11 Questions That Can Rewrite Your Story (In Times of Change)
Change begins when you ask the right question.
A friend of mine, Marek, once said something to me years ago that has never left me:
“The biggest shifts in my life didn’t come from answers. They came from better questions.”
Not clever ones. Not tidy ones.
But the kind that make you fall silent for a minute.
Like:
What have I been avoiding?
What would I do if I wasn’t afraid?
What story am I in—and who’s the author?
We’re often taught to think of change like flipping a switch.
But in my experience, change doesn’t come with certainty.
It comes through questions.
The right question.
The question that, when you’re still enough to hear it, changes everything.
The moment of clarity never happens before.
It happens in the stillness.
It happens with the question.
What I Mean by “Questions”
By questions, I don’t mean the “how-to” kind.
The “what-to-do-next” kind.
I mean the kind that alters your relationship to life.
The kind that cuts you off mid-thought.
The kind that never want a hasty answer.
The kind that open a small space between the life you know and the life you’re here to live.
A real question is a mirror.
Not of what you know—
But of what you’re willing to see.
The Questions the World Gives Us
The world gives us questions too.
But they’re flimsy. Procedural. Extractive.
How do you make more?
How do you get six figures?
What’s your five-year plan?
How can you be more productive?
They sound important. Strategic.
But they rarely touch the soul.
They miss the fact that people don’t change because they’re more optimized.
They change because they’re seen.
Because they get honest.
Because something inside of them finally says, “I can’t keep living like this.”
A Mirror from Someone Else’s Life
Years ago, I read an article about a hospice nurse who kept a journal of confessions.
The most frequent one?
“I wish I had lived a life true to myself—not the life others expected of me.”
No one said,
“I wish I would have worked harder.”
“I wish I would have answered more emails faster.”
What they regretted wasn’t that they failed.
They regretted that they never asked the right questions.
They hadn’t asked,
Whose life am I living?
long enough.
And by the time they did, it was too late to live it differently.
When I Stopped Asking the Right Question
I remember a season of my life when it looked like it was clicking on all cylinders.
Coaching was going well.
My calendar was full.
I was checking all the right boxes.
But on the inside, something was tightening.
I wasn’t asking why I was so tired.
Why I felt constricted in my own life.
Why, when I said “yes” to so many things, I felt like I was saying “no” to myself.
And when I finally slowed down long enough to listen,
the question that came through was not strategic.
It was spiritual:
“What are you here to say that only you can say?”
The question didn’t change anything overnight.
But it started the undoing.
And for me, undoing is the beginning of change.
A Pattern I See Again and Again
In every coaching client I work with, there comes a moment when the shift begins.
It’s not when they get the answer.
It’s when they sit with a deeper question long enough for it to settle.
What part of me have I been protecting?
What’s the cost of staying here?
If I trusted myself more, what would I walk away from?
The breakthrough always comes after the question.
Not because it “fixes” it—
But because it names what matters.
🧭 11 Questions to Rewrite Your Story
So here are eleven questions I use a lot—
in my coaching and in my own becoming.
Let each one land. Take time. One might open a door.
What is the outcome you’re actually longing for?
What scares you about going after it?
What is the deeper learning in this current moment?
What are you pretending not to know?
What does success really look like—for you?
What belief might no longer be true?
If you say yes to this, what are you saying no to?
What’s the next small move that feels honest?
What is the real challenge—not the one on the surface?
What do people consistently appreciate in you?
What would you do if failure wasn’t an option?
Pick one. Sit with it.
Not to answer it, but to let it rewrite you.
A Small Practice That Can Change Everything
So here’s the invitation:
Don’t rush to figure your life out.
Sit with it.
Ask into it.
Let it unfold.
Write the question on a sticky note.
Put it in your journal.
Go to therapy with it.
Ask it before bed.
Live with it long enough to let it change something.
Because when you ask the right question—and stay long enough to hear the answer—
the question quietly arranges you gently, but permanently.
Full Circle
When Marek said,
“The biggest shifts in my life didn’t come from answers. They came from better questions,”
what I think he meant was this:
Change doesn’t come when you find the right path.
It comes when you stop long enough to listen to what’s already true.
So ask something real.
Then wait.
Stay long enough to hear the answer behind the answer.
That’s where your new story begins.
✉️ The Invitation
If you’re in a season of change and want support naming the question that matters most—I’d love to walk with you.
👉 [Book a free coaching session here.]
Let’s ask better questions.
And write a future that fits who you’re becoming.
Each of these questions feels like a flutter of possibility inside me, Andy. Thank you so much. This unconventional kind of deep exploration meets me at exactly the right time in my evolution. I'm so grateful to you. Thank you sincerely.