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: Meaningful Connection. Personal Growth. Pure Joy.

Connected Hearts is our signature community experience, created for women who want deeper connection, personal growth, and more authentic relationships in midlife.

This is where connection meets real-life change – helping you think differently, feel better, and show up in your life in a way that feels more true to you.

Through thoughtfully facilitated gatherings and continued engagement throughout the month, members experience:

Conversations that go beyond small talk.

Guided reflection and discussion that helps you see things with fresh eyes, shift patterns that may be keeping you stuck, and make choices that feel more aligned with what matters most to you.

Shared moments that remind you how good it feels to simply be yourself.

The kind of connection that naturally opens the door to authentic friendships.

Designed to leave you feeling lighter, brighter, and more energized – not just for one evening, but all month long.

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

Not therapy. More than social.

I really cannot describe the feeling I had when I first experienced Connected Hearts. It was a lovely feeling of being taken care of for the first time in a long time.

Kelly S., Carlsbad

Funderful Experiences in Action

More than just events – these are experiences designed to help you relax, connect, and genuinely enjoy yourself.

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.