Welcome back to Grace Over Guilt. I’m Dan Kaufman.

If you are reading this right after Christmas, I hope it was meaningful, whatever “meaningful” looked like for you this year.

And I want to say something up front that I wish someone had said to me in my first holiday season after everything changed:

Not every Christmas feels like Christmas.

Sometimes it feels like survival wrapped in tinsel.

Sometimes it feels like showing up with a smile while your chest is heavy.

Sometimes it feels like grief sitting in the living room with the lights on.

Sometimes it feels like you are watching other people live the life you used to have.

So today I want to talk about something a lot of us deal with this time of year, whether we admit it or not:

Holidays in transition.

Holidays when everything has changed.

Holidays when the traditions do not fit anymore.

Holidays when the people who used to be there are not.

Holidays when you are not sure what you are supposed to do with your hands, your heart, or your hope.

This hit me hard after I got out of jail in 2022, and it is still something I navigate today.

Because transitions do not end when the calendar flips.

Some transitions last years.

And part of healing is learning how to move through them honestly.

Not pretending.

Not spiraling.

Not forcing joy like it is a duty.

But also not letting grief steal every remaining inch of meaning.

There is a way to hold both.

That is what this is about.

Before the transition: the Christmases I took for granted

Christmas used to be one of my favorite times of year.

I had a family.

A wife.

Two daughters.

We had traditions. Not perfect traditions, but ours.

The way we decorated the tree.

The meals we made.

The presents we wrapped.

The rhythm of Christmas morning.

The feeling of being together, being a unit, being home.

When you have that, you do not analyze it. It is just what Christmas is.

It becomes the background of your life.

It is the assumption you build the season around.

It is the part of your story that feels stable.

And stability is invisible until it is gone.

That is one of the painful truths of loss.

You do not fully understand what something meant until you do not have it anymore.

Then you realize how many of your emotions were attached to ordinary things.

A specific ornament.

A silly tradition.

A certain recipe.

The sound of your kids in the other room.

The casual intimacy of being known.

When I look back now, I can see how much I took for granted.

Not because I was ungrateful, but because I assumed the structure would stay.

I assumed the “togetherness” would keep happening because it always had.

That assumption is a form of innocence.

You do not know it is innocence until it is shattered.

The first Christmas after jail and divorce: brutal and quiet

My first Christmas after jail, after the divorce, was brutal.

Not loud brutal, but quiet brutal.

Quiet brutal is sometimes worse because there is no explosion.

There is just a constant ache that you cannot distract yourself from.

I was at my parents’ house.

They tried to make it nice.

They put up decorations.

They made food.

They did their best.

And I was grateful.

But I was not with my daughters.

I was not in my home.

I was not the dad waking up early to see their faces when they came downstairs.

I was not the husband handing presents to my wife.

I was a grown man in his parents’ guest room, trying to pretend everything was okay when nothing was okay.

There is a specific kind of pain that happens when your life is still moving but the identity you used to live inside is gone.

You feel like you are watching someone else’s life.

Like you are an observer at a holiday that does not really include you, even if people are kind and welcoming.

I was there physically.

But emotionally I was somewhere else.

Somewhere between grief and numbness.

That is what holidays in transition feel like.

You are present, but not really.

You go through the motions, but the meaning feels missing.

The old traditions feel hollow because the context that gave them meaning has changed.

And if you have never experienced that, you might think: “Just make new traditions.”

But the grief comes first.

Before you can build new meaning, you have to admit what you lost.

Transition holidays: why they are so disorienting

Here is what makes transition holidays uniquely disorienting:

They are layered.

You are not just grieving what you lost.

You are also fighting the cultural expectation to be happy.

You are also watching other people enjoy what you wish you had.

You are also dealing with logistics.

Where do I go?

Who do I see?

Who do I not see?

Do I text them?

Do I call?

Do I wait?

Do I show up?

Do I stay home?

Do I pretend?

Do I cry?

Do I avoid?

