What if the most painful part of grief isn’t the loss itself, but the belief that you’re doing it wrong?

That quiet voice that says you should be further along… that you should be handling it better… that somehow, if you had done one thing differently, they might still be here…

I hear that voice every single day in my work. And I’ve felt it in my own grief too.

But here’s the truth: you’re not doing grief wrong. We’ve just been taught to understand it wrong.

In this episode, I’m joined by David Kessler, one of the world’s leading grief experts, known for his work on the five stages of grief alongside Elisabeth Kübler-Ross, and the author of Finding Meaning: The Sixth Stage of Grief.

But to me, David isn’t just an expert.

He’s a friend. And he’s the man who stood in my backyard less than a week after my son Sammy died… who sat with my husband and my youngest son, holding our fear and our shame without trying to fix it.

When I felt called to go deep into the redwoods to face my own darkness, David was the one who said, “I’ve got them.”

He supported my family then, and he remains a steady presence in our lives today.

David Kessler isn’t just a grief authority. He’s someone I deeply trust.

In this conversation, we pull back the curtain on what healing actually looks like beyond the myths and the stages we’ve been sold. We explore why grief is never linear, why acceptance isn’t a finish line, and why meaning doesn’t come from the death itself, but from the life you live afterward.

We explore: 

• Why the pressure to “move on” actually keeps people stuck in grief

• What the sixth stage of grief really looks like beyond the theory

• The subtle mistake people make when trying to “find meaning” too soon

• Why grief has no timeline, and what to trust instead

• A powerful reframe for guilt that can instantly soften self-blame

• What we misunderstand about “prolonged grief” and why it matters

• Why old wounds resurface during loss and how to work with them

• The difference between surviving your grief and being transformed by it

• One belief about healing that quietly holds so many people back

• How even the most traumatic loss can eventually become something sacred

Don’t forget to check out David’s work at grief.com. His new workbook, Finding Meaning, is available at griefbook.com and comes with a free three-part class to help walk you through it. 

As always, I want to hear from you. Share your story or send questions to cryingoutloudpod@gmail.com. And if you need a place to connect with people who truly get it, visit the Grief Healing Collective. None of us were meant to do this alone. Let’s cry out loud together.