My daughter will likely be spending Christmas 2026 in Colombia with her boyfriend’s family.
This will be the first time in 25 years that my little family of four won’t all be together for the holidays.
Before you roll your eyes at me, please know that I am acutely aware of how lucky I am to have had those 25 Christmases. And I’m truly overjoyed that she’s found this beautiful, talented man and that they make each other happy - that they bring each other peace.
But I cry every time I think about it anyway.
I’m grieving the end of that particular chapter in my life.
There’s a lot to grieve in mid-life.
So many changes.
So many endings.
Some of the things we grieve are micro in scale - like my holiday pangs. Some of it is bigger - identity changes around retirement, divorce, our aging bodies.
And some of it is enormous - major health challenges, the passing of someone we loved.
But here’s the thing nobody tells you about grief.
It has a shape.
And how you move through that shape determines whether it stays a chapter, or becomes the whole book.
Last week one of my clients literally screamed, “I have fucked up absolutely everything. And I’m never getting any of it back. I’m old, and I’m tired and I have completely lost at the game of life.”
She’s grieving the life she didn’t have.
She’s grieving the things she wished she’d done differently.
She thought she was telling me the truth about who she is and what is and isn’t possible for her.
She wasn’t.
She was grieving, and had no idea.
And that’s the funny thing about grief - it’s very good at masquerading. It takes the facts from our lives and contorts them into a verdict that feels like the truth.
Not “I’m sad about what I didn’t get to have,” but “I lost at the game of life.”
Grief doesn’t just make us feel bad. It makes us feel certain - certain about things that aren’t actually certain at all. And until we process it, it seeps into everything else, flattening it, souring it.
We mistake the shadow it creates for the whole sky.
But it can be processed. And the shape of that process is the same whether the grief is micro or macro - with one caveat: grief that’s tangled up with old trauma also needs body work, it needs nervous system regulation.
Today, we’re just talking about grief in general though, and I’ll share a story with you to illustrate what the shape of processing grief looks like.
If you know me, you’ve heard the story before: Grandma Annie, when her brother - my Uncle Henry - died.
Annie was Sicilian and she was, by nature, dramatic.
When my grandmother grieved (her brother or any other loss), she wailed - she weeped - she pulled her hair.
AND THEN SHE’D STOP and go back to whatever she was doing.
My father called her a phoney.
And given that between his German father and English mother he’d never seen anything even remotely like Annie, one could understand why.
But Annie wasn’t a phoney, and in fact, when it comes to healthy processing, she was a pro.
She’d feel a wave coming - there’s almost always a physical signal, pressure behind the eyes, a tightening in the throat, a punch to the gut. Annie would ride the wave: scream, pull her hair, weep, wail: “Henry! Henry!”
In a minute or two - it’s typical for intense emotion to crest and dissolve in a couple of moments - it would pass.
And Annie would pick up the Daily News from her lap, “Oooh, the Yankees are playing tonight.”
When the next wave came, she’d start in again at the top.
Eventually the space between the waves expanded, the intensity lessened and life grew around it. All in all, Annie had a pretty happy life.
Most of us didn’t learn to grieve that way.
Some of us learned to stuff it down, grin and bear it - and then wonder why everything feels a little blunted and grey. Some of us learned to live inside of grief, to hold it like a talisman of love, duty, or responsibility.
Annie was an anomaly in our family. All too often, I watched as my aunts passed stories of their suffering between them like trading cards - as if there was something to win from an identity built on loss.
Their grief was all consuming - they didn’t ride the waves as they came - they fought them. It never mattered whether they were grieving death, money, health or time - the fight always sounded the same. “Why, why, WHY? It should never have been this way. This is no life.”
That fight couldn’t dissipate the wave, it fed it. The grief intensified instead of cresting. And because they were always standing in it, the trading cards piled up.
The bad knee.
The ungrateful child.
The trip to Rome that would never be coming.
In the Annie model, life grows around grief - it becomes bigger and richer as grief processes and heals.
In the Aunts model, life remains inside of the grief and grief is what grows, swallowing more and more of what might have been possible.
Same wave. Two entirely different endings.
My client is in the middle of learning this - starting to recognize that “I lost at the game of life” isn’t a verdict, it’s a wave. That doesn’t undo decades of living inside her grief overnight. But naming it for what it is, is the entry point for processing it.
For me and my empty chair this Christmas - I already know how it will go.
The waves will come and I’ll let myself ride them. Sometimes I’ll get misty, and sometimes (probably in December when the decorating starts) I’ll downright ugly cry.
When each wave passes though, I’ll remember the Yankees and get right back to what’s in front of me.
Other times - like right now for instance - I’ll imagine her traveling for the holidays with the love of her life on her arm - and I’ll weep, full on, but my heart will be filled with joy.
If grief, disappointment, or an old story has started to sound suspiciously like the truth about your life, this is the kind of thing we untangle in private coaching.
The first step in moving forward is being able to see what you’re standing inside of clearly enough that the next step becomes possible.
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