About Cheryl Dillon


Cheryl Dillon, CPC – Certified Life Coach, Writer, & Founder of Funderful Experiences
Cheryl Dillon is a life coach, writer, and founder of Funderful Experiences, home of the Connected Hearts membership – a community helping midlife women shape a chapter that feels joyful, vibrant, and intentional. She also writes The Uplift, a nationally read newsletter blending storytelling, coaching, and humor to help women reconnect with themselves and each other – bringing more laughter, purpose, and heart to everyday life.
Cheryl’s work centers on the belief that genuine connection, meaningful experiences, and personal growth bring depth, joy, and fulfillment to midlife. With a background in psychology and coaching, she brings warmth, insight, and real talk to conversations about friendship, identity, midlife transitions, and what it means to live fully and thrive in this season of life.
More Posts by Cheryl Dillon
The Power of Genuine Friendship in Midlife
It’s Not Too Late to Try Something New
Why Real Conversation Feels So Rare (and How to Bring It Back)
When Your Life is Full but Your Heart Feels Empty
Midlife Isn’t a Phase – It’s a Becoming
When Comparison Creeps in: How to Reclaim Your Midlife Confidence
The Courage to Be Seen: How Authenticity Builds Real Connection in Midlife






