If you’re a capable, experienced professional, planning probably feels like the obvious place to start.
It’s how you’ve been trained.
It’s how you’ve survived.
It’s how you’ve been rewarded.
When something matters, you get organized. You clarify goals. You think through risks. You try to anticipate what might go wrong.
That instinct didn’t come out of nowhere.
You got good at it because it was an essential survival skill.
The Operator at Work
This is the part of you that wants to know:
What does this actually mean?
What does success look like?
Who decides?
What’s the timeline?
What are the risks?
What might this break?
It wants clarity before motion.
And in most corporate environments, that makes sense.
You’re responsible for not breaking things. For not surprising anyone. For making sure the right people are looped in. For avoiding the dreaded “how did we not see this coming?”
The Operator exists to keep the system running smoothly.
It’s not the villain here.
Where Things Get Tricky
This same instinct often shows up when people start thinking about business creation or entrepreneurship.
And that’s where things quietly stall.
Because now you’re trying to plan something that doesn’t exist yet.
You’re asking execution questions before there’s anything real to execute on.
So you spin:
- You overthink and never move.
- Or you prematurely lock onto something just to relieve the discomfort.
What would I even do?
How would I make money?
What’s the model?
Is this viable?
What’s the ROI?
You think this will calm you down—your brain and your nervous system, more specifically.
Instead, it usually ramps things up.
There’s a reason for that.
Researchers who study scarcity talk about how pressure narrows attention (I unpacked this here). When something feels uncertain or risky, the mind grabs for control. It shortens the horizon. It reaches for tools that promise relief now, even if they’re not suited to the situation.
Planning feels like relief.
But relief isn’t the same thing as clarity.
A Subtle but Costly Mismatch
Planning works best when the terrain is known.
When the variables are mostly understood.
When the job is optimization, not discovery.
But early-stage business creation isn’t that.
It’s ambiguous.
Non-linear.
Full of partial information.
Trying to force certainty too early often leads to one of two outcomes:
Neither is great.
This Is the Part No One Taught You
Most corporate careers train Operator mode relentlessly.
Weekly meetings.
Status updates.
Quarterly business reviews.
Endless “what about?” questions.
Very little time is spent learning how to explore without a plan.
So when you hit a moment that requires exploration, your nervous system reaches for the only tool it knows.
Planning.
Not because it’s wrong—but because it’s familiar.
Good Tool, Wrong Moment
If you’ve been stuck here, nothing has gone wrong.
This doesn’t mean you’re not an entrepreneur—or that you’re not capable of becoming one.
You’re using the wrong mode too early.
Planning isn’t bad.
It’s just out of sequence.
There’s another mode that needs to come first.
I’ll talk about that next.
Helping you make room for something new,
Pierre
Certified Professional Coach
P.S. If this stirred a mix of relief and discomfort, that’s normal. You’re starting to notice the difference between executing work and figuring out what work is worth doing.
Photo by Kaleidico on Unsplash
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