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

06/18/2026

🧾 Tax Season Survival Guide

Want to navigate tax season like a pro? Here's your battle plan:

â—Ź Know your numbers
â—Ź Track EVERY transaction
â—Ź Keep EVERY receipt

Your documentation is your ultimate defense.

Share this with someone who needs a tax strategy reset.

06/16/2026

đź’Ż The tax philosophy that has saved my clients thousands

There's a world of difference between "tax avoidance" (legal) and "tax evasion" (illegal).

Smart taxpayers don't ask, "How can I avoid taxes altogether?" They ask, "How can I LEGALLY minimize what I owe within the system?"

This shift in mindset—from fighting the system to understanding it—is what separates those who constantly battle the IRS from those who strategically reduce their liability.

The tax code is complex by design, with legitimate deductions and credits built in for those who know where to look.

What's your approach to taxes? Avoidance or strategic planning? Comment below!

06/15/2026

By the time a notice arrives, you're already in a reactive position.

Explaining. Defending. Trying to fix something that could have been prevented.

The people who stay calm during tax season aren't lucky, they stayed ready. They classified correctly, collected the right forms, and documented consistently.

Reactive is expensive. Proactive is peace of mind.

💬 Are you currently proactive or reactive with your taxes? Be honest 👇

06/15/2026

An audit-resistant system isn't complicated, but it is structured.

You collect and verify W-9 information.

Never let anyone do work you're going to pay for without getting a 1099, and do your best to verify it, because if it's wrong, it's on you.

You understand how payments are processed.

You avoid duplicate reporting.

You align your operations with your classifications.

And you document everything, not just for the IRS, but for yourself.

Because if a question comes up later and you already have the answer, that's what preparation looks like.

Structure your process before the IRS structures it for you.

06/12/2026

One of the biggest sources of confusion right now is the difference between a 1099-NEC and a 1099-K, and it's driving a surge in IRS notices.

The 1099-NEC is for direct payments to contractors.

Non-employee compensation. They changed the rule, it used to be the 1099 miscellaneous.

The 1099-K is for payments processed through a third-party platform, like credit cards or Venmo.

Sometimes both forms get issued for the same income. That's the problem.

You need to understand how your payments are being processed, because the form matters.

#1099

06/12/2026

Before anyone does a single hour of work for you, get the W9 first.

It doesn't matter how great the work was. It doesn't matter that you paid fairly. If the paperwork is wrong when tax season comes, the liability lands on you.
Not them. You.

The fix is simple and it costs nothing but a few minutes upfront.

Never let anyone do work for you that you're going to pay without getting that form first.

đź’ľ Save this so you never forget it.

06/11/2026

✨ The moment a client realized their IRS debt wouldn’t last forever.

A client recently called, convinced they’d be stuck paying the IRS for life. But here’s what most people don’t know—the IRS has a Collection Statute Expiration Date.

Once the 10-year collection window closes, certain tax debts legally expire. No loopholes, no tricks—just part of the tax code.

This isn’t about avoiding responsibility—it’s about understanding your options. If you're overwhelmed by tax debt, there may be a way forward.

Comment "RELIEF" if you want more insights on tax debt solutions!

06/10/2026

You don't have a tax problem. You have a preparation problem. đź“•

Most people lose to the IRS because they didn't understand their options before it was too late.

This book changes that.

Inside Fight Back Now, you'll learn IRS installment agreement options, offer and compromise strategies, collection due process appeals, IRS transcript analysis, and the five-step framework to move from chaos to control.

Because before you can solve a tax problem, you need to understand where you are.

Read it. Study it. Use it.

Go to FightBackNow.com and become a Freedom Fighter today.

06/10/2026

Classification isn't about what title you give someone. It's an operational decision.

Do you control their schedule? Their tools? How the work gets done?

If yes, that's an employee. The form you file doesn't protect you. Your operations do.

If the two don't match, you're exposed.

Get your classification right before someone else questions it.

đź’¬ Drop a question below if you're unsure how to classify someone on your team.

06/09/2026

⏰ The extension clock is ticking in ways you don't realize.

Yes, you can extend your filing deadline. But what they don't tell you clearly enough:

Your MONEY is still due on Tax Day. Period.

Every day after the original deadline, interest compounds on your unpaid balance. It's like taking out a loan from the IRS—at their interest rates, not yours.

The most expensive words in tax planning? "I'll worry about it later."

Set a reminder right now to estimate what you'll owe BEFORE the deadline.

Save this post if you've been relying on extensions without understanding the true cost!

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Chicago, IL

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Thursday 9am - 5pm

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