The Inspiration Behind Funderful Experiences

Ever notice how every brand, event, and workshop seems designed for the under-40 crowd? We sure did.

That’s why Funderful Experiences was created. As women in midlife, we’ve reached a stage of life where meaningful social bonds matter more than ever – but they can also be harder to form.

Our mission is simple: to embrace this powerful life stage by creating spaces where women rediscover joy, purpose, and genuine connection.

Our events offer valuable, expert-led learning on topics that matter right now – navigating midlife changes, wellness and personal development – all while fostering camaraderie through intentional activities designed to make meeting new people easier, more natural, and more likely to lead to lasting friendships.

Meet Your Host

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 a background in psychology, certification as a life coach specializing in life transitions, and training in event planning, I’m uniquely positioned to create remarkable experiences that matter.

When I moved to 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 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 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 will be crafted to feel like an exhale. No judgment, no pressure – just insightful learning, honest conversation, and the kind of laughter that reminds you you’re not alone. You’ll show up as you are, and leave feeling more like yourself. I can’t wait to welcome you. Let’s make this chapter your most Funderful yet!

The Power of 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.

In our Connected Hearts Membership, we’re building a community where women support each other and form lasting friendships through shared experiences.

From monthly membership gatherings to future special experiences, every event we create aims to help you make the most of this time in your life.

“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