About Cheryl Dillon


Cheryl Dillon, CPC – Life Coach & Founder, Funderful Experiences
Cheryl Dillon is a life coach and founder of Funderful Experiences, home of Connected Hearts – a community of midlife women shaping 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, happiness, 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
Letting Others in: Why Asking for Help is a Strength in Midlife
The Power of Small Wins in Midlife: Finding Joy in Everyday Moments
When Pain Becomes Power
The Joy of Being Truly Seen in Midlife Friendships
When a Life Role Ends in Midlife: Rediscovering Who You Are in Act Two
Are You Living by “Should” – or by Choice?
When Life Sideswipes You in Midlife
Podcast: Why Being a Friend to Yourself Changes Everything in Midlife
Why Saying No is One of the Most Powerful Acts of Self-Care in Midlife
Why Fun Isn’t Optional Anymore (Especially in Midlife)
Why Friendship in Midlife Feels Different – and Why it Matters More Than Ever
When Trying Something New in Midlife Feels Scary – and Exactly Why That’s a Good Sign
When Small Talk Isn’t Enough Anymore
When You’re Doing it All, but Missing What Matters
Midlife Personal Growth Can Trigger Others – and Why That’s Okay
When Comparison Creeps in: How to Reclaim Your Midlife Confidence
Choosing Authenticity in Midlife: Showing Up as Your Real Self
















