduce yourself and share what makes you or your brand unique?
Of course! I’m Kaitlyn the hands behind all the lettered items at The Lettering Bar.
I’m a calligrapher, live lettering artist, and engraver based in Naples, Florida. I specialize in modern calligraphy for weddings, brands, and events of all kinds. Over the years, my work has popped up at celebrations across Southwest Florida and beyond — from dreamy destination weddings to elegant baby showers, dinner parties, galas, and corporate events. I also teach calligraphy workshops locally!
Thanks for sharing that. Would love to go back in time and hear about how your past might have impacted who you are today. What did you believe about yourself as a child that you no longer believe?
Like many creatives, I once believed that being an artist wasn’t a “real” job and that making a living doing what I loved just wasn’t possible. But over time, I realized that success doesn’t have to look one certain way. I chose to let go of that limiting belief, take the leap, and trust in my craft. That decision changed everything.
What fear has held you back the most in your life?
Just like the belief that I couldn’t be a “real” artist, I also carried a quiet fear of failure. What if I took the leap and it didn’t go well? What if no one connected with my work, or I made a mistake along the way? That kind of fear can weigh heavily on a creative heart. It took time, patience, and a lot of trust in myself to move through it but it’s been one of the most rewarding parts of the journey.
Next, maybe we can discuss some of your foundational philosophies and views? Is the public version of you the real you?
Yes, the version of me you see publicly is truly me. I couldn’t imagine showing up any other way or feeling like I had to pretend. Being an artist, to me, is all about staying connected to who you really are and creating from that place of honesty. That’s what I love most about what I do, the freedom to be fully myself and share that with others.
Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. What is the story you hope people tell about you when you’re gone?
When I’m gone, I hope I’m remembered for my authenticity, my passion, and the way I found beauty in the little things. I’ve always loved noticing what others might overlook adding meaningful details that turn ordinary moments or mementos into something special. Whether it’s a gift, a wedding, or a quiet gesture, those thoughtful touches are where the magic lives for me.
Contact Info:
- Website: https://theletteringbar.com
- Instagram: https://www.instagram.com/theletteringbar/
- Linkedin: https://www.linkedin.com/in/kaitlyn-bennett-06850928b/
- Facebook: https://www.facebook.com/theletteringbar
Image Credits
Stella Paschall
