The Flop Hat: The Week I Forgot to Pay Us All

TL;DR: I missed payroll. People panicked. Paper checks were printed like it was 1997. And somehow, we all survived.

It Was a Thursday When I Realized

You know that quiet voice in the back of your mind that sometimes whispers things like “did you leave the oven on?” or “you never replied to that email from three days ago”?

Well, mine said:
“Is it payday?”

And that’s when I knew.
It was payday.
It was definitely payday.
And I had absolutely, 100% forgotten to run payroll.

Let’s Back Up

For context: we use ACH transfers.
Payroll is usually automated.
And I’m the one who’s supposed to press the metaphorical big green button.

We’re not talking about some 100-person operation.
This is a small business. But everyone still expects, you know, to get paid.

Normally, I run payroll by Tuesday at noon. That gives it enough time to clear by Friday.
Except this week?
Tuesday came.
Tuesday went.
And I... was deep in a spreadsheet about sales tax imports and tariff tables.

The Spiral Begins

At first, I was calm.
“Well, maybe the bank will process it fast this time.”
It won’t. I know it won’t. But denial is comforting.

Then came panic:

• “Can I backdate an ACH?” No.
• “Can I run a same-day batch?” Not with my current plan.
• “Can I ask everyone to wait till Monday?” Hilarious.

That’s when I realized:
I’d have to print paper checks.

Printing Paper Checks: A Medieval Experience

First off, I had to find the checks. The actual, physical checks.
I’m pretty sure I last touched them during the first wave of COVID, right before I also tried baking sourdough.

They were in a dusty box in the closet labeled “Emergency Use Only,” which now felt painfully prophetic.

Then came the printer drama:

• Ink low.
• Alignment off.
• Test print revealed my business logo from 2018. Complete with Comic Sans.

I burned through five sheets before getting one that didn’t look like a ransom note.

Breaking the News

I gathered the team in our Slack channel and typed:

“Hey team! Quick heads up — payroll will be a little different this week. You’ll be getting paper checks. From me. Personally.”

Cue reactions:

• 😬
• “Wait, what?”
• “Do you need help?”
• “Should I be worried?”
• “Are we still... getting paid?”

That last one hurt.
Yes, of course you’re still getting paid.
But the vibe had shifted from “professional small business” to “garage startup with a paper route.”

Hand Delivery: The Walk of Shame

I hand-delivered the checks.

It felt like Halloween, except instead of candy, I was handing out my embarrassment in the form of 20 lb. laser-printed rectangles.

One person literally asked, “Do I have to go to the bank for this?”

Yes. Yes you do.
Because I forgot to press one button on Tuesday.

Why This Flop Hurt

This wasn’t just a technical mistake. It was:

• A credibility hit. You never want your team questioning the reliability of payday.
• A systems flaw. If one person missing one task derails the whole thing, the system’s broken.
• A wake-up call. I needed backup plans. Reminders. Safety nets. Something.

Let’s be honest — we all wear too many hats. That’s the point of this blog.
But forgetting payroll?
That’s like a pilot forgetting to lower the landing gear.

What I Did Next (After I Stopped Cringing)

1. Built Payroll Into My Calendar — With Fire Alarms

I now have:

• A Google Calendar recurring reminder.
• A Slackbot that pings me.
• A physical sticky note on my monitor that just says “PAYROLL???”

Overkill? Maybe.
Necessary? 100%.

2. Set Up a Secondary Admin (Just In Case)

No one should be the only person who can run payroll.
If I get hit by a golf cart tomorrow, someone else should be able to make sure people eat.

3. Upgraded My Payroll Plan

We now have same-day ACH capability as a backup.
It costs a bit more, but it’s cheaper than losing trust.

4. Told the Team the Full Story

I could’ve brushed it off. I didn’t.

Instead, I owned it:

• Told them exactly what happened
• Explained what I was putting in place to fix it
• Made a joke or two at my own expense

And surprisingly, people appreciated it.

Accountability beats silence every time.

What I Wish I’d Done Sooner

• Set up payroll automation triggers
• Kept an emergency fund for same-day backup
• Scheduled a weekly “Oh Crap” checklist
• Documented a backup payroll process (written, not in my head)

If you’re running a small team — whether it’s two people or twenty — do this before you have your own Paper Check Week.

Lessons for You (So You Don’t Repeat This)

1. Never Assume Automation = Done

Just because something can be automated doesn’t mean it is.
You still need to check that the system ran, the settings are current, and your input wasn’t you forgetting entirely.

2. Build in Redundancy

If you’re the only one who knows how to do a thing, you’re the bottleneck. That includes payroll.

Train someone else. Write it down. Have a backup.

3. Your Team Doesn’t Want Perfection — Just Communication

They didn’t need me to be flawless.
They needed to know:

• It wasn’t permanent
• It wasn’t financial trouble
• It wasn’t going to be normal

Be real with people. That’s how you keep trust, even when you mess up.

The Silver Lining

People still cashed their checks.
No one quit.
In fact, we turned it into a bit of a joke.

Now, every Friday, someone says,

“Checks coming by carrier pigeon today or what?”

And honestly? I deserve that.

But we’re better for it.
Because now we’ve got systems.
We’ve got backups.
And I’ve got a blog post to remind me what happens when I forget Tuesday.

Your Turn

If you’ve ever:

• Missed payroll
• Overpaid someone
• Sent a W-2 to the wrong address
• Forgotten to even hire someone after saying you would...

Congratulations, you’re a small business owner.

Tell your flop. Laugh at it. Learn from it.

Or at the very least — set a payroll reminder before next Tuesday.