If you’ve ever asked yourself why do I keep second-guessing myself, you’re probably not lacking information.
You’re not confused about the facts.
Somewhere underneath all the deliberating, there’s usually a quiet knowing that’s been there for a while.
The harder question is why you keep talking yourself out of it.
The knowing that arrives before the decision
There was a stretch of time when I cried in my car before work.
Not every day. But enough that it became a bit of a pattern.
I’d sit in the parking lot, try and pull myself together, and then brace myself for whatever was waiting on the other side of that door.
My boss was negative and unpredictable. And completely unaware of the effect his energy had on everyone around him.
What made it harder was everything else I was carrying.
A single mom with a young son. Aging parents who needed me more and more.
I didn’t feel like I had the luxury of walking away from a steady paycheque.
So I stayed. And I braced.
And I cried in my car when it got to be too much.
The whispers of discontent had been there for a while, but I kept talking myself out of them.
Then one afternoon, the hospital called about my dad.
I stepped outside into the cold November air to take the call privately.
When I turned back to the door, it was locked.
And there on the other side of the glass was my boss...yelling at me.
I was completely shocked. Angry.
And then something in me went still. Not calm exactly. Just clear.
When he finally let me back in, I walked past him and straight to my desk. Turned off my computer. Picked up my purse. And left without saying a word.
My body knew before my mind caught up.
It’s not just work
That story is about a job. But the pattern shows up everywhere.
It’s there in a:
- Relationship where something has felt off for longer than you want to admit, but you keep telling yourself you’re probably overreacting.
- Friendship that drains you every single time, but she needs you, and you don’t want to be the one who pulls away.
- Living situation you’ve outgrown.
- Role you’ve been playing for years that no longer fits.
- Decision you’ve been circling for months because acting on it means someone else’s life gets disrupted.
It’s any situation where you already have a sense of what’s true. But you keep finding reasons to wait a little longer.
What I hear most often from the women I work with is this:
I already knew the answer. I just needed permission to trust it.
Why we keep second-guessing ourselves
Second-guessing yourself isn’t a character flaw.
It’s what happens when you’ve spent years being the one who holds everything together.
When your choices affect people you love, their imagined reactions can start to drown out your own. When the stakes feel high, even a clear knowing can feel too risky to act on.
And when you’ve been taught — directly or just by watching — that your needs come last, you get very good at talking yourself out of things.
The waiting feels like being careful. Like being fair.
Like not wanting to make a big deal out of things.
But underneath all that reasonableness, something is still waiting to be heard.
What changes when you stop overriding yourself
Over the years what I’ve thought about the most isn’t what I did that day.
It’s how long I already knew.
The whispers were there long before the wall came crashing down.
The knowing was there…I just kept overriding it.
Waiting for circumstances to make the decision feel easier.
Safer. More certain.
Certainty rarely arrives before a decision. It usually shows up after.
And the longer you wait for it, the longer that quiet knowing sits there…patient, steady, and a little bit tired of being ignored.
The shift isn’t dramatic.
It’s just learning to pause at the moment you’re about to explain yourself out of something again.
And asking: what did I know before I started talking myself out of it?
That’s usually where the answer already is.
If this resonated, my free guide How to Stop Second-Guessing Yourself is a good next step.
It’s a short, practical decision-making tool for women who keep overriding what they already know — including a simple three-step process to help you hear yourself again.
Kerry xo