Do I drink?

Do I overwork?

Do I scroll?

The holidays do not just bring emotion.

They bring decision points.

And decision points are exhausting when you are already depleted.

You are also facing memories.

Smells.

Songs.

Photos.

Old traditions that are still happening somewhere, just without you.

All of that makes the season heavy.

And if you do not name it, it can turn into shame.

You start thinking you are doing Christmas wrong.

You start thinking you are broken because you cannot “get in the spirit.”

But you are not broken.

You are transitioning.

And transition has a cost.

The pressure to perform joy is real, and it can be cruel

I want to talk about the pressure for a moment.

Because a lot of people suffer in silence during the holidays, not because they are sad, but because they feel guilty for being sad.

They feel like sadness is disallowed.

Like the season requires cheer.

So they put on a performance.

They smile.

They laugh.

They say the right things.

And then they go home and crash.

Or they go to the bathroom and cry.

Or they lie awake at night with their mind racing.

This is especially hard if you are newly divorced, newly sober, newly grieving, newly estranged, newly bankrupt, newly unemployed, newly out of jail, newly diagnosed, newly alone.

When you are new to loss, the holidays feel like a spotlight.

You are not just experiencing pain.

You are experiencing pain in public.

So let me give you permission, if you need it:

You do not have to perform joy to be worthy of love.

You do not have to pretend your life did not change.

You do not have to force cheer to be “spiritual.”

Sometimes the most honest thing you can do is admit: this is hard.

Admitting it is hard does not mean you are ungrateful.

It means you are honest.

What I learned about holidays in transition

After a few Christmases since everything fell apart, I have learned a few things.

I am still learning, but these truths have helped me not drown in the season.

1) It is okay to grieve

The Christmas you used to have is gone.

That is a loss.

Losses deserve to be mourned.

You do not have to pretend to be cheerful.

You do not have to force joy you do not feel.

Grief is not a failure of faith.

Grief is love with nowhere to go.

If you lost your family structure, your home, your role, your sense of belonging, your confidence, your identity, your stability, you are allowed to grieve.

Grief is not weakness.

It is the cost of meaning.

The goal is not to eliminate grief.

The goal is to make room for it without letting it control everything.

2) The old traditions might not fit anymore, and that is not betrayal

Some people try to recreate the old holiday exactly.

Same meal. Same schedule. Same rituals.

Sometimes that helps.

Sometimes it hurts.

If the people and context that made the tradition meaningful are not there, the tradition can feel like an echo.

It can feel like a reminder of what you lost.

If that is you, hear this:

It is okay to let some traditions go.

It is okay to change things.

It is okay to build new rituals.

That is not betrayal of the past.

It is acknowledgement of the present.

And acknowledgment is where healing begins.

3) You can choose “good enough” instead of “perfect”

This was a big lesson for me, especially as someone who likes to fix, plan, and control.

When your holiday is in transition, perfection is often impossible.

Trying to force it creates more pain.

So instead, aim for good enough.

Good enough food.

Good enough connection.

Good enough effort.

Good enough presence.

If the season is hard, your goal is not to create a movie.

Your goal is to survive without losing yourself.

4) Small moments matter more than big scenes

When you cannot have the big picture perfect holiday, focus on small moments of connection.

A genuine conversation.

A shared meal.

A moment of laughter.

A walk.

A kind text.

A simple prayer.

These small things add up.

They become the foundation for new memories.

They also remind you that your life is not over.

It is changing.

5) Gratitude is not automatic, but it is essential

Gratitude and grief can coexist.

They do not cancel each other out.

This was hard for me because I felt like gratitude was supposed to be natural.

But sometimes gratitude is a choice you make on purpose.

I had to consciously choose to be grateful for what I did have:

My parents’ generosity.

A roof over my head.

A warm meal.

The fact that I was free.

The fact that I could still reach out to my daughters, even if the connection was fragile.

Gratitude does not erase pain.

