You can spend weeks debating a pricing change…

Or months building the “perfect” onboarding flow.

Even better: You can spend years dreaming about a new product tier you never actually launch.

Meanwhile, the market moves. Member expectations evolve. And your competitors test, fail, learn, and ship again.

Most operators don’t just lose ground by failing. They lose ground by standing still.

I’ve seen more potential wasted by inaction than you’d believe. I’ve watched entire teams become forever stuck in endless analysis, vetting and debating while their competitors and peers continuing executing - not on perfect ideas, but ideas that are formed enough to try and then learn from.

I’m talking about failure.

It’s something that many operators will try to avoid at any cost: Analyzing, planning and believing that certainty is just one more meeting away.

But the reality is that there’s a fine line between playing it safe and being effective.

And with every incremental decision made in order to squeeze a bit more certainty out of your situation, you’re also giving something up.

Let’s dive in.

In membership, the biggest missed opportunities rarely come from bad experiments. They come from the experiments never run.

A few weeks ago I had an interesting conversation with a client at Memberful who told me that they felt like years of progress had been lost over an ongoing debate about pricing.

For months, their leadership team went back and forth. How much should they raise rates? Should they introduce new tiers? Should they test the new offer first?

Every scenario was analyzed, every “what if” discussed, and every meeting ended with another round of questions.

The result? Nothing changed.

Members stayed underpriced. Growth stalled. And worse, their momentum died.

And that’s just the cost of hesitation on the surface.

Going deeper, it’s not just the revenue left on the table. It’s the erosion of energy, confidence, and clarity. It’s the loss of momentum.

Things that often take an operator years to build, and even longer to rebuild.

Here’s the irony: Even if the client had tested the pricing and gotten it wrong, the loss would have been temporary. They could have course-corrected, gathered insights and tried again.

But by waiting? By avoiding risk? They lost something that can never be recovered - time.

This is the one that hurts - the loss of time.

Sure, revenue losses, higher churn rates and slowed acquisition sting, but the moment you realize that time is the currency you’re paying with, your perspective will change.

All operators have lives outside of membership. Families, friends, hobbies and things they do that aren’t directly related to their work in membership. However, these things often shape the true meaning behind that work and solidify their purpose.

Hesitation, inaction and endless analysis pulls an operator away from these things - because the cost of time is felt in every corner of an operator’s life.

So which sounds better:

Taking real action today on a promising idea that’s not fully complete?

Or continuing to analyze until it all feels comfortable while carrying the weight of wondering who’s in the background silently competing against you?

Both options will be felt in every corner of your life…

But only one of them will keep you up at night.

That client’s story is all too common. They didn’t just lose revenue by waiting on a pricing change - they lost the insights that only come from taking action.

If they had raised prices and it flopped, the lesson would have been immediate:

Even a “failure” would have given them a sharper map of their market. Instead, by avoiding the risk altogether, they learned nothing.

They traded one of the fastest paths to clarity for more meetings, more speculation, and more paralysis.

As an operator, you’re going to have to embrace failure on many levels. When I think back on the membership programs I’ve worked closest with, there are five high-value practices that are non-negotiable for leaders and operators aiming to maximize their effectiveness in membership.

Here they are:

1. Test faster than you plan.
Instead of overthinking a new benefit, ship it to a small group. Let members show you what’s valuable.

2. Redefine what failure means.
A failed experiment doesn’t mean you’re off course: It means you’re collecting data. Each failure narrows the gap between what you think will work and what actually does.

3. Use deadlines as discipline.
Unmade decisions pile up like dead weight. Force yourself to act within a timeframe. Even if you’re wrong, you’ll be wiser for the next iteration.

4. Watch for comfort creep.
When everything feels steady, it’s easy to think you’re safe. But comfort is often a sign you’ve stopped stretching. Ask: What risk am I avoiding right now?

5. Anchor in purpose, not perfection.
Failure without direction is reckless. But when your actions are guided by conviction, failure becomes refinement. Every miss sharpens your purpose and strengthens your resilience.

I’m encouraging you to shape and sharpen the above five points into a version that can be referenced by you and your team. However you collaborate, make it visible. Reinforce it. Hold yourself accountable to it.

Teams aligned on a shared vision around failure are teams that move without friction.

Failure rarely leaves an operator with regret. It leaves lessons.

Lessons you can carry forward. Lessons that sharpen your instincts. Lessons that make your next move bolder, smarter, and more effective.

The operators who build lasting memberships aren’t the ones who get everything right. They’re the ones who act, absorb learnings, and minimize regret by refusing to wait for perfect conditions.

Because the market will always change. The unknown will always be there.

And the only choice is whether you’ll be the one moving through it or the one watching from the sidelines.

So I’ll leave you with this question to consider until next week:

When you look back a year from now, will you remember what you learned by trying - or regret what you lost by waiting?

Think about it.