When the Holidays Stir Old Grief You Thought You Buried
- Updated: November 4, 2025
Do you like snow globes? I know—they’re everywhere at tourist stops, glittering with nostalgia. Inside that little glass world, everything looks serene until someone shakes it. Then it’s chaos—flakes flying, beauty blurring, calm turned into confusion.
Do you like snow globes? I know—they’re everywhere at tourist stops, glittering with nostalgia. Inside that little glass world, everything looks serene until someone shakes it. Then it’s chaos—flakes flying, beauty blurring, calm turned into confusion.
As I wrote in The Lie of the Finished Leader, composure without honesty isn’t leadership—it’s leakage dressed as strength.
The holidays have a way of testing that truth.
✨Truths You Need to Know
Why Grief Is Normal
We’ve been sold the idea that if we just stay productive or “grateful,” we’ll outrun what hurts.
But as I unpacked in Healing Myths That Keep High-Functioning People Quietly Hurting, performance culture doesn’t heal—it sedates.
The holidays simply pull the sedation off.
Yet the world has always had seasons of emotional upheaval — but modern culture has industrialized it.
🔹 In ancient times: dysregulation came in cycles.
War, famine, plagues, upheaval — then recovery.
Communities mourned together: through ritual, fasting, wailing, prayer, movement.
There were elders. There was slowness. There was space for silence.
People expected hardship — and made room for communal repair.
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🔹 Now: dysregulation is constant — and monetized.
Our attention is hijacked 24/7.
There’s no off switch.
Algorithms thrive on shock, urgency, outrage.
Emotional chaos has become a business model — from cable news to “therapy-Tok.”
Capitalism doesn’t mind your pain; it profits from your distraction.
As Louis C.K. recently said in an interview about his novel Ingram, the American experiment keeps proving that “if you give people more and more, they just start getting more and more depressed and distant from their feelings.” So we coat the emptiness with distraction and pleasure—and pleasure only makes us want more.
And it’s showing up everywhere. A 2023 survey found that 61% of Americans expect to feel sad or lonely during the holidays, proof that distraction hasn’t healed us—it’s hollowed us.
We’ve lost our margins.
There’s no Sabbath, no pause that isn’t punished.
No elders guiding us — only influencers, burnout prophets, and algorithm tweakers.
We are emotionally underdeveloped but overstimulated.
That’s a dangerous combination.
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And the most dangerous part?
We’ve normalized the dysregulation so deeply that…
🧠 Anxiety is mistaken for personality.
🏃🏽♀️ Hustle is mistaken for virtue.
😐 Numbness is mistaken for adulthood.
So if you find yourself feeling heavy while everyone else looks merry, you’re not behind — you’re simply awake.
Your nervous system is telling the truth about a world that forgot how to grieve.
Why Unaddressed Grief Hits Leaders Harder
Grief doesn’t always announce itself as loss.
Sometimes it hides inside competence.
For high-functioning people, the ache doesn’t show up as tears — it shows up as control, perfectionism, or exhaustion that no amount of sleep fixes.
Let me show you what that looks like.
Opal’s Story
On the surface, Opal looked polished — calm, articulate, in command.
When I once asked if she’d always carried herself this way, she smiled and said quietly, “Not even close.”
“When I was fifteen,” she told me, “I was the late bloomer. The acne, the braces, the boy I secretly liked — Gary — and the winter contest the boys started at school.
They voted on who was the ‘ugliest girl.’
And guess who won?”
She laughed, but her eyes didn’t.
“They even taped a distorted drawing of my face next to my locker. I cried through Hanukkah and New Year’s. I swore I’d never be caught off guard again.”
Decades later, as she baked cookies with her daughter during winter break, that old humiliation broke through the frosting.
It wasn’t the flour that made her eyes sting — it was memory.
She wasn’t crying over Gary anymore; she was grieving the teenage girl who thought her worth could be voted on.
Jake’s Story
Then there’s Jake — sharp, successful, disciplined.
