Meet Cheryl Dillon
For more than three decades, I’ve had the privilege of working with people during some of the most important moments in their lives and careers.
I’ve trained professionals, built businesses, coached individuals through major life transitions, facilitated difficult conversations and created experiences that bring people together.
For nearly two decades, I’ve worked alongside my husband and business partner at Equitable Mediation Services, helping people navigate the emotional and interpersonal complexities of separation and divorce. That work has given me a front-row seat to relationship dynamics, conflict and what can happen when relationships are under enormous strain.
What I’ve discovered across different roles, industries and reinventions is that one thing has remained remarkably consistent: the quality of our relationships shapes the quality of our lives.
I’ve seen it in business, where relationships create opportunities that no marketing strategy ever could. I’ve seen it in coaching, where one honest conversation can change the direction of a person’s life. I’ve seen it in communities, where people flourish when they feel welcomed, valued, and included. And I’ve seen it up close in my work with couples, where the way two people communicate, handle conflict and care for each other can shape the course of a relationship.
Bringing people together matters. But what fascinates me most is what happens next: the patterns we fall into, how we handle differences, how we repair when things go wrong and what helps relationships thrive.

Every Chapter of My Career Has Led to This One

Today, that perspective shapes everything I create through Funderful Experiences, from speaking and collaborations to my writing and Connected Hearts the women’s community I founded here in North County San Diego.
Education & Professional Training
- Certified Professional Coach (CPC)
- Graduate of the Institute for Professional Excellence in Coaching (iPEC)
- B.A. in Psychology, University of Connecticut
- Event Planning Certificate, San Diego State University
Showing Up in My Community
Since relocating to North County, I’ve made it a priority to contribute to the community I now call home.
I’m a proud member of the Carlsbad Chamber of Commerce, where I’ve gotten to know many of the entrepreneurs and business owners who make North County thrive.
I’m also a member of the Woman’s Club of Carlsbad, a commissioner on the city’s Senior Commission, a volunteer at the Carlsbad Senior Center, and previously volunteered at Rancho Coastal Humane Society, where I adopted my dog-ter, Wrigley.
These aren’t just resume lines. They’re what showing up actually looks like.



Celebrating the launch of Funderful Experiences with the Carlsbad Chamber of Commerce and some of the wonderful people who came out to support me.
A Little About Me
I spent most of my life in New Jersey, where I mastered the art of saying exactly what I’m thinking, followed by five years in Chicago (Go Cubs!). I’d wanted to live in San Diego my whole life, and in 2018, after one too many Chicago winters, I finally convinced Joe, my husband and best friend of more than two decades, that it was time to head west.
When I’m not working, you can find me singing, tending my garden, shaking up a craft cocktail or watching a Cubs game with Joe (sometimes all at the same time,) usually with Wrigley standing in front of me, toy in mouth, shaking it at me and making very clear that whatever I’m doing is less important than her.

Wrigley, taking a well-deserved break after all that toy mockery.