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 women shape a midlife chapter that feels joyful, vibrant, and fulfilling. She’s also the creator of The Uplift, a nationally read newsletter that blends 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 joy have the power to redefine this life stage. With a background in psychology and coaching, she brings a refreshing mix of real talk, warmth, and wisdom to conversations about friendship, identity, and how to truly thrive in midlife.
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






