How to Decide Whether to Hire an Accountant This Tax Season

Your New Year’s hangover has barely subsided, and TurboTax and H&R Block are all up in your grill with various offers. Let it be known that 2016 has already been ruined because, we, the citizens of these United States, have to start worrying about filing our taxes. So, what’s the move? Do you take the freebie TurboTax route or do you pay your grandparents’ friend’s daughter, Susan — who is a CPA, has a two-car garage, and a dog named Ringo — to do them? I caught up with Loyola University Chicago law professor Samuel Brunson for his take.

Professor Brunson is on the faculty at Loyola’s law school and specializes on how federal income tax affects taxpayers, making him a go-to guy on the subject. He also does not have a dog named Ringo, as far as I know. We didn’t talk about that. Here’s what he tells me:

Tax preparation software is good enough for pretty much any Average Joe — or, at least, an Average Joe who is an employee, receives a W-2, and doesn’t have much financial complication beyond maybe owning a house and making charitable contributions — but any given individual will need to figure out how comfortable he or she is with computers and with money. For a person who is less comfortable with computers or money, or who is going to spend the next three years worried that she did something wrong, it may make sense to engage a professional, if only for the peace of mind.

There you have it, folks. Most of you are in the clear. File for free. Science can even help put you in the mood to knock it out. But what about the rest of us? Let’s segment out Brunson’s caveats. Here’s why you might want to hire an accountant:

Your return = the Rosetta Stone

I’m a freelance writer. My tax return is messier than the wall after a drug deal has gone wrong in Scarface. I pay my mother’s accountants to parse through my various W-2s, 1040s, 1099s, and I dunno-whats. I don’t even know if all of those numbers are right: That’s why I hire an accountant. Also, if you’re not poor like me, you probably require an accountant to sift through your donations, various properties, holdings, and Dom Pérignon bottle-related yacht damages. Although, if you’re loaded, you already knew that.

You aren’t auditioning anytime soon for Mr. Robot

If you aren’t the greatest with computers, it’s cool: It has a retro charm that will probably become “lit” right around the same time hipsters are done with vinyl. (But, ya know, maybe your kids should’ve taught you what’s up by now.) Visiting a CPA who looks miserable as he sits in a windowless office waiting for his next cigarette break? That’s old-school, baby!

The government strikes fear into your heart

Did you buy a bunch of guns when Obama mentioned that a school full of murdered children wasn’t a good thing? Are you pretty certain Joe Biden is watching you via your Dell webcam as you read this? Are you seriously considering voting for Ted Cruz? If your answer to any of these questions is “yes,” you might suffer from IGF: Irrational Government Fear. The IRS audits about one percent of filers, so you’re probably fine using online software. Unless this column is a conspiracy, itself, written by a pawn of the New World Order. How can you know? Better call Susan, the accountant.

You would rather do just about anything else than work on your taxes

Part of what an accountant does for you is … they do your taxes. They help handle the paperwork, inoculate you against audits, find deductions you weren’t expecting, and generally relieve you of a hassle Ben Franklin equated nearly with death itself. You made enough money this year to afford it, champ. And that’s why you have to pay up.