How to know if you have this problem

If you want to know whether you have a retention problem, don't look at your email metrics.

Look at your support tickets.

Specifically, look for these three questions …

If you're getting these questions a lot, you don't have a communication problem.

You have a visibility problem.

Your customers are confused. They don't know what progress looks like. They don't know if they're on track or off track.

And confusion is what churn looks like before it becomes churn.

Here are some other symptoms I see all the time …

Symptom 1: Churn spikes after the second or third purchase

This means customers are evaluating before the product has a real chance to work. They're not seeing progress fast enough, so they bail.

Symptom 2: Strong reviews, weak repeat purchase rate

This means customers like the product, but they don't have a clear path to success. They're not sure how to use it consistently or what "winning" actually looks like.

Symptom 3: Subscriptions don't stick

Customers subscribe (often for the discount), then cancel after the first or second cycle. Why? Because they're not confident it's working yet, and subscription feels like a commitment they're not ready to make.

Symptom 4: Customers buy the smallest option and disappear

This is under-commitment. They're playing it safe because they're uncertain. And when you play it safe, you often don't use enough product for it to actually work … which becomes a self-fulfilling prophecy.

Symptom 5: Retention requires constant promotions

If you need discounts to get people to reorder, they're not staying because of results. They're staying because of price. And that's fragile.

Here's the pattern …

When customers can't tell if it's working, they hesitate. They wait. They "see how it goes."

And hesitation kills retention.

The fix isn't more emails. It's not a better loyalty program. It's not a bigger discount.

The fix is making progress visible.

You need to help customers recognize that it's working before the final result shows up.

Because if they can't see progress, they'll assume there isn't any.

Tomorrow I'm going to give you the simple system to fix this … what I call the "first win" framework.

It's not complicated. It doesn't require a massive overhaul. But it changes everything.

For now, just do this …

Go look at your support tickets from the last 30 days.

Count how many times customers are asking some version of "Is this working?"

If it's more than a handful, you've got a visibility problem.

And that's actually good news … because visibility problems are fixable.

See you tomorrow,

Jeremiah

P.S. One more symptom to watch for: if your retention varies wildly depending on where customers came from (Facebook vs Google, influencer vs cold traffic), that's a sign you're pulling in people with mismatched expectations. They're evaluating your product through the wrong lens. I'll talk more about that in a future email.

100% Typo Guarantee … This message was hand-crafted by a human being … me. While I use AI heavily for my research and the work I do, I respect you too much to automate my email content creation.

There was no review queue, no editorial process, no post-facto revisions. I just wrote it and sent it … therefore, I can pretty much guarantee some sort of typo or grammatical error that would make all my past english teachers cringe.

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