Good Work Requires Good Boundaries

File the Extension. Set the Boundary. Eat the Cookie.

Welcome to the first edition of “Taxing Thursday”. Given the time of year, I thought I’d keep it light but hopefully helpful.

“If you don’t prioritize your life, someone else will.”
— Greg McKeown, Essentialism

We’re in the final stretch of tax season—less than two weeks to go. You’re either getting it all done… or watching a slow-motion avalanche of client requests, missing documents, and “just one quick question” messages bury your mental state.

It’s around this time that everything feels urgent — but not everything should be.

If you’re still waiting on client documents, and they haven’t been delivered, then yes — you need to be putting them on extension. And that’s not a bad thing.

Filing an extension is not a bad thing.

Filing a rushed, inaccurate tax return? That’s a bad thing.

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“I Can’t Go on Extension!” (Spoiler: Yes, They Can.)

Every year, I get a few clients who say they absolutely cannot go on extension.

Of course, this conversation usually happens before they’ve sent me a single document.

Here are the two most common reasons I heard this year:

“If I file an extension, I’ll get audited.”

“If I file an extension, I’ll get kicked out of my IRS payment plan.”

Let’s clear that up:

• There is no evidence that filing an extension increases audit risk.

• However, filing an inaccurate return? Absolutely might.

Some clients say, “We can just fix it later!”
That sounds nice — but let me be clear: No.

I’m not filing a return that I know is incorrect. And here’s the kicker: The Internal Revenue Code does not explicitly provide for a taxpayer to file an amendment or for the IRS to accept the amendment. Rather, amended returns are “a creature of administrative origin and grace” (Badaracco, 464 U.S. 386 (1984)

Now, about payment plans (installment agreements):

As long as the return is filed by the extended deadline and you pay any balance due by the due date, the installment agreement will not be terminated.

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When Clients Cross the Line

These types of client demands — “No extension!” — are just one of many ways boundaries get tested this time of year. The pressure, the urgency, the assumptions that you are always on-call to clean up the chaos.

We have all had that client who thinks we live for only them. That we eat, sleep, and breathe their tax matters.

We joke about it, but the truth is: when we don’t have strong boundaries in place, we become complicit in the madness.

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The 100-Hour Week Lie

Another tax season classic: the social media flex of the 100-hour workweek.

“It’s tax season. I worked 100 hours this week. That’s just what we do!”

No. That’s what you chose to do.
Some of us are working 40–50 hours, going to the gym, eating dinner with our families, and yes — sleeping. (Some tax pros even go on vacation during tax season - it is entirely doable!)

Do I judge people who work 100 hours? No.
If you love it, go for it. But if you’re exhausted, complaining online, and dreading every day? That’s not a badge of honor — it’s a red flag.

And working yourself to the point of stress-induced health problems will only lead to one thing: you dying at your desk.

I have a great desk and chair.
I’d prefer not to die in them.

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Young Josh Had No Boundaries

Years ago, I started out in the IT world. I was the guy people called at all hours. I’d jump at every request — even for free. I’d stay up all night fixing computers. I didn’t charge enough. I didn’t say no. I wanted to help everyone.

I also burned out.

“When you don’t have boundaries, you don’t just give away your time — you give away your power.”
— Terri Cole, Boundary Boss

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Boundaries Aren’t Optional. They’re Survival.

Boundaries are not something you develop overnight. They take work. But they are life-changing.

Some people can read a book like Boundary Boss or Essentialism: The Disciplined Pursuit of Less and implement what they learn. Others need more help.

That help? It’s called therapy.

I know “therapy” still makes some people squirm, but let me say this clearly:

Therapy is not a weakness. It’s a needed luxury. Almost as good as a week at a Four Seasons but much more economical.

If you feel angry, overwhelmed, or constantly resentful of clients and your workload… that’s your body and brain telling you something. Listen to it.

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No. Is a Complete Sentence.

You do not need to over-explain.

You don’t have to apologize.

You are allowed to say:

• “No, I can’t do that today.”

• “No, that falls outside the scope of our engagement.”

• “No, I’m not working this weekend.”

• “No, we’ll need to file an extension.”

• “No, I can’t discount your price.” (You can do pro bono or “low bono” but only when you choose to!)

No is not rude. No is a boundary.
And boundaries are what allow us to stay in business — and stay sane.

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Final Thoughts

If you're in the thick of it right now — tired, frustrated, overwhelmed — I get it. You’re not lazy. You’re not broken. You’re a human being with limits. We all have limits. And on social media, it can look like everyone else has the perfect business and life. Remember — people mostly post the good. They rarely show the hard days. We all screw up from time to time. It’s called being human. If we were perfect, we’d be cats, dogs… or raccoons.

You’re allowed to rest.
You’re allowed to say no.
You’re allowed to file an extension.
You’re allowed to require respect.
You’re allowed to only work with clients that “spark joy”.

Remember: You are not responsible for other people’s feelings about your boundaries.

Now go have a chocolate chip cookie (or your indulgence of choice), tell a client no, and file that extension.

What do you struggle with when it comes to boundaries?