Law Office of Steven A. Leahy, PC

Law Office of Steven A. Leahy, PC Attorney Steven A. Leahy has served the Chicago area and beyond over the past two decades. He works

You can call them a "contractor" all you want.The IRS doesn't care what's on the paperwork, they care how the relationsh...
06/05/2026

You can call them a "contractor" all you want.

The IRS doesn't care what's on the paperwork, they care how the relationship actually works.

Do you control their schedule? Provide their tools? Require them to work only for you?

That's an employee. And the back taxes and penalties that come with misclassification don't care about labels.

The biggest tax mistakes aren't made on purpose, they're made out of convenience and a title that seemed harmless.

Don't let a label cost you thousands.

Drop your questions about worker classification below. 👇

06/04/2026

❌ The #1 tax extension myth that costs Americans millions every year

"I filed an extension, so I have until October to pay my taxes."
WRONG. Dead wrong.

An extension gives you more time to PAPERWORK, not more time to PAY.

Your payment is still due on Tax Day, extension or not. Every day after that, interest compounds on what you owe.

This misunderstanding is so common that I see clients shocked when they realize they've been accruing penalties for months.

Double tap if this is news to you! You're definitely not alone.

The IRS doesn't need an agent to catch you.Most tax returns are filed electronically, which means a computer already has...
06/03/2026

The IRS doesn't need an agent to catch you.

Most tax returns are filed electronically, which means a computer already has your numbers.

When they don't match what your employer or bank reported, the system flags it automatically.

No human judgment required.

People assume tax mistakes slip through the cracks.

But there are no cracks anymore.

It's not enforcement, it's just automation.

Save this as a reminder that the system doesn't need to be watching you to catch you. 📕

06/02/2026

⏱️ What took tax investigators years now happens in an afternoon.

The computational power behind modern tax enforcement is staggering. Financial secrets that remained successfully hidden for HALF A CENTURY are being uncovered with ease.

This isn't about working harder - it's about the exponential capabilities of algorithmic detection that no human team could match.

Have you updated your financial practices for this new reality? Drop a 💻 if you're prepared.

The IRS doesn't need to investigate you. 📋Your paperwork will do it for them.Most people think tax trouble comes from be...
06/01/2026

The IRS doesn't need to investigate you. 📋

Your paperwork will do it for them.

Most people think tax trouble comes from being targeted. It doesn't.

It comes from documents that tell the wrong story on their own.
A missing record. An inconsistency. A form that doesn't match.

That's enough.

You don't need bad intent to have a bad outcome. You just need messy paperwork at the wrong time.

Get organized. Know what you're submitting.

Save this before tax season sneaks up on you. 💾

Has your paperwork ever caused you an unexpected headache? Comment below 👇

05/29/2026

Worker Misclassification

The IRS doesn't care what you call someone. They care how the relationship actually works.

They look at three things, behavioral control, financial control, and the relationship itself.

Who controls the work? Who provides the tools? Is the person economically independent? Do they have other clients? Is there a contract?

You can have a perfectly drafted independent contractor agreement and still lose, because the facts don't match the document.

Classification is not a form decision. It's an operational decision. And if your operations don't support your classification, you're exposed.

Save this if you have contractors working for you.

#1099

Most IRS problems don't start with fraud. 📋They start with paperwork.Not schemes. Not bad intent. Just a missing form, a...
05/29/2026

Most IRS problems don't start with fraud. 📋

They start with paperwork.

Not schemes. Not bad intent. Just a missing form, a late filing, a box left unchecked.

That means most IRS problems are completely preventable.

You don't have to be doing anything wrong to end up with a serious tax issue.

You just have to be disorganized at the wrong time.

The good news? Paperwork is fixable.

But only if you catch it before the IRS does.

Save this as your reminder to get your documents in order. 💾

What's one tax document you always struggle to find? Drop it below 👇

05/28/2026

🎯 Random tax audits are officially a thing of the past.

With 95% of returns filed electronically, the IRS can now automatically review EVERY submission. Their algorithms have evolved from randomly selecting returns to precision targeting specific patterns.

The days of "getting lucky" and avoiding detection are over - now it's all about algorithmic precision.

Save this post if you want to stay informed on modern tax enforcement methods.

05/27/2026

Backup Withholding

Something most people completely overlook, backup withholding.

If you pay a contractor and they fail to provide a valid taxpayer ID, like a Social Security number, you are required to withhold taxes. It's not optional. It's required.

Never let a contractor start work unless you get the W-9 from them. Have them sign it and verify the number.

Because if you don't, the burden falls on you. The IRS doesn't go after the contractor, they go after the employer.

Documentation matters. Process matters. The goal should always be to reduce risk.

Save this, every payment without proper documentation is a risk.

05/26/2026

🚨 Haven't filed taxes in years? You're getting human attention.

Here's the reality of modern tax enforcement: most returns only face algorithmic review, but clear compliance gaps trigger manual examination.

The computers flag the anomaly, but actual people investigate your story. This is one area where the human element remains critical.

Tag someone who needs to get their tax situation straight before they end up with unwanted attention.

Address

2525 Waukegan Road Suite 210
Chicago, IL

Opening Hours

Monday 9am - 5pm
Tuesday 9am - 5pm
Wednesday 9am - 5pm
Thursday 9am - 5pm

Telephone

+13126646649

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