There’s always a point where benefits alone stop being enough.

The newsletters, the analysis, the perks - they’re all important. But these things aren’t at the foundation of why people really care about what you do.

At the end of the day, your members are staying for something deeper.

And if you want long-term loyalty from them, you have to learn how to speak to the things they hold so close.

Let’s dive in.

Open your homepage and read your pitch.

Ask yourself: Does this explain what I offer or does it express why it matters?

Because here’s what we know: people rarely join because your membership has the most benefits or the most hours of content. They join because it makes them feel understood. They join because it feels like a step toward the person they want to become.

But this is where most operators get stuck. They list features like a menu, hoping something will eventually stick, and then burn themselves out on keeping a long list of benefits alive - even if those benefits aren’t what’s truly driving the results.

Spend any amount of time with the typical member and ask them what causes them to stick around and I guarantee you that you’ll find the following to be true:

Their answers and reasons aren’t transactional - at all.

That’s about as far from transactional as you can get.

And this is incredibly important - because as membership operators, we must think in transactional terms when running a subscription-based business. It’s simply what’s required.

However, being able to switch between strategic, transactional thinking for your business to need-based and emotional thinking for your members isn’t something that comes naturally - but it must be developed.

After years of living and breathing membership, I can assure you this will always be true:

Your members will never care how well you manage revenues and cash flows. They will never care about your margins or profitability. They only care about the emotional outcome that unfolds when using your product.

And emotional outcomes are what drive real retention.

When a membership aligns with who someone wants to be, it becomes more than just useful - it becomes personal.

And when it’s personal, people don’t just use it, they return to it.

They advocate for it. They see it as part of their story.

So how do you build that kind of connection?

Start by designing for identity, not just utility. Your product should help answer a deeper question for your member:

“Is this for someone like me and can it help me become who I want to be?”

Here are a few of the most practical ways to translate that into real-world action:

1. Frame your offer around a transformation, not a task.
Don’t just say “new workouts every week.” Say “feel stronger, more capable, and more in control - every week.”
→ Speak to the emotional benefit your members crave.

2. Reinforce who they’re becoming, not just what they’re doing.
Give members moments that say: you’re making progress, you’re showing up, you’re one of us.
→ These aren’t “nice-to-haves”, they’re proof that the identity they want is within reach.

3. Build trust loops that strengthen the relationship.
Trust isn’t built in a launch. It’s built in the quiet moments, through small signals of reliability, tone, and intent.
→ Every interaction (even automated ones) is a chance to earn or lose that trust.

These loops might look like:

When trust loops are strong, your membership feels like a partner to the member: a partner that’s fully invested in the emotional outcome they desire.

You don’t need more features. You need more honesty, resonance and authenticity.

The membership market is beyond saturated, and one of the few ways left to cut through it all is to be honest, authentic and real about how your product is going to make someone’s life better.

So I’m challenging you to this:

Don’t ask “What do I offer?”

Ask: “What belief does my membership reinforce in someone’s life and how does it help them step toward it?”

And once you find that answer, double down on it. Design around it. Message to it. Let it shape every interaction and every snippet of copy you write.

And lastly, I’ll leave you with this:

Give someone a reason to see themselves in what you’ve built, and they’ll stop looking for something better.

That’s what drives real retention.

Think about it.

Tell me: How can I help you with your membership? Respond to this email and let me know (I always read every reply).

Share: I want Operator to be the most valuable thing that comes across your inbox each Tuesday. If I’m hitting that mark, share this newsletter with your staff, a team member or friend (just copy and share this URL).

See you next Tuesday.

-Michael