We’re officially wrapping up the Digital CEO Diaries series, and I wanted to end it with one of the most important—and most misunderstood—topics in online business: membership retention.
Because here’s the truth: starting a membership isn’t the hard part.
Keeping people inside it is.
I’ve talked about memberships before (dating myself here—probably 2020 or 2021), and while I do love them, I also have a bit of a love–hate relationship with the model. Not because memberships don’t work—but because most people underestimate what it actually takes to run one well.
Today, we’re breaking down:
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The real reasons members cancel
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Why memberships feel harder to sell than one-time offers
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And the three pillars that actually keep people paying month after month: strategy, accountability, and community
Why Memberships Are Harder Than They Look
On paper, memberships sound amazing.
Set it up once.
Recurring monthly revenue.
Predictable cash flow.
But what people forget is this: a membership isn’t just about getting people in—it’s about keeping them engaged.
Psychologically, an open-ended monthly charge creates more resistance than a one-time payment. In fact, it’s often easier to sell a $200 course than a $25/month membership.
Why?
Because when someone pays a one-time fee, they’re buying a clear outcome.
When someone pays monthly, what they see is an ongoing charge—and all the fear that comes with it:
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“What if I forget about it?”
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“What if I don’t use it?”
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“What if this just drains my bank account?”
So if you’re going to run a membership, you have to constantly reinforce value—not just at the sale, but every single month.
The Two Reasons People Cancel Memberships
This is where clarity matters most.
There are only two core reasons people cancel:
1. They’re Not Using It
The moment someone stops engaging, the question becomes:
“Why am I paying for this?”
This typically happens later—six months in, a year in—when momentum dies off.
2. They Feel Overwhelmed or Behind
This is the big one in the first 30–60 days.
They bought with the best intentions…
They logged in…
Saw everything…
And promptly shut down.
Overwhelm leads to avoidance. Avoidance leads to cancellation.
Your job as the membership owner is to get ahead of both problems.
The Goldilocks Rule: Stop Giving Too Much
This is counterintuitive, especially for coaches.
We want to give everything.
All the trainings.
All the resources.
All the bonuses.
But more content does not equal more value.
Too much content without direction turns your membership into an educational library, not a transformation container.
What people actually need is:
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A clear starting point
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A simple roadmap
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And a quick win early on
Your First 7 Days Matter More Than the First 30
If you want retention, you need momentum—fast.
In Strategy Lab, for example, there’s a very obvious “Start Here” section. The goal is not to overwhelm—it’s to help members win immediately.
Ideally:
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One small action
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In the first 7 days
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That proves, “This works—and I can do this.”
That could look like:
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Two workouts instead of a full plan
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One sales script instead of a full funnel
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One post instead of a 30-day challenge
Momentum builds confidence. Confidence builds commitment.
Why Every Membership Needs a Clear Cadence
Familiar = safe.
If members don’t know:
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When content drops
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When calls happen
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What to expect each month
They disengage.
A strong membership has a simple, predictable monthly rhythm:
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Same structure
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Same timing
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Every single month
In Strategy Lab, for example:
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Deliverables drop on the 1st of the month
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Integration call happens on the first Monday
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Calls are short, focused, and actionable
No guessing. No chaos. No cognitive load.
When members can mentally say, “I know exactly how this works,” they’re far more likely to stay.
Accountability That Actually Works
Accountability doesn’t mean constant pressure.
It means lowering the barrier to action.
This can look like:
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Short sprints instead of 30-day challenges
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Weekend intensives
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5–7 day blitzes
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Rotating themes so not everyone has to do everything
Not every member will participate in every challenge—and that’s okay.
The goal is variety, relevance, and accessibility.
And yes—tease what’s coming next.
If someone is thinking about canceling and hears:
“Next month we’re doing X…”
You’ve just created a reason to stay.
Why Community Is the Real Retention Engine
People join for content.
They stay for community.
But here’s the mistake most people make:
They treat community like a broadcast channel.
Posting educational content nonstop is not community—it’s Instagram with comments.
Real community is built when:
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Members contribute
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Members help each other
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Members feel ownership
Crowdsourcing works incredibly well:
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Playlists
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Recipes
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Templates
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Wins
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Best practices
When members help create the resource, they feel invested in it.
Let Questions Breathe (This One’s Important)
This is something I learned years ago—and it works.
When someone asks a question:
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Don’t answer immediately
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Let it sit for a few hours
Why?
Because someone else will jump in.
Peer-to-peer coaching is powerful. It builds connection, confidence, and leadership within the group.
Eventually, you come in and:
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Validate what’s been said
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Add your expert lens
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Wrap the thread
But by waiting, you allow the community to become the community—not just a Q&A with you.
The Bottom Line on Membership Retention
Retention isn’t about:
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More content
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Faster replies
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Or constant creation
It’s about:
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Clear direction
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Simple structure
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Meaningful accountability
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And real connection between members
If people feel included, supported, and successful—even in small ways—they stay.
And that’s how memberships actually scale.