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HeyCreator · Aug 21, 2026

Your Reminder Email Is Not A Reminder

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HeyCreator by Matt Ragland · HeyCreator

I hosted office hours last week and nobody showed up.

Not one person. I had a few maybes on the list, my assistant sent reminders the day before like we always do, and I logged on early with coffee, ready to go.

Four minutes later it was just the two of us talking about a calendar conflict and her husband’s dinner plans. We wished each other well and logged off.

That kinda stung, honestly. My first instinct was to make it mean something enormous — nobody wants this, wrong offer, wrong day, wrong me.

Then I asked one boring question. When did the reminder go out?

Yesterday. Which felt fine at the time. It always does.

And there it was. A reminder that goes out 24 hours early isn’t a reminder. It’s content. It lands, it gets read, it gets a polite nod — and then an entire day of real life stacks on top of it. School pickup. A meeting that runs long. Forty newer emails.

By the time your event starts, your reminder is archaeology.

The fix wasn’t a better invite or a bigger list or a more compelling promise. It was a shorter gap between the email and the thing.

So that’s the rule around here now. If RSVPs are light, we send again a couple hours out. Not because people forgot you. Because Wednesday happened.

Proximity beats politeness. Send it while they can still act on it.

I don’t love learning things this way. But an empty room is data, not a verdict — and this one only cost me four minutes and a little pride 😅

Matt “two hours out” Ragland

P.S. If you already have a newsletter and an offer but you’re not making consistent revenue from them — that’s exactly who Inbox to Income is for. I personally edit your newsletters and your offers, not just give feedback. [Apply here]

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