47. The Mistake of Chasing Certainty
I used to think clarity came before action.
That if I just thought a little longer, asked a few more questions, ran one more scenario… the right move would reveal itself.
Clean. Certain. Obvious.
It rarely did.
What actually happened was slower.
Decisions stretched.
Opportunities cooled.
Energy leaked.
And all of it felt justified. Because I told myself I was being thoughtful.
But I wasn’t being thoughtful.
I was chasing certainty.
And certainty is seductive.
It makes you feel responsible. Disciplined. In control.
But in most real-world decisions, especially in leadership and finance, certainty is a mirage.
There are too many variables.
The information is incomplete.
The future doesn’t cooperate.
So waiting for certainty doesn’t reduce risk.
It just delays movement.
I started noticing something uncomfortable.
The leaders who moved fastest weren’t reckless.
They just had a different relationship with uncertainty.
They didn’t wait for 100 percent confidence.
They moved at 60 or 70.
And they adjusted quickly after.
While others were still analyzing, they were already learning.
That’s the real shift.
Clarity doesn’t come before action.
It comes from it.
You see it in investing all the time.
The biggest gains rarely come from perfectly timed decisions. They come from being in motion while others hesitate.
Time in the market, not timing the market.
Same principle. Different context.
So I had to reframe the way I think about decisions.
Instead of asking, “Am I certain this is right?”
I ask, “Is this directionally correct, and can I afford to learn by moving?”
That question changes everything.
Because it lowers the barrier just enough to act, without ignoring risk.
Here’s what I’m practicing now.
When I feel myself overthinking a decision, I set a threshold.
What would make this 70 percent clear?
Not perfect. Just sufficient.
Then I decide.
And more importantly, I decide how I’ll adjust if I’m wrong.
That second part matters.
Because confidence doesn’t come from being right every time.
It comes from knowing you can course-correct quickly.
Try this the next time you feel stuck.
Ask yourself:
“Am I actually reducing risk… or just delaying discomfort?”
Be honest with the answer.
Then take one step.
Not a leap. Just a step.
Because in most cases, movement creates more clarity than thinking ever will.
And if you’re in the middle of a decision right now, I’d be interested to hear how you’re approaching it.
Are you waiting for certainty… or moving with intent?
— Jonathan
P.S. Waiting for certainty can feel responsible. Moving with clarity builds momentum. If you’ve been sitting on a decision longer than you’d like, a simple conversation can help you see what’s enough to move. Reach out to me - I’ll guide you.
Disclaimer: This newsletter is intended for general informational and reflective purposes only. It does not constitute financial, legal, or professional advice. Please consider your own circumstances and consult an appropriate professional before making decisions.
