“‘Someday I’m going to write a book.”
She said it the way people say things they’ve said a hundred times. Lightly. With a laugh. A glass of wine in her hand while the band played two tables over.
I asked her why not now. She laughed it off.
“No, no. Someday.”
I tried again, gently…what if you just started something small? What if you shared a piece with someone you trusted?
Every time, she deflected. Laughed it off. And moved her writing dream safely back to someday. Where it couldn’t be touched. Couldn’t fail. And couldn’t be taken from her.
Is it too late to want more — not someday, but now?
No. But most women don’t ask the question that plainly.
They tuck it somewhere safer first. Behind a laugh. Behind “someday.” Behind whatever keeps it from being tested or taken away.
The Things She Set Aside
She’s in her late fifties, recently retired.
Sharp. Funny. Has the kind of warmth that makes you feel, within minutes, like you’ve known her for years.
At some point she told me she’d always loved English — that writing had lit her up. She moved past it quickly though, like it didn’t mean anything.
I asked if she’d thought about pursuing it. Her face changed.
Yeah. She’d wanted to, actually.
But her parents had told her it wasn’t a real job. That there was no money in it. So she’d set that dream down and kept walking.
Later, a friend had read something she wrote and told her it wasn’t good enough to get published. So she stopped sharing it. Eventually she stopped writing much at all.
When she told me what she’d done before retiring — “just” a mom, “just” an executive assistant — I pushed back a little.
I asked her if she knew how much skill it takes to organize, juggle, and hold everything together for everyone, for years.
She shrugged. Smiled. Moved on. She just couldn’t let it land.
By the end of the night, she grabbed my hand and said “You’re really good at this.”
What she meant was: you made me feel seen.
What Regret Is Actually Pointing At
Here’s the part most of us get wrong about regret.
We think it means we failed, or chose badly, or wasted something.
So we push it down. Laugh it off.
File it under “someday” where it’s safe. Where it can’t be touched, can’t fail, and can’t be taken away.
But regret isn’t proof you got it wrong. It’s proof you know what matters to you.
Every regret like hers has two sides.
One is the ache. The writing she gave up, the words she stopped trusting herself to put down on paper.
The ache is real. And underneath it, there’s something else — the other side of it. A craving, a yearning, something that hasn’t actually gone anywhere.
This is something I see constantly in my work as a life transitions coach for women.
The regret rarely arrives as a desire to start over. It arrives small — a wish, a flicker, a thing she mentions and then moves past quickly.
As though saying it out loud costs her something.
So, Is It Too Late to Want More?
No. But it’s worth being honest about what “more” usually means here, because it’s almost never the dramatic version.
She didn’t need to quit everything and write a novel.
When I gently pushed — what if you just started something small? What if you shared a piece with someone you trusted? — I wasn’t suggesting she upend her life.
I was asking if she’d let herself have a small piece of it, now, instead of postponing all of it to someday.
That’s usually the real question underneath “is it too late.” Not is it too late to become someone else, but is it too late to let the woman who already loved that thing have a little bit more of it.
It isn’t. It’s never actually too late for that.
Whose Voice Have You Been Believing?
Her parents told her writing wasn’t a real career. A friend told her she’d never get published.
Neither of those things were ever actually true — they were just said with enough certainty, enough times, that she stopped checking.
That’s a pattern I see again and again…
A woman quietly accepts something someone else said about her, decades ago, as fact.
She talks herself out of what she already knows — not because the evidence changed, but because it became easier to agree than to keep arguing for herself.
If you’ve spent years carrying a version of yourself someone else handed you, finding your way back to who you actually are usually starts smaller than people expect.
Not a leap. Just one small piece, reclaimed.
Where This Leaves You
She’s not going to become a bestselling novelist overnight.
She’s also not entirely sure yet what comes next — the journal she starts, the piece of writing she finally finishes, the door she finally opens.
But something shifted between the someday at the start of the night and the moment she said you’re really good at this.
She let her regret talk, instead of laughing her way past it.
Your regrets aren’t proof you got it wrong. They’re proof you know what still matters to you.
Somewhere underneath the years of putting everyone else first, that part of you hasn’t gone anywhere. . She’s just been waiting for you to stop sending her to someday.
If you’ve got a regret of your own sitting somewhere quiet — the thing you tell yourself you’ll get to someday — my free guide It’s Not Too Late: What Your Regrets Are Really Trying to Tell You walks you through what to do with it.
Not a plan. Not a life overhaul.
Just a way to start listening to what it’s actually pointing you towards.
Kerry xo