Today we’d like to introduce you to Kaitlyn Bennett.
Hi Kaitlyn, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
My story starts with my personal passion for art and creativity quickly evolving into a thriving business rooted in the belief that even the simplest objects can be transformed into something meaningful and beautiful with a bit of hand lettering!
From an early age, creativity served as a way for me to relax, unwind, and express myself. I found comfort in the process of creating—something that continues to influence my work today.
About five years ago, I discovered calligraphy and was instantly drawn to its elegance and intentionality. As my skills grew, so did my desire to push beyond traditional pen and paper, which lead me to exploring engraving, heat foiling and debossing.
Today, as a professional calligrapher, live lettering artist, and engraver based in Naples, Florida, my work spans custom commissions, brand collaborations, and live, on-site personalization experiences where I create one-of-a-kind pieces in real time. From engraving glass and metal to lettering on leather and paper goods, my artistry has a modern yet timeless aesthetic.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It definitely hasn’t been an easy road. Any artist understands what it takes to push past the fear of being seen and deal with the pressure to perform. For me, getting over the anxiety of creating while being watched—especially during live personalization—was a real struggle. There’s little to no room for error in those moments, so building the confidence to handle that took time.
Appreciate you sharing that. What else should we know about what you do?
I’m a calligrapher and live event artist, and I specialize in modern calligraphy, engraving, and on-site personalization for weddings, corporate events, and brand activations. A lot of what I’m known for is creating those live, in-the-moment experiences—taking something simple and turning it into something meaningful right in front of people. Whether it’s engraving on glass, lettering on leather, or working on more unconventional surfaces, I love pushing beyond the expected and making each piece feel personal and intentional.
What I’m most proud of is being able to turn something I started out of pure passion into a business that’s worked with both individuals and major brands, while still keeping that hands-on, detailed approach. Every piece is done by me, and there’s a lot of care that goes into making sure it doesn’t feel mass-produced or impersonal.
What really sets me apart is that combination of artistry and experience. I’m creating live and on a wide range of materials, and still making it feel elevated and effortless. That ability to adapt in the moment, connect with people, and deliver something custom on the spot is something I’ve really had to grow into, and I think that’s what makes the work stand out.
Risk taking is a topic that people have widely differing views on – we’d love to hear your thoughts.
Saying yes to live events early on felt like a huge leap—putting my work out there in real time, with people watching and no room for mistakes, wasn’t exactly comfortable. But I knew that if I wanted to grow, I had to lean into that discomfort.
I’ve also taken risks in the way I’ve grown my business and artistry. By investing in new tools, experimenting with different materials like glass and leather, and stepping into spaces like brand activations without always knowing exactly how things would play out. A lot of it has been figuring things out as I go and trusting that I’ll rise to the occasion.
Contact Info:
- Website: https://theletteringbar.com
- Instagram: @theletteringbar
- Facebook: https://facebook.com/theletteringbar
- LinkedIn: https://www.linkedin.com/in/kaitlyn-bennett-06850928b/
