Leaning into Loss- 4 Lessons on Grief

“Resilience comes from deep within us and from support outside us. It comes from gratitude for what’s good in our lives and from leaning in to the suck.”
Sheryl Sandberg

I recently attended an all-day workshop led by David Kessler, self-help author and grief guru.  He is most well known for his groundbreaking work with Elisabeth Kubler Ross, a Swiss-American psychiatrist who pioneered what we know as hospice care as well as the Kubler-Ross model, or the five stages of grief (denial, anger, bargaining, depression, acceptance).

Despite Kessler’s expertise in death and grieving, he is hilarious. He cracked jokes throughout the entire day, poking fun at himself and taking some light-hearted stabs at the afterlife.  I found this profound in light of his work’s focus. 

It’s impossible to funnel all the takeaways into 500 words or less, but I’m going to do my best to share some punchy truths about grief that rocked me to the core. 

Here are four key insights to remember about grief and the grieving process: 

We Grieve in Character

Have you ever known someone who is super level-headed, maybe even annoyingly practical and even-keel, experience a major loss and recover with seamless resilience?  Perhaps to the point you even asked them, “Are you sure you’re okay?  You don’t even seem like this phased you!”  

Unless there is a very small chance (less than 15% I learned at the workshop) they’re experiencing delayed grief, he/she is grieving in character, meaning— the way we normally do life is the way we also grieve.  

Me, on the other hand, grieve all colors of the rainbow; with intensity and every shade of emotion.  However, as an Enneagram four, my feelings even have feelings, so this is par for the course. 

Suffering is Optional

Throughout the day, Kessler kept coming back to this truth bomb: Pain is inevitable; suffering is optional. 

Pain and loss are absolutely a part of life.  Suffering, however, is the story we make up about our pain.  For example, “This shouldn’t be happening to me” or “It wasn’t supposed to end this way.” We quickly forget how much a part of life loss is as the proverbial record gets stuck on that screeching note of overwhelming shock and awe.  

The upside to this is we have complete power over whether we suffer long-term or not.  When we suffer, we live in our heads and attach to narratives of futile embellishments…”why me?”  

This is where resilience shines center stage as we courageously “lean into the suck” as Sheryl Sandberg cleverly puts it in her latest book Option B.  Loss is painful, and the quickest way to the other side is through it, not around it.

Fixing Doesn’t Work

There is no rational way to fix traumatic loss just like there is no way of scientifically explaining romantic love.  It just is.  

Grief must be witnessed, not explained.  When I try to relate to someone in their grief by offering up a “me too,” what I’m doing is making it about me, not actively listening, and in doing so, cheapening their very real experience.  Don’t worry, grief will inevitably run its complex and necessary course.  We don’t have to, nor can we ever simply fix it.  A hug, an open ear, and a shoulder to cry on will work far better.

From my own experience, I’m reminded that isolation wreaks havoc on the grieving soul.  No, I’m not saying we need to extrovert-up and throw ourselves into social chaos. However, knowing we’ve got a few safe people who will witness our grief is vital. 

We’re not meant to go this road alone.


As I wrap up this recap, I am sort of cringing on the inside.  It’s so pat…so formulaic.  The grieving process is far from math.  It’s ghastly.  It feels like death.  It’s bigger than space and time and breaks us in a way that feels violent, wrong.  So how do we intentionally bring awareness to this part of life, even when what we currently experience feels light and joyful?  I think it’s a combination of two things: we give thanks a helluva lot more for the things we have that bring life, laughter, and meaning.  We also talk more openly about the reality of loss, not to focus on the negative, but mindfully acknowledge the fragility of it all.  These two go hand in hand.  

If you or someone you know is alone in their grief, know that there are options. Please reach out if your grief needs a witness. 

It won’t stop the pain, but it might ease the suffering.   

Love & Gratitude,