Joshua William

May 12, 2026

You're Probably Paying Taxes Wrong on Your Police Side Income

Police officers are in a weird financial position.

You might have your regular W-2 from the department, overtime, 1099 security work, a spouse's income, investments, a rental property, or even a side business.

Then April rolls around and somehow the entire tax strategy is:

“Let's see what TurboTax says.”

That's not tax planning.

That's finding out what happened after it's already too late to change most of it.

Your tax return isn't your tax strategy

There's a major difference between filing taxes and planning taxes.

Filing looks backward.

Planning looks forward.

If we're sitting down in the middle of the year, we can start asking better questions.

How much are you actually going to make this year?

How much has already been withheld?

How much 1099 income are you expecting?

What legitimate business expenses are you going to have?

Are you properly tracking them?

Are there retirement contributions worth considering?

Does your current business structure make sense?

Are you headed toward a big tax bill?

These are questions you want answered while there's still time to act.

Don't spend money just for a deduction

Cops love gear.

I know.

But spending $5,000 just because somebody told you it's a “write-off” can still mean you're $5,000 poorer.

A tax deduction isn't free money.

The better strategy is figuring out what expenses actually make sense for your business and then making sure you're taking advantage of deductions you're legitimately entitled to.

Sometimes the best tax move isn't buying anything.

It could be changing withholding, making an estimated payment, contributing to an appropriate retirement account, improving your bookkeeping, changing how your business operates, or simply planning the timing of something you're already going to do.

Know the number before April

You should have a reasonable idea of where you stand before tax season.

That's especially important when you're making significant 1099 income.

Nobody wants to work security all year, spend the money, and then get punched in the face with a tax bill.

We'd rather identify the problem while we still have options.

If you're making W-2 and 1099 income and have no idea what your tax situation looks like, contact JGuards Finance. We'll look at the bigger picture, identify potential planning opportunities, and help you build a plan before tax season arrives.

Contact JGuards Finance to schedule a consultation.