That Payroll Guy

Cringe Week 2026 is almost over 😮‍💨

Why is this week Cringe Week? Well, let me explain…

Working for a service bureau, we have a responsibility to keep our clients informed of regulatory and processing updates…to include national holidays. No matter how much we communicate in advance, clients are surprised when items arise…

“Why is my check date Thursday?”
“Why am I being asked to process my payroll by Thursday for my Tuesday check date?”
“Wait….why are you all closed Friday?”

This year marks Year Six of Juneteenth being a national holiday. And yet…here we are with not only surprised clients, but then we encounter those who don’t mind speaking their prejudiced opinion regarding the holiday. There were so many “amazing” contributions that came across my desk as far as frustrations, but this year’s top comment was a client who expressed her disappointment regarding “the bogus holiday”.

Imagine reading these comments from payroll professionals, HR managers, and, yes, even owners of companies. Also, put yourself in my position reading this as a *looks at back of hands and arms* Black male.

The irony is that every year we spend more time debating the holiday than understanding it.

Juneteenth isn’t about taking a day off. It isn’t about politics. It isn’t about inconveniencing payroll schedules.

It’s about the day freedom finally reached people who had been legally freed for more than two years but had never been told.

Think about that for a second.

As payroll professionals, we’re in the business of communication, compliance, and making sure people receive what they’re entitled to. Juneteenth is literally a reminder of what happens when information doesn’t reach the people who need it.

So yes, your payroll may need to be processed a day early. Yes, your check date may shift. And yes, our offices may be closed.

We’ll survive. 😏

What we shouldn’t do is lose sight of why the holiday exists in the first place.

Happy Juneteenth. ❤️🖤💚

I’ve sat through HUNDREDS of presentations on generations in the workplace over the years. Some good. Some forgettable. Some that made me question my life choices before the caffeine kicked in. 😂

But this one? Different. Very different.

By far the BEST presentation on generations in the workplace I’ve ever heard. Period.

absolutely crushed this session. The perfect mix of research, humor, storytelling, and those “well damn…he’s right” moments that had the entire room locked in.

One of the biggest takeaways for me:
“Technology is only new if you remember the way it was before.”

Simple statement. Massive perspective shift.

This wasn’t one of those sessions where you walk out with a couple buzzwords and a slide deck you’ll never open again. This was the kind of presentation that actually changes how you think about leadership, communication, hiring, training, and workplace expectations across generations.

Payroll Congress…THIS is how you do a keynote. 👏🔥

FutureOfWork Generations WorkplaceCulture ThatPayrollGuy HR HumanResources PayrollLife

Here I come!! ✈️

Alright TPG family, I’m stepping out of payroll for a second but not out of purpose 👀

Y’all know me as That Payroll Guy. I show up, solve problems, answer questions, and pour into this community every single day.

Today I’m showing up as Dad.

My daughter Gia just made the William Byrd Middle School Cheer Team for the 2026–2027 season 📣🐾
And yeah… I’m proud proud.

Now here’s where the worlds connect.

Just like in payroll, it takes a village to make things run right. These girls are raising funds for uniforms, competitions, camps, and all the behind-the-scenes work that makes it happen. Sound familiar? 😏

So I’m reaching out to my network. The same network I show up for every day.

👉 Sponsorship is $250
👉 Your business gets featured on their banner all season
👉 You’re investing in the next generation

If I’ve ever helped you with payroll, content, guidance, or even just gave you something that made your day easier…

I’m asking you to show up for Gia.

Drop a comment, send me a message, or tag a business owner who might want to support.

Let’s show her what this community is really about 💪🏽

And if nothing else, flood the comments with some love so she knows she’s got a whole payroll army behind her ❤️

SupportTheNextGen GoTerriers

First in-person conference of the year… and we’re kicking it off RIGHT 👀

I’ll be speaking this Thursday at the Maryland Statewide Conference, and I’m not gonna lie…I’ve been ready for this one.

There’s just something different about being in the room. The conversations. The energy. The “wait…you’re THAT payroll guy?!” moments 😂

We’ve been doing a lot virtually, but nothing replaces real connection—and I’m looking forward to pouring into this community, sharing a few gems, and probably learning a thing or two myself. Also, I’m in dire need of a solid restaurant for seafood…so send me your options! 🦀

If you’re gonna be there, make sure you come find me. Let’s talk payroll, life, and everything in between.

Let’s get it.

“Become an entrepreneur or com* su #^{de!!!!”

Read that again.

Because that’s essentially where this conversation went under a post about 30,000 people losing their jobs.

For those who follow me on LinkedIn, you saw my take on the Oracle layoffs.

What you didn’t see coming…was someone turning that moment into a full-blown “just start a business” sales pitch then doubling down with one of the most reckless comments I’ve seen in a long time.

And this is the part that gets me…

We’ve gotten so comfortable packaging struggle into content, that we forget there are real people behind it.

People with mortgages.
Kids.
Medical bills.
Real pressure.

And somehow…we’ve convinced ourselves that the right response is:
“Have you tried entrepreneurship?”

No plan.
No context.
No empathy.
Just vibes and a funnel.

Let me be clear…

Entrepreneurship is a path.
Not a parachute.

And it damn sure isn’t something you throw at someone who just lost their livelihood like it’s a motivational quote off a coffee mug.

But turning layoffs into a lead magnet?

That’s nasty work.

We can disagree all day.
We can challenge ideas.

But if your first instinct in someone else’s storm is to sell…

You’re not helping.

You’re hunting.

Do better.

It’s my birthday today.

Which means two things.
1. I’m officially older
2. Payroll is still due on Friday

Another year older, another year wiser, and another year of doing what I love. Helping people understand the wild world of payroll while building something bigger than I ever imagined when I started this journey.

I’m grateful for every opportunity, every client, every conference, every conversation, and every person who supports the work I do.

And yes… I’ll still answer payroll questions today.

But only after cake.

DON’T LET ANYONE RUIN YOUR FRIDAY ‼️

At some point today…
someone will say

“This will only take a minute.”

It will not.