My Story: Creating Authentic Community for Women in Midlife

Hi, I’m Cheryl Dillon, the founder of Connected Hearts. As a woman navigating midlife, I understand firsthand both the challenges and the opportunities this stage brings. With 16 years as a certified life coach specializing in life transitions, a background in psychology, and training in event planning, I bring both the heart and the structure to create gatherings where something real can actually happen.

Much of my professional life has centered on helping people through life’s turning points – whether coaching individuals through the emotional complexities of divorce or helping women gain clarity and the courage to create meaningful change in their lives.

I co-founded Equitable Mediation Services with my husband Joe – a nationally recognized divorce mediation practice that has deepened my understanding of life transitions and continues to inform the compassion and intentionality I bring to every Connected Hearts gathering.

 

A Turning Point

When I moved to Southern California in 2018 after spending most of my life in New Jersey, followed by five years in Chicago, I found myself reflecting on how I wanted this next stage of life to feel.

For me, midlife arrived not as a crisis, but as a powerful turning point – an invitation to look inward and intentionally design a next chapter rich with depth, joy, and new possibility, and to help other women do the same.

I knew what I didn’t want – surface-level socializing that left me feeling lonely and disconnected. What I craved was something real. Conversations that went somewhere. Women who showed up consistently enough that something genuine could actually grow between us.

I looked for that. I couldn’t find it. So I decided to build it.

Connected Hearts was born from that vision: to help women shape a midlife that feels purposeful, connected, and beautifully their own – filled with laughter, meaning, and true friendship. And to create a place where women could gather, grow, and feel truly seen – and where conversations go deeper than pleasantries into something nourishing and real.

The Power of Intentional Gathering

There’s something magical that happens when women come together with intention. I personally design and facilitate every gathering and pour everything I know as a coach and everything I believe about connection into each one.

After every evening, without fail, I watch something shift in the room.

Women who arrived a little guarded leave a little more open. Women who came in not knowing anyone leave with plans already made. Women who felt disconnected begin feeling more alive, more hopeful, and more themselves again.

That’s why Connected Hearts means so much to me – because what happens here changes something, for the women in the community and for me.

Midlife isn’t for settling – it’s for living fully!

Stay Connected

Writing is another way I show up – honestly and without the filter. If you want to know how I really think about midlife, connection, and this chapter of life, explore Real Talk.

And if you’d like a little encouragement and fresh perspective delivered straight to your inbox, The Uplift is free and delivered via email.

“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