The Bravest Question We Almost Never Ask

She said it so casually.

We were deep into a coaching conversation, talking through her workload, her calendar, and her coaching business decisions.

She was quite overwhelmed, but doing that thing so many women do: staying composed, upbeat even, listing the problems she thought she “should” bring to the call.

And then, almost as an afterthought, she said, “And then there are the holidays.”

It slipped out of her mouth, and she swept it away so fast, you’d think it never happened.

But I saw it.
I felt it.

There was a tiny shift in her face, a wave that washed over her so quickly it might have been missed if I had blinked.

A wave of resignation.

A look I’ve seen in more women than I can count.
A look I have seen in my own mirrored reflection many times.

The look of someone who believes she has no options.
No say.
No room for what she wants.

A look that says,
“This is just how it is. And I don’t get to choose.”

It is a quiet kind of heartbreak, the way women dismiss their own truth before the world even has a chance to.

We wrapped up that session, finishing the work we had started. But we both knew where we needed to go next time. We both heard the sentence she tried to throw away. We put it as a placeholder for our next session.

So when she came back the following week, we opened the door she had tried so hard to keep shut.

We talked about the holidays.
All of it.

She listed everything already planned:
the gift exchange she was hosting,
the meal she had promised her father,
the day her sister and brother-in-law were flying in,
the presents that her teenager and college freshman were looking forward to,
the traditions she felt she “had” to maintain.

Every detail carried the weight of obligation.
Every plan was about someone else.

So I asked her the question that changes everything.
One most women never hear.
A question most women never think to ask themselves.

“What do you most want?”

She looked at me, a bit confused.
Perhaps it came across as if I were speaking in another language.

I asked again.

She kept reciting the list of things she had to do, the expectations she had absorbed, the roles she felt she needed to play.

But that’s not what I asked.
I wasn’t asking about her calendar or her responsibilities.

I was asking about her.

And then, after a long pause, she whispered it.

“Just the four of us in our pjs.”

Her face softened and her eyes brightened.
I even detected a slight sparkle, like light finally reaching a dim room.

In that moment, she remembered herself.

She remembered the holiday during COVID, when everything was suspended, no events to shuttle between, no expectations pulling her in ten directions.

Just the four of them.
A slow day.
A quiet house.
Warmth.
Ease.
Peace.
Connection.

She remembered how good that day felt in her body.
And she let herself feel this truth.

For a moment in our session, she didn’t rush to dismiss the memory that brought her so much joy.
She didn’t bury it under everyone else’s needs and didn’t swallow it like she had swallowed her own desires for decades.

She let it exist.

The smallest act of bravery a woman can make is letting her own truth into the room.

Just naming what she wants.

It’s not just performing perfect holidays.
Or hosting, shopping, and wrapping because everyone expects it.
And not just always being the emotional & support engine for two generations (aging parents and launching kiddos).

Just the four of us.

That was her truth.

A simple awareness and a profound shift.

And that’s where I’ll leave you today.

Because this is the heart of the story.
The moment everything starts to crack open.
When she remembers she has a voice.
And realizes there might be a chair at the table for her, if she’s willing to reach for it.

Next week, in Part Two, I’ll share what happened next:
The tears and the memory that unlocked everything.
The chair she finally claimed, and the surprising way peace replaced obligation.

You won’t want to miss it.

With immense appreciation & gratitude. Always.