But it keeps pain from becoming your whole identity.

The complicated part: transition can trigger shame

Here is something I did not expect.

The holidays can trigger shame.

Because you see what you used to be.

You see what you used to have.

You see other families.

You see smiles.

You see kids running around.

You see couples holding hands.

And your mind starts comparing.

Comparison is a shame factory.

Especially when your transition includes consequences.

When you know some of the loss was caused by your own choices, the holidays can feel like punishment.

You start thinking: “This is what I deserve.”

That is a dangerous thought.

Accountability matters. Repair matters. Consequences are real.

But shame is not repair.

Shame is paralysis.

So if you feel shame rising in the season, here is a practice that helped me:

Name the shame sentence, then answer it with truth.

Shame says: “You ruined everything.”

Truth says: “I made choices that hurt people, and I am doing the work to repair what I can.”

Shame says: “You do not belong.”

Truth says: “I am in transition. Belonging can be rebuilt.”

Shame says: “This is your forever.”

Truth says: “This is a chapter.”

Sometimes truth is not positive.

Sometimes truth is simply grounded.

And grounded is better than spiraling.

This Christmas: still in transition, still building

This Christmas, I am still in transition.

I am still building.

I am still working on relationships with my daughters.

Texting with my youngest.

Still waiting for my oldest to respond.

If you have ever been in that place, you know the tension.

You do not want to pressure.

You do not want to manipulate.

You do not want to turn your effort into a guilt trip.

But you also do not want to disappear.

You want to communicate: “I am here. I care. I am not giving up.”

That is a delicate line.

So I keep showing up in small ways.

A text.

A check in.

A simple message that does not demand anything.

And I keep doing my internal work, because I have learned something important:

You cannot rebuild connection if you are not becoming safe.

Safety is built through consistency.

Consistency is built through integrity.

Integrity is built through daily choices.

So yes, the holiday is different than what I imagined.

But it is mine.

It is real.

And there is meaning in it.

Not despite the struggle, but because of it.

Every holiday I show up.

Every effort I make to stay connected.

Every moment of genuine gratitude.

Those things matter.

They are building something new.

The holidays you are having now might not be the ones you wanted.

But they can still be meaningful.

They can still be yours.

How to navigate holidays in transition without losing yourself

Let me offer a few practical strategies that helped me. Take what fits and leave the rest.

Make a “minimum viable holiday” plan

If you are overwhelmed, do not plan a perfect holiday.

Plan a survivable one.

Ask yourself:

Examples:

A minimum viable plan is not failure. It is wisdom.

Decide how you will handle memory triggers

Songs, movies, traditions, photos.

They can be beautiful and brutal.

So decide ahead of time.

If a certain movie is going to crush you, do not watch it this year.

If a certain tradition is going to trigger anger, change it.

You are allowed to protect your nervous system.

This is not weakness. It is stewardship.

Give yourself a script for awkward conversations

People will ask questions.

Sometimes they mean well.

Sometimes they are nosy.

Sometimes they are uncomfortable and talk too much.

So have a simple script ready:

You do not owe everyone your full story.

You owe yourself peace.

Focus on one connection, not ten

When you are in transition, your relational capacity may be smaller.

That is normal.

So focus on one safe connection.

One person who sees you.

One person you can be honest with.

One person you can talk to without performing.

That one connection can be the difference between spiraling and surviving.

Let meaning be quiet

A lot of people expect meaning to feel big.

But meaning can be quiet.

Meaning can be sitting with your parents and letting the awkwardness be there.

Meaning can be writing a letter you do not send.

Meaning can be praying even when you feel numb.

Meaning can be choosing to be sober.

Meaning can be choosing to stay alive.

Meaning can be choosing not to hate yourself.

Quiet meaning is still meaning.

If you are in divorce, estrangement, or loss right now

If you are navigating holidays in transition because of divorce, estrangement, death, addiction recovery, legal consequences, or any major change, I see you.

This time of year is hard.

