Leaning into Loss: 3 Lessons on Grief


You may not realize it, but life either has, or will, make you something of a hope vendor. Loss is all around us. It makes up at least 50% of life. At times, you’ve worn the hat of grief counselor for friends, family, and co-workers. I want to share some insight I’ve gained that might shine a light on these often immobilizing and confusing stretches.

A couple of years ago, I 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.

Here are three 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 small chance (less than 15%) they’re experiencing delayed grief, he/she is grieving in character, meaning— the way we normally do life is the way we also grieve.

As an Enneagram four, I grieve in all colors of the rainbow; with intensity and every shade of emotion. Hell, my feelings even have feelings, so this emotional intensity checks out in light of my baseline character.

Suffering is Optional

Pain is inevitable; suffering is optional.

Pain and loss are an integral 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 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?”

Resilience shines not when we deny our pain, but 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. In doing so, I cheapen their felt 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 how isolation wreaks havoc on the grieving soul. 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 write this, I’m 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? It’s a combination of two things: we stop to give thanks a lot more for the things we have that bring life, laughter, and meaning. We also explore in conversation 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,