my story: the journey behind the work

I’m so glad you’re here.

This space has long held pieces of my heart — first as a personal blog, and now as a quiet place for reflection. For those who want to understand the journey behind the work I do today, this page offers a bit of context — because lived experience has a way of shaping how we lead.

My name is Cassandra — most people call me Cass or Cassie — and for many years, writing was how I made sense of a very full life.

where it began

I began sharing my life online in 2009, during a season that was equal parts exciting and overwhelming. I was newly engaged, navigating a long-distance relationship while my fiancé was in the State Police Academy, finishing graduate school, and working for the State Appellate Court — all while my family was walking through significant change.

Planning a wedding during that time felt daunting and lonely. Writing became a place to process, learn, and organize the chaos. I poured myself into understanding weddings from the inside out — studying every guide, every detail, every moving part — not knowing then that this season was quietly shaping the foundation of my future work.

choosing a different path

After we were married in 2012, I found myself increasingly drawn to helping other couples navigate the wedding planning process. I began assisting planners in Springfield and St. Louis, and it became clear that my natural inclination toward organization, thoughtful design, and steady leadership brought me a sense of fulfillment I hadn’t found elsewhere.

What started as curiosity grew into clarity.

With encouragement from family and a growing belief that this work mattered, I launched Cassandra Dattoli Events in November of 2012. Over the next several years, as the business evolved and grew, I made the difficult and meaningful decision to step away from a career in the legal system — closing one chapter to fully step into another.

sometimes on the way to a dream, we get lost & find a better one

life that deepened the work

Life, of course, didn’t slow down.

Alongside building a business, building our first homes, walking through loss, we navigated a long season of infertility, welcomed an exchange student into our home, welcomed a little miracle and learned — again and again — how much patience, perspective, and grace matter when life feels uncertain.

Those experiences didn’t just shape who I am personally; they deeply influenced how I show up professionally. They taught me how to stay calm under pressure, how to honor emotion without letting it overwhelm, and how to lead with empathy, steadiness, and intention.

how this shows up today

Today, I serve as Creative Director & Lead Wedding Planner, guiding couples through a planning experience rooted in clarity, cohesion, and care. My work is informed not only by years of experience in weddings and floral design, but by a life that has required adaptability, discernment, and trust in the process. Growing up in a flower shop - helped too.

My story matters only in that it allows me to hold yours with respect.

Weddings are not just events — they are moments of meaning, legacy, and transition. My role is to help create space for those moments to be felt, honored, and remembered.

Thank you for taking the time to read a little of my journey.
I’m truly grateful you’re here.

With love,
Cassandra