Graduated mid-winter with honors but no job offers.
Watched his friends launch careers while he mailed résumés that never got replies.
He buried the fear under ambition.
Fifteen years later, he’d built a thriving copywriting firm — until 2008 hit.
Laid off. Mortgage in jeopardy.
He told himself, “I’ll never feel that powerless again.”
So he rebuilt, bigger and leaner.
Then came 2025.
AI reshaped his industry overnight.
Clients vanished, rates plummeted, and suddenly the same panic he’d buried seventeen years earlier came roaring back.
He wasn’t just losing work — he was reliving the helplessness he’d sworn to out-run.
For many high-functioners, grief disguises itself as control.
I explored this pattern in Toxic Stoicism Isn’t Strength: how our obsession with “calm” and “composure” becomes emotional dehydration.
Opal and Jake both lived that lie—until their nervous systems called it due.
That’s how unprocessed grief works.
It doesn’t disappear.
It waits — until something in the present vibrates at the same frequency as what you never named.
For leaders, that often means the past resurfaces right when others are looking to you for stability.
How to Honor the Grief Without Letting It Eat You Alive
Grief doesn’t need to be managed like a crisis—it needs to be witnessed.
When you stop fighting the feeling, it stops needing to scream.
This is what I meant in Moving Through Grief: Heal, Lead, and Find Solid Ground—grief isn’t regression; it’s the initiation that purifies leadership.
Here’s where to start.
1. Simplify Self-Care to What Actually Soothes
Forget the influencer rituals and twelve-step “healing plans.”
Get a sheet of paper and name five simple things that make you feel good and don’t hurt you or anyone else.
Then do them—slowly, deliberately.
Maybe it’s walking outside, baking, lighting a candle, or yes—eating the ice-cream.
Tiny pleasures can open the same emotional doors grand gestures never reach.
2. Stop Looking for Comfort From the Emotionally Unavailable
If someone has a master’s degree in avoidance, they can’t hold space for your pain.
They’ll minimize, spiritualize, or change the subject.
Protect your energy.
Share with people who can stay present, not those who need you to shrink so they can feel calm.
3. Drop the Performance of Invincibility
Your intellect, discipline, and resilience are gifts—but none of them make you immune to being human.
You don’t think your way out of grief; you breathe your way through it.
Let the body feel what the mind tried to rationalize away.
Tears aren’t weakness—they’re release valves.
4. Remember What This Is—and Isn’t
This isn’t about forced reconciliation or pretending forgiveness equals closure.
Forgiveness is its own mountain; you’ll climb it when you’re ready.
Right now, this is about honoring the parts of you that were gas-lit into silence by emotionally unavailable people.
Acknowledging that, for you, this time of year might not be cozy or magical—and that’s okay.
You don’t owe anyone forced joy.
You owe yourself truth, gentleness, and a place to set down what’s heavy.
Grief Is Good, Just in a Way You’ve Never Known
Grief isn’t punishment; it’s purification.
It scrapes away what was pretending to be strength so real capacity can grow.
For many of us—especially the high-functioning and hurting—the old rule was simple: as long as no one sees you struggle, you’re fine.
But invisibility isn’t healing; it’s erosion.
Maybe this is the season where you stop performing stability and start practicing honesty.
Let the ache be evidence that your heart still works.
Let the tears be proof you’re not numb anymore.
And if you’re the kind of leader who’s spent a lifetime holding everyone else together, consider this: maybe grief is finally holding you—so you can rest, recalibrate, and rise clearer than before.
Softness isn’t surrender—it’s recalibration.
If you’ve forgotten how to trust gentleness, revisit Why You Stopped Trusting Softness; it unpacks how tenderness, once weaponized, can become safe again.
If you’re ready to keep leading without abandoning yourself, I’m here to walk with you.
→ Explore working together
Because grief doesn’t end your leadership.
It refines it.
And the quiet that follows?
That’s not emptiness.
That’s peace finally finding its way home.
