business taxes, General Information, RUNNING YOUR BUSINESS, Self Employed, TAX DEBT RELIEF, Tax Reduction, TAXES

Staying Out Of Trouble With “Gigs”

hustle led signage

In our Chicago South Loop Tax Preparation office, we often help people with tax bills through our tax debt help services. After seeing so many get into tax trouble with their side gigs, we decided to give some pointers on how to stay out of trouble for those with side gigs.

Let me give you a scenario: You’ve got a great job, and you’re moonlighting as a graphics designer on a freelancer website. All your clients are paying you through PayPal & CashApp, and honestly, you’re cleaning up. An easy extra couple thousand dollars each month. How do you report that income?

Legally, you’re bound to report ANY income you have, but these days, with so many folks doing their side gigs, are you actually reporting it? There’s actually even a darker side to this, though, and it’s nothing really new. Tipped employees – those like servers and bartenders who have for years existed on tips from their customers, have had this challenge for decades. Legally, they, too, are required to report all their income. Do they?
Schedule-button-nbor click here to call us 1-855-743-5765.

So what happens when you don’t report all of your income? You could get audited, if you earn over a certain amount the third party vendor can report your income to the IRs, but sometimes, the real place where not reporting your income can trip you up is… when you want FINANCE anything. In many cases, your ability to borrow money is based strongly not only on your repayment history, but also on your income. Guess where the bank or lender gets that information? Your tax returns, especially if you are a W2 employee.

Now, before you go and fall on your sword and claim every dime, understand there are a myriad of ways in which you can mitigate your tax bill even as you claim every dime you make. It could be by forming a S-corp, funding a retirement account, or shifting your income, starting a nonprofit, trust, or any one of a number of ways. As a result, though, especially if you create a so-called “pass-through” entity, you’ll have the ability to claim the income you’re legally responsible for AND make use of the deductions and protections afforded to these types of entities.


More importantly, it’s not expensive to set these up and the bookkeeping and tax preparation is very simple in such a small business. In the end, you’ll have the best of both worlds.

Although we’ve given you the basics, this is not an all-inclusive article. Should you have questions, or need business tax preparation, business entity creation, business insurance, or business compliance assistance please contact us online, or call our office at 855-743-5765. Make sure to join our newsletter for more tips on reducing taxes, and increasing your wealth.

Never miss another tip again! Join our newsletter, to receive tax reduction/wealth building tips delivered right to your inbox!

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s