Meet Kelly Boyle

 

We recently connected with Kelly Boyle and have shared our conversation below.

Kelly, so good to have you with us today. We’ve always been impressed with folks who have a very clear sense of purpose and so maybe we can jump right in and talk about how you found your purpose?

Growing up I thought finding my purpose would be a single, defining moment. I envisioned it as a light bulb going off that lit up the path ahead. However, for me, it wasn’t about discovering my purpose in a single moment. It was about gradually uncovering my creative side and embracing what I truly love, even when it didn’t align with what I was ‘supposed to do’ in my career

I had a job offer to join an event planning firm after graduating with my MBA in 1994, but I turned it down and spent most of my career in corporate finance. At the time, wedding and event planning wasn’t the booming industry it is today. A career in finance felt practical, safe, and aligned with societal expectations. So, I followed that path, even though something inside me longed for something different.

For the next 25 years, I had a “successful” career by many standards: climbing the corporate ladder, living and working abroad, and achieving milestones that others might view as the pinnacle of success. Yet, despite these accomplishments, I never felt completely fulfilled.

The creative pull was always there so I planned office events, organized celebrations for family and friends, and wrote concert reviews. While I was finding outlets for my creativity, I never imagined leaving my corporate job. Life, however, made it impossible to ignore this desire.

Over three years, I was laid off twice and fired once. It was a humbling and disorienting time, but it felt like a sign that I was supposed to change paths and do something different. I kept asking the universe, ‘What am I missing?’

With the guidance of a coach, I finally gave myself permission to listen to that quiet voice inside of me. I asked myself a simple yet powerful question: What do I really want out of life? I realized that the work I had been doing on the side was my purpose all along. At 47, I decided it was time to leap into the world of being a business owner. That was when LeslieJames Events was born.

Looking back, it wasn’t about finding my purpose; it was about allowing myself to pursue it, even when the path seemed uncertain and the voices of doubt and societal norms were loud. I could have started back in 1994, but the corporate experiences I had made me ready to embrace this next step.

Great, so let’s take a few minutes and cover your story. What should folks know about you and what you do?

LeslieJames Events specializes in creating luxurious celebrations that feel personal and meaningful to my clients. I plan everything from weddings to baby showers to anniversary parties. In the early planning stages, I take a lot of time to get to know my clients and their story. It is my goal for every detail of their event to feel intentional to leave a lasting impression no matter what service they have booked.

What excites me most is the ability to craft events that go beyond just being beautiful. I believe that every celebration is about more than just aesthetics – it’s about shared experiences, emotional moments, and the people who matter most. There is nothing more fulfilling than transforming a couple’s or client’s vision into something magical while building lasting relationships along the way.

The name LeslieJames Events is inspired by my parents. Since I was a little girl they have always brought magic to every family event and holiday. I learned that every moment is worth celebrating! Leslie, my beloved mother, may not be with us today, but her spirit lives on in every event we plan. My father, James, continues to be the life of every gathering, infusing joy into the simplest moments. I am actually called “Leslie” quite often, and I don’t mind. It serves as a gentle reminder of my mother and the purpose of this business.

Looking ahead, I’m excited to focus on full-service planning. This service helps clients from start to finish to improve logistics and truly get to know them and their families on a deeper level.

I’m also introducing a new offering—Venue Sourcing & Budgeting. This is designed for clients who may not have resources for a full-service planner, but desire a strong planning foundation. This new service offers clarity and confidence during the beginning phases of the planning process, tackling two of the most challenging aspects: money and location.

I also see LeslieJames Events expanding beyond New England – blending my love of travel and passion for events.

There is so much advice out there about all the different skills and qualities folks need to develop in order to succeed in today’s highly competitive environment and often it can feel overwhelming. So, if we had to break it down to just the three that matter most, which three skills or qualities would you focus on?

Looking back, three qualities have been foundational to my entrepreneurial journey: resilience, trusting myself, and my sense of humor—my ultimate superpower.

Long before I launched LeslieJames Events, resilience was my constant, guiding me through life’s challenges—from losing my mom during my junior year of college to building a career in the male-dominated world of corporate finance and eventually transitioning out of it, moving abroad twice, and embracing every adventure independently. Each challenge shaped me, teaching me to adapt, persevere, and trust my inner strength.

When I started LeslieJames Events just a year before the pandemic, resilience became more critical than ever. The pandemic forced countless event cancellations while the world was in turmoil. Then came the event boom, with everything colliding at once. The highs and lows pushed me beyond what I thought was possible, strengthening my resolve.

I’ve learned that success isn’t about avoiding failure but embracing it with grace and grit. Setbacks are inevitable, but trusting myself and finding humor—even in the toughest times—has allowed me to navigate the rollercoaster of life and entrepreneurship with hope and resilience.

Trusting myself has been equally crucial, particularly when I made the leap from corporate finance to event planning. During the height of COVID, when many around me worried and suggested it was “time to get a job,” I knew, deep down, I was on the right path. Despite the uncertainty and external pressure, I trusted my instincts and rode the wave. That trust has since translated into tangible success, turning me into an award-winning planner who is respected in the industry and has a full calendar of clients I truly adore.

Lastly, my sense of humor has been my greatest ally. Life is unpredictable, and it’s my humor that keeps me grounded and energized. It’s what allows me to laugh at the unexpected, lighten the load during stressful moments, and approach each challenge with a positive mindset. Humor reminds me that it’s not just about the destination, but enjoying the journey along the way.

For those just starting out, my advice is straightforward: follow your gut and humor will make the ride far more enjoyable! The road may not always be smooth, but finding joy along the way is what makes it all worth it.

Thanks so much for sharing all these insights with us today. Before we go, is there a book that’s played in important role in your development?

Two books have played an important role in my growth as a business owner: The Gifts of Imperfection by Brené Brown and Unreasonable Hospitality by Will Guidara.

In The Gifts of Imperfection, Brené Brown talks about the power of vulnerability, courage, and self-compassion. One of the most impactful takeaways for me was the idea that we don’t have to be perfect to be worthy of love and belonging. It’s certainly hard to let go of perfectionism on someone’s big day, but I have learned to prepare extensively leading up to an event and then let the day unfold naturally.

Unreasonable Hospitality by Will Guidara is all about exceeding expectations and going above and beyond for people to create experiences that make others feel seen and valued. The most valuable nugget from this book was Guidara’s perspective on customer service—how every interaction should leave someone feeling better than when they arrived.

The idea of being “unreasonably hospitable” has influenced how I approach every interaction not only with my couples but with all of their family, friends, and vendors at every event. I love to make everyone feel seen and that they will be taken care of. I think this has been one of the biggest reasons for my success! This is at the heart of what I do!

Contact Info:

Image Credits

Boston branding Photographer
Alex Gordais Photography
Julia Luckett Photography

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