Making Midlife Funderful: Curated Gatherings, Coaching, and Community for Women

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

Cultivating Connection and Moments That Matter

In a world that feels increasingly disconnected – full of digital noise and surface-level interactions – we’re creating a different kind of space.

A space where you can put down your phone and lift your spirit. Where conversations go deeper than small talk, and laughter is shared, not typed with emojis.

At Funderful Experiences, we believe real, face-to-face connection isn’t a luxury; it’s essential to our well-being – and a midlife that feels vibrant, inspiring, and fun.

Connected Hearts Membership: A New Kind of Gathering, Thoughtfully Designed

Our signature program is Connected Hearts – a membership for women in midlife featuring professionally facilitated monthly gatherings that blend engaging activities, meaningful conversation, and just enough personal growth to stir something new.

Each month, women from Carlsbad and coastal North County San Diego come together for evenings that:

Offer a refreshing balance to the busyness of life;

Go beyond “updates” to sharing real stories;

Spark new ideas and a renewed sense of self;

Open the door to genuine connections and lasting friendships.

These evenings are designed to leave you lighter, brighter, and more energized all month long. Best of all, they’re as easy to say yes to as they are to look forward to.

It’s not therapy. It’s more than social.

It’s a new kind of gathering – for a new chapter of life.

I really cannot describe in words the feeling I had walking into that room. Everything was so beautifully designed… it was just a lovely feeling of being taken care of for the first time in a long time.

Kelly S., Carlsbad

This is What Real Connection Looks Like

More than just events; a space to show up as you are, to feel seen, laugh freely, and to remember what it feels like to truly connect.

What a lovely evening! The gathering was warm, well-organized, and beautifully planned to encourage meaningful conversation and authentic connection. I met several amazing women and left feeling energized and supported. It was such an empowering and thoughtful experience.

Vicky K., Carlsbad

Personalized Midlife Coaching Available Nationwide

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

Together, we’ll transform uncertainty into your greatest opportunity, creating a clear, energizing path forward.

Your Guide to a More Funderful Midlife

Hi, I’m Cheryl Dillon, a certified life coach specializing in midlife transitions and the founder of Funderful Experiences. I created this community because I believe that in this stage of life, genuine connection and moments of joy matter more than ever – yet can feel harder to find.

In a world that’s so noisy and surface-level, I wanted to cultivate a space that feels real again – because what most of us really crave isn’t more scrolling or small talk, but time that fills us up.

A place where we can connect face-to-face, share meaningful experiences, and remember what it feels like to truly belong.

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