About Cheryl Dillon


Cheryl Dillon, CPC | Founder of Funderful Experiences
Cheryl Dillon is a certified life coach, writer, speaker, and founder of Funderful Experiences, where she helps women create richer, more connected lives through personal growth, shared experiences, and community. She is also the creator of Connected Hearts – an in-person community in North County San Diego that brings women together for thoughtfully facilitated gatherings designed to spark fresh perspective, laughter, and lasting friendships. Through her newsletter, The Uplift, Cheryl blends storytelling, practical coaching insights, and a healthy dose of humor to help women navigate life’s transitions with greater confidence.
With a background in psychology and more than 16 years of coaching experience, Cheryl encourages women to see new possibilities, challenge limiting beliefs, and create lives that feel more joyful, connected, and authentically their own.
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
















