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Meet Kaylee Cuthbertson of Always Eventful

Today we’d like to introduce you to Kaylee Cuthbertson.

Hi Kaylee, we’d love for you to start by introducing yourself.
I attended the University of South Carolina, where I earned a Bachelor of Science in Hospitality Management.
After graduating, I began planning events for friends and family simply for the joy of it. As I shared those moments on social media, inquiries began to follow. What started as a creative outlet quickly evolved into something more meaningful, and I realized I had the opportunity to build something of my own. I made it official, obtained my business license, and began taking on clients.

For the first three years, I balanced growing my business while working full time. It required significant time, energy, and dedication, but I remained focused on creating something I truly believed in. Eventually, I took a leap of faith and pursued Always Eventful full time, a decision that has proven to be incredibly rewarding.

Now, four and a half years in, Always Eventful has grown into a business I am deeply proud of. I am sincerely grateful for every client who has entrusted me with their celebrations. Being part of such meaningful moments is an honor I never take lightly, and it continues to inspire the work I do each day.

I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
The journey has not been without its challenges, but each one has played an important role in shaping both my business and who I am as an entrepreneur.
In the early stages, one of the biggest challenges was balancing a full time career while growing Always Eventful. It required long hours, sacrifice, and learning how to manage my time with intention. There were also moments of uncertainty, especially when it came time to step away from the stability of a steady job and fully commit to my business.

As Always Eventful continued to grow, new challenges followed. Learning how to set boundaries, refine my processes, and confidently communicate my value all came with time and experience. In an industry that is both highly competitive and deeply personal, there is a constant need to evolve, stay creative, and consistently deliver at a high level.

Looking back, those challenges have been some of the most valuable parts of the journey. They have strengthened my confidence, shaped my perspective, and helped me build a business that is both intentional and resilient.

Alright, so let’s switch gears a bit and talk business. What should we know?
Always Eventful is a full service event planning and design company specializing in weddings, while also offering planning for a wide range of celebrations including birthday parties, graduations, baby showers, wedding showers, rehearsal dinners, and welcome parties. While we love any reason to celebrate, weddings are truly at the heart of what we do.

We offer full planning, partial planning, and day of coordination services, allowing us to meet our clients exactly where they are in the process. Whether a client is looking for comprehensive guidance from the very beginning or support in the final stages to ensure everything comes together seamlessly, each service is designed to create a smooth, enjoyable experience from start to finish.

What sets Always Eventful apart is the combination of thoughtful design and a highly organized approach. Every event is carefully curated to reflect our clients in a way that feels elevated, cohesive, and personal, while also being executed with precision behind the scenes. Our clients trust us not only for how their events will look, but for how they will feel, knowing every detail is handled with care.

We are known for creating celebrations that feel effortless, yet deeply intentional. No two events are ever the same, and that level of personalization is something we value greatly. From intimate gatherings to large scale weddings, the goal is always to create an experience that is both beautiful and meaningful.

What I am most proud of, from a brand perspective, is the trust and relationships we have built with our clients. Being chosen to play a role in such important moments is something I never take lightly. Always Eventful is rooted in genuine connection, attention to detail, and a true passion for celebrating life’s most special occasions.

What makes you happy?
What makes me happiest is seeing everything come together and watching my clients fully enjoy the moments they have been looking forward to. There is something incredibly special about knowing that all of the planning, details, and behind the scenes work have created a space where they can be present and truly celebrate.

I also find a lot of joy in the process itself. I love taking an idea or vision and turning it into something tangible and beautiful. From the initial conversations to the final touches on event day, every step is an opportunity to create something meaningful.

More than anything, it is the people. Being a part of such important milestones in someone’s life is something I never take for granted. Whether it is a wedding, a milestone birthday, or a celebration of a new beginning, those moments carry so much emotion and significance. Knowing that I get to play a role in that is what makes this work so fulfilling.

Contact Info:

Image Credits
Image 1: Ashleigh Donahue Photography
Image 2: Stee Garman Photography
Image 3: Stee Garman Photography
Image 4: Loftus Photo & Film
Image 5: Todd Turner Photo
Image 6: Loftus Photo & Film

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