Issue #44 - January 20th, 2026
Written by Michael Gillespie
In this issue:
Perspective: Most membership advice is designed for starting - not sustaining. It all works…until it doesn’t.
Insight: After year two, tactics age out and operational maturity becomes the real growth lever: Operational truths you should know.
Outlook: Operational strength is rarely talked about: Why it’s time to stop chasing plays and start building durable systems.
QUOTE OF THE WEEK
“Early tactics create motion. Mature operations create longevity.”
There’s this moment that most membership operators hit…
Usually somewhere around year two, where the typical “advice” starts to feel…thin.
Not wrong. Just incomplete.
The playbooks that helped you get traction - launch sequences, posting cadences, funnel tweaks, urgency, new perks - can still create bursts of movement. But they stop creating the kind of stability you’re actually after.
Even if nobody says this out loud, it can make you doubt what you’re doing…
You’ll start wondering if you’ve lost your edge…if the market moved on.
If your offer isn’t as good as it used to be.
I get it - I’ve been there.
But in reality, you’re entering the phase where tactics simply stop being the point.
This is the part of the membership journey that just doesn’t get talked about enough:
The shift from starting to sustaining.
It’s a shift that’s often missed. And this is the precise moment where the future of your business is determined.
Let’s dive in.
PERSPECTIVE
After Year Two, The Advice Stops Fitting.
Most membership advice is written for the early game…when you’re still proving demand, building an audience, and finding your rhythm.
In that stage, your biggest constraint is often attention:
getting people to notice you
getting them to understand the offer
getting enough momentum to feel real
So the advice makes sense: ship fast, launch often, tighten the pitch, add urgency, create the spikes, stay visible.
But after year two, the game changes.
Your audience has largely heard the message
Your offer has been validated
Your members have formed expectations
Your delivery rhythm has become a lived experience, not a promise.
Now your biggest constraint is no longer attention.
It’s operations.
It’s the ability to deliver consistent value without burning out. To keep the membership feeling alive without constantly reinventing it. To retain members through seasons where novelty wears off. To manage complexity before it quietly becomes overhead.
This is why early tactics age out.
Many memberships begin and die running tactics instead of operations.
Why?
Because tactics are intriguing and exciting. But operations are boring.
Here’s the thing: Boring activities keep memberships alive and running.
INSIGHT
The Mature Operator’s Job Is Different.
Once you’re past the early stage, you’re no longer “trying to get membership working.”
You’re trying to get membership enduring.
That requires a different orientation - less about growth hacks, more about business architecture.
Here are the core truths mature operators internalize:
You can’t sprint forever
Early momentum is often powered by intensity.
Mature momentum is powered by rhythm.
If your membership still depends on bursts of effort, it’s fragile…even if it looks healthy.Retention becomes your real acquisition channel
In the early game, you grow by reach.
In the mature game, you grow by trust.
A stable membership recruits through its members: word of mouth, referrals, reputation, and quiet credibility.Clarity becomes more valuable than novelty
New perks can create movement.
But clarity creates loyalty.
Mature members don’t stay because you surprise them. They stay because the membership reliably delivers what it promised.Complexity is the silent killer
Mature memberships often accumulate “barnacles”: extra offers, extratiers, extra perks, extra systems. And each one adds operational drag.
The best operators don’t just build…they prune.Judgment replaces frameworks
Early on, frameworks are helpful because you don’t yet know what matters.
Later, your advantage is discernment:what to ignore
what to double down on
what to simplify
what to stop doing entirely
That’s what maturity looks like.
Not more tactics. Better decisions. Better operations.
OUTLOOK
Sustaining Is the Real Flex.
If the early playbooks feel less effective, that may be a sign you’re doing something right.
It likely means you’ve moved into the phase where outcomes are shaped less by clever moves and more by consistency, care, and operational strength.
And that phase is not a downgrade. It’s the business. A business that can live for years into the future.
This is where membership becomes what it was always meant to be: a durable model built on trust, rhythm, and stewardship.
This year, my focus will be on inspiring you to build more than just a membership: an operationalized business that’s powered by membership.
The difference sounds subtle, but the outcomes are wildly different - and one of them is life-changing.
As you look at your membership right now, here’s the question worth asking:
Are you still operating with a year-one playbook - or designing for year ten?
Think about it.
