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 genuine 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 feel truly at home in themselves again.
Each Funderful Experience blends engaging activities, meaningful conversations, fresh perspectives, and just the right touch of self-exploration – all while fostering camaraderie in ways that make meeting new people easier, more natural, and more likely to lead to lasting friendships.
Because midlife isn’t for settling – it’s for soaring!
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 opportunities this stage brings.
With 15 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 remarkable experiences and meaningful community for women navigating midlife in North County San Diego.
One of my deepest values is inclusion. At different times in my life, I’ve known what it feels like to be left out – as a kid on the playground, as a newcomer to a city, even as an adult walking into a room where it seemed like everyone else already had their place. Those moments stick with you. They can reshape how you see yourself, alter the way you carry yourself, and sometimes keep you from the very connections you long for.
But they can also spark a deeper commitment: to create a space where no one ever feels that way.
When I moved to Carlsbad 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 was surprised by how tough it was to find my people. I didn’t have a built-in community, and suddenly the midlife changes I was feeling weren’t just physical – they were emotional, too. I didn’t want surface-level conversations. I craved connection.
Funderful Experiences came from that longing – for depth, joy, and a place to drop the mask. I wanted to create something where women like us throughout Carlsbad, Encinitas, and the surrounding areas could gather, grow, and feel truly seen – where authenticity matters more than appearances, and conversations go beyond small talk to something nourishing and real.
My promise to you is simple: every Funderful Experience is crafted to feel like an exhale. No judgment, no pressure – just insight, connection, and laughter that reminds you you’re not alone. Come exactly as you are, and leave feeling lighter, brighter, and more at home in yourself. Together, let’s make this chapter our most Funderful yet!
Local Community Commitment
I believe that true connection starts at home. After relocating to Carlsbad, 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. I also previously volunteered at Rancho Coastal Humane Society in Encinitas, where I contributed to animal welfare efforts in the area and where I adopted my dog, 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.
