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

Connect, gain fresh perspective, and experience midlife with more joy, depth, and possibility.

Cultivating Connection and Moments That Matter

In a world that often feels rushed, noisy, and disconnected, we’re creating something different.

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.

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, fresh insight, and practical tools 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.

Not therapy. More than social.

“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

More than just events – these are thoughtfully designed experiences that bring women together 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 transform uncertainty into your greatest opportunity, creating a clear, empowered path forward.

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 with 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.

Looking to bring fresh perspective on connection, midlife friendships, or life transitions to your group or audience?

Cheryl leads engaging talks and designs facilitated experiences that spark reflection, laughter, and moments of connection that stay with you long after the conversation ends.

She is also available for podcast interviews and special events.

Stay Connected with The Uplift

Occasional emails containing reflections, insights, and upcoming experiences.