Making Midlife Funderful: Connection, Community and Guided Gatherings for Women

Transformative experiences for women sparking a midlife alive with joy, meaning, and fresh possibility.

Cultivating Connection and Moments That Matter

In a world that often feels rushed, noisy, and disconnected, we’re building a place where conversations flow, laughter comes easily, and you’re reminded you’re not doing this season of life alone.

At Funderful Experiences, we believe genuine connection with others isn’t a luxury – it’s essential to our well-being, and to creating a midlife that feels vibrant, fulfilling, and fun.

Connected Hearts: Real connection. Fresh perspective. A next chapter you’re excited to live.

Not therapy. More than social.

Connected Hearts is our signature community for women who are choosing depth, growth, and joy in midlife.

Through thoughtfully facilitated gatherings and continued connection throughout the month, you’ll experience meaningful conversation and fresh perspective to help you shape a next chapter that feels energizing, fulfilling, and truly your own.

Connected Hearts is an in-person community in North County San Diego, with an online community launching soon.

“A fun, uplifting evening that left me with that special feeling that lingers after getting together with a group of great women for the kind of talking and laughing you do when you get together away from work, family, etc. You get to be the self that perhaps others don’t get to see out of the usual context.”

Melissa F., Vista

Funderful Experiences in Action

Every experience is thoughtfully designed to create genuine connection and shared moments of joy.

Personalized Midlife Coaching

Midlife often brings change – and with it, new questions. Whether you’re navigating an empty nest, contemplating a career change, newly retired, divorced, or simply feeling that your own needs have been on the back burner for too long, private coaching offers a dedicated space to find clarity on what’s next.

Together, we’ll get clear on what you actually want – and build a path to get there.

Your Guide to a More Funderful Midlife

Hi, I’m Cheryl Dillon, a certified life coach specializing in life transitions and the founder of Funderful Experiences. I design experiences that bring women together in a way that feels real, help them cultivate genuine connection with themselves and others, and rediscover the joy that makes life feel truly Funderful.

I believe this chapter of life is meant to feel vibrant, authentic, and expansive – yet many women feel busier, more isolated, and less fulfilled than ever.

That’s why I created Funderful Experiences – because what most of us really crave isn’t more scrolling or small talk, but time that genuinely fills us up.

Through coaching, community, and shared experiences, my goal is simple: to help women feel supported, energized, and excited about what’s ahead.

Want to give your audience a conversation they’ll still be thinking about on the drive home?

Cheryl leads engaging talks on connection, midlife friendships, and life transitions — and designs facilitated experiences that spark reflection, laughter, and the kind of moments that stay with you long after the room clears.

Cheryl is also a guest for podcast interviews and available for special events. Reach out to start the conversation.

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