Our Story: Creating Authentic Community for Women in Midlife
Ever notice how so many brands, events, and workshops seem designed for the under-50 crowd? We sure did.
That’s why Funderful Experiences was created. As women in midlife, we’ve reached a stage where real connection, fresh inspiration, and moments of joy matter more than ever – yet they can also feel harder to find.
Our mission is simple: to embrace this powerful life stage by creating spaces where women rediscover what lights them up, explore new possibilities, and cultivate a renewed sense of self.
Each Funderful Experience blends meaningful conversations, insightful perspectives, and just the right touch of self-exploration – all while fostering camaraderie in ways that make connecting with like-minded women more natural and more likely to lead to lasting friendships.
Because midlife isn’t for settling – it’s for living fully!
Meet Cheryl Dillon: Life Coach & Midlife Connection Expert
Hi, I’m Cheryl Dillon, the founder of Funderful Experiences. As a woman navigating midlife, I understand firsthand both the challenges and the opportunities this stage brings.
With 16 years as a certified life coach specializing in life transitions, a background in psychology, and training in event planning, I’m uniquely positioned to create joy-filled experiences that inspire genuine growth and connection.
When I moved to Southern California in 2018 after spending most of my life in New Jersey (where I mastered the art of saying exactly what I’m thinking) and five years in Chicago (Go Cubs!), I found myself reflecting on how I wanted this next stage of life to feel.
For me, midlife arrived not as a crisis, but as a powerful turning point – an invitation to look inward and intentionally design a next chapter rich with depth, joy, and new possibility, and to help other women do the same.
Funderful Experiences grew from that vision: to help women shape a midlife that feels purposeful, connected, and beautifully their own – filled with laughter, meaning, and genuine friendship. I wanted to create something where women like us could gather, grow, and feel truly seen – where authenticity matters more than appearances, and conversations go beyond small talk to something nourishing and real.
Today that vision has taken shape through two distinct pathways: Connected Hearts – a community for midlife women, currently gathering in-person here in my home of North County San Diego, with an online community launching soon for women everywhere – and private coaching, for women ready to gain clarity, build confidence, and create a next chapter that feels truly their own.
Writing is another way I show up – honestly and without the filter. If you want to know how I really think about midlife, connection, and this chapter of life, explore Real Talk.
My professional life has always centered on helping people through life’s turning points – whether that means coaching individuals through the emotional complexities of divorce or helping women gain clarity, build confidence, and the courage to create lasting change in their lives.
I also co-founded Equitable Mediation Services with my husband Joe – a nationally recognized divorce mediation practice that has deepened my understanding of life transitions and continues to inform the compassion and intentionality I bring to everything I create at Funderful.
Every Funderful Experience is designed to feel like an exhale – a place where you can be yourself, connect in real and rewarding ways, and leave feeling lighter, brighter, and more alive.
Together, let’s make this chapter our most Funderful yet!
Qualifications & Education
- Certified Professional Coach (CPC)
- Graduate of the Institute for Professional Excellence in Coaching (iPEC)
- B.A. in Psychology, University of Connecticut
- Event Planning Certificate Program, San Diego State University