The pressure to be happy and connected when you are struggling is immense.

But you are not alone.

And the holidays you are having now, as imperfect as they are, are part of your story.

They are not the whole story.

There are more chapters ahead.

Let yourself grieve.

Let yourself feel.

Let yourself hope for what is still possible.

Hope does not have to be loud.

It can be as simple as saying: “I will keep going.”

And if you are reading this and you do not feel hopeful, that does not make you a failure.

Sometimes hope is not a feeling. Sometimes it is a decision.

Sometimes it is the choice to take the next right step.

Sometimes it is the choice to stop punishing yourself.

Sometimes it is the choice to accept help.

Sometimes it is the choice to tell the truth.

Sometimes it is the choice to send the text that says, “I am thinking of you,” without demanding a response.

That kind of hope is humble.

And humble hope is powerful.

If the holiday season is exposing the fractures in your life, remember this:

Transition is not the end.

It is the middle.

It is the awkward bridge between what was and what will be.

Bridges do not feel like destinations.

They feel like vulnerability.

But they are how you cross.

So be patient with yourself.

Be honest about your grief.

Be intentional about what you can control.

Let small moments matter.

Choose gratitude when you can.

And do not confuse a hard holiday with a hopeless life.

Grace over guilt.

A deeper framework: how to rebuild holiday meaning when the old meaning is gone

When your life changes, the holidays become a mirror. They reflect what you lost, what you regret, and what you still want. Here are a few deeper ideas that helped me make sense of the season when I felt like I did not fit inside it anymore.

1) Grief is not only about who is missing, it is about who you used to be

I used to think I was grieving people and circumstances. I was. But I was also grieving myself.

I was grieving the version of me who woke up on Christmas morning certain about who he was. I was grieving the version of me who believed his family story was stable. I was grieving the version of me who thought his job was to make everything feel safe.

When that version of you disappears, the holidays can feel like an identity crisis. That is normal.

If you name that you are grieving your old self, you can stop judging yourself for not feeling “festive.” You are not failing the holiday. You are mourning an identity shift.

2) Meaning is not found, it is built

A lot of us talk about finding meaning like it is hidden somewhere, like you just need the right perspective and it will appear.

In my experience, meaning is built. It is built through choices. It is built through presence. It is built through actions that align with your values, even when your emotions are behind.

If you do not feel meaning, do not panic. Ask: what would a meaningful choice look like today?

Meaning often comes later, as a result.

3) Your nervous system needs a plan

Transition is not only emotional. It is physiological. Your body learns patterns. When the patterns break, your body reacts.

That is why the holidays can trigger panic, insomnia, irritability, numbness, or avoidance. It is not only sadness. It is your system bracing for impact.

So give your nervous system a plan:

Planning is not controlling. It is caring.

4) There is a difference between honoring the past and living inside it

Honoring the past can look like lighting a candle. Hanging one ornament. Making one dish. Writing one card. Saying one prayer.

Living inside the past looks like replaying old memories until you cannot breathe.

Honor the past in small ways, then return to the present. Your future needs you here.

5) Transition requires boundaries

This is a big one.

When you are in a fragile season, boundaries are not selfish. They are survival.

Boundaries can sound like:

Boundaries protect your peace. Peace protects your capacity. Capacity protects your relationships.

6) If your holiday is lonely, do not assume you are unlovable

Loneliness is not proof of unworthiness. It is often a consequence of transition, circumstance, and timing.

If you are lonely, your job is not to judge yourself. Your job is to care for yourself.

Call someone. Join something. Serve. Attend. Walk. Write. Pray. Sleep. Eat.

You cannot shame yourself into belonging.

7) Your story is still being written

This is the line I return to when the season feels like a verdict.

This Christmas is not a verdict. It is a chapter.

The holiday you are having now might not be the one you wanted, but it does not have to be meaningless.

You can still show up. You can still rebuild. You can still become safe. You can still love. You can still be loved.

Grace over guilt.