What You Think Is Strategy Is Actually Guesswork
What You Think Is Strategy Is Actually Guesswork
An honest approach to using intelligent tools to grow your membership — without outsourcing your authority.
You’re refining the copy.
You’re tweaking the onboarding.
You’re adjusting the price (again).
You’ve got a dozen tabs open, a funnel half-built, and a color-coded plan that should work.
You tell yourself this is strategy.
But if we’re being honest?
This is guessing.
Educated guessing. Pattern-based guessing. Intuitive, slightly sweaty, “I-hope-this-works” guessing.
And it’s not that you’re doing it wrong — it’s that most people are.
Because strategy — real strategy — doesn’t live in what you feel.
It lives in what you know.
And right now, you might be building on assumptions dressed up as certainty.
Your business isn’t fragile.
But your clarity might be.
That’s why your launch works… once.
That’s why your community is “engaged”… until it isn’t.
That’s why your best members cancel with no feedback, while others quietly stay — and you can’t explain either one.
You’ve done the work.
You’ve earned the trust.
You’ve built something real.
But now?
It’s time to stop guessing — and start listening to the systems you’ve already built.
Because your data isn’t abstract.
It’s personal.
And it’s trying to show you what your emotions won’t admit.
Guesswork sounds like:
“This content should land with them.”
“I think this bonus will help reduce churn.”
“Let’s drop the price and see what happens.”
“I just need to market it harder.”
It sounds like effort.
But it’s effort without direction.
Which makes it expensive.
Because no matter how heartfelt your intentions are,
you can’t scale something you don’t understand.
Strategy is rooted in evidence — not over-functioning.
If you’re scaling a hybrid membership or subscription model, your real job isn’t to predict.
It’s to observe.
Look at:
What people actually use
What triggers retention — or cancellation
When your engagement peaks
Where people pause in the onboarding
How your best-fit members behave differently than your high-maintenance ones
This is intelligence — and it’s already in your hands.
But it’s easy to ignore when you’re emotionally invested in a feature you love, a message you worked hard on, or a delivery style you used to enjoy.
So instead of shifting, you double down.
You “try harder.”
You guess louder.
That’s not leadership.
That’s survival.
The dangerous thing about guessing?
It feels like working.
It keeps you busy.
It keeps your calendar full.
It gives you the illusion of strategy, when you’re actually just avoiding the real decisions.
Should this offer even exist?
Should this tier be eliminated?
Should this be simpler — and braver — than I’m currently allowing?
You don’t answer those questions with intuition alone.
You answer them with information.
So how do you make the shift?
Start by asking:
What’s actually being used — and what’s performative?
What would I remove if I weren’t emotionally attached to it?
Where is my marketing disconnected from the experience?
What are my members doing that contradicts what I believe about them?
Then — use your tools.
You don’t need to become a data analyst.
You just need to build a habit of checking reality against your assumptions.
Check your churn.
Check your usage.
Check your engagement loops.
Check what members say they want… versus what they actually do when they get it.
You’ll be surprised by what you learn.
And relieved by what you can let go.
Final thought
You’re not underqualified.
You’re not behind.
You’re not “doing it wrong.”
You’re just building on a shaky strategy — because no one ever showed you how to ground it in evidence.
But now you know.
You don’t need to guess.
You don’t need to prove.
You don’t need to build faster than you can refine.
You just need to trust the intelligence inside your business — and act on it.
Because what you call a “strategy problem” is often just an uncalibrated instinct.
The answers are already there.
And they’ve been waiting for you to stop guessing long enough to see them.
