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

The Power of Intentional Gathering

There’s something magical that happens when women come together with intention. Conversations deepen, laughter flows freely, and natural bonds form. This is why our approach centers on thoughtfully structured in-person experiences that remove the awkwardness of meeting new people.

Through Connected Hearts, we’re building a community where women support each other, grow, and form lasting friendships through meaningful shared experiences. And through private coaching, we offer a dedicated path for individual growth.

Every part of Funderful Experiences is designed to create the conditions for something most of us are quietly craving – genuine connection, real friendship, and a midlife that feels truly alive.

“This is the power of gathering: it inspires us, delightfully, to be more hopeful, more joyful, more thoughtful: in a word, more alive.”

– Alice Waters

Local Community Commitment

I believe that true connection starts at home. After relocating to California, I’ve made it a priority to engage with and support the incredible community around me. I’m proud to be an active member of the Carlsbad Chamber of Commerce, a local organization dedicated to supporting and growing small businesses, fostering connections, and strengthening the economic and social fabric of our community. Through my involvement, I have the privilege of collaborating with local entrepreneurs and community leaders throughout North County who share a passion for making this region thrive.

I’m also a member of the Woman’s Club of Carlsbad, a 100-year-old non-profit organization that unites women committed to community service and giving back to those in need. Through the Woman’s Club, I’ve witnessed firsthand the powerful impact of volunteer service and the bonds that are formed when individuals work together for the common good.

Additionally, I serve as a commissioner on the city’s Senior Commission and volunteer at the Carlsbad Senior Center, helping support and connect with our senior community. And previously volunteered at Rancho Coastal Humane Society in Encinitas, where I not only contributed to animal welfare but also adopted my fur daughter, Wrigley. These roles allow me to contribute to North County in ways that align with my passion for building meaningful connections and making a positive impact.