By Mordechai Schmutter

Once again, it’s time for our annual tax tips column, which I’ve been pushing off and pushing off, but now it’s almost April 15, and I have to write it.

I keep pushing it off, because doing taxes is incredibly boring. I guess it’s different if you actually have money, but filling in mostly zeroes is not that exciting.

Sure, accountants don’t find it boring. But that’s because they’re making money doing it. Getting money relieves some of the boredom of doing anything. Look at your job. And if you’re still in school, look at your teacher’s job. You’re both talking about the same subject, yet you’re bored and he is not. Why is that? Because he’s getting money for it. Sure, it’s very little, and he might not see it for six months, but it’s still money. Whereas you’re paying money to be there.

And so too our taxes. The accountant is making money, if you have any left when you’re done, but you’re not. You’re figuring out whether you have to pay the government even more money than you already did, or whether you paid them too much and have to get some back, and it takes several days to figure this out.

“Can’t we let this go? This was last year!”

So nobody really wants to think about doing their taxes before they actually do it, and thus, a lot of people come in unprepared.

So here are some things to make sure to have before sitting down to do your taxes. My advice is not to actually have all of these things, because there’s no more welcome relief than getting up in the middle to get things, and hoping your spouse finishes everything else while you’re gone. I come back eating something, and my wife’s like, “Where is that file you were supposed to get?” and I say, “Oh. That’s right.” And I leave again.

But obviously, if you’re doing this with a tax professional, and you have to go to his house or something, you should bring everything you need, because if you think he sighs a lot when you don’t know the answers, think about how much he’s going to sigh when he realizes you didn’t even bring the paper that has the answers on it. My advice is to load your entire filing cabinet into the back of your car, so you can keep going out to your car for things. This brings us to the first thing you need:

– An accountant. If you don’t know any accountants, then you’re probably not Jewish, and you can do your taxes on Pesach. The other option is to get

– Tax software, such as TurboTax.

Should you buy tax software, or hire a tax professional? I’ve looked into it, and I’ve found that most tax professionals suggest that you hire a tax professional. On the other hand, most tax professionals are also really busy this time of year, so this probably isn’t a good time to bother them.

Tax software also costs less money, but tax professionals might be able to save you more money in the long run, especially if they know you and have to see you in shul afterward. If TurboTax is so interested in saving you money, how come they make you buy a new copy every year? I understand that the tax laws change, but shouldn’t they put something in the program that allows you to just install updates? The answer is that the people who would develop such a thing are the same people who make even more money off the fact that you have to buy a new one every year.

– Tax information. I keep receiving important tax information in the mail that I’m afraid to read. All I know is that it says, “Important tax information enclosed” on the outside of the envelope, so I know to give it straight to my wife. I’m afraid to look. It’s either going to say that I made too little money, or that I owe too much in taxes.

– Tax forms. This is complicated because they all have numbers on top, and many of them have the same number, such as 1099. By my count, there are at least 9 kinds of 1099. Isn’t that what the number system is for? How did they manage to get all the way up to 1099? How many trials and errors did they have to go through to settle on that one? And why are there any numbers? Why don’t they just call EVERYTHING a 1099?

The whole thing is complicated. There’s a W-2, and then there’s a W-4, which apparently isn’t just two W-2s, and then there are 9 kinds of 1099, and then there’s a 1040, which I think is what cops say before they sign off on their walkie talkies, to let the operator know that they were paying attention.

Also, some of the forms are called “forms,” but some are called “certificates,” and some are called “schedules,” such as the 1040 Schedule D, which sounds like something you’d use to check when the bus is coming on holiday weekends. I don’t understand how these are “schedules.” I thought schedules were about the future. Why do they use distracting terms that also mean other things? Why can’t they just give it another number?

– Proof of income. You need proof. You can’t just say, “I made money; here’s some of it.” The government’s going to be like, “Whoa, whoa, wait a minute. Are you SURE you made this money? Because otherwise we don’t want it. If this is the same money you made last year . . .”

But for the most part, you need a W-2, which your employer will send you on his own, without you even bugging him. That will come on time. The W-2 tells you how much money you’ve gotten from your employer last year, in case you’ve forgotten. This is where everyone tries to mess over everyone else. The employer can just as well NOT fill out a W-2, but then he’d get taxed on that money. A W-2 is his way of saying, “I don’t have it; he has it.” This is how they throw you under the bus.

If you’re self-employed, you will also get a 1099-Misc.

“But if I’m self-employed, who’s sending me this 1099-Misc?”

I don’t know. It’s Misc. It’s one of the mysteries of the universe. But you’ll get them. No one wants to pretend they still have money that they already gave you. In my case, I get 1099s from places such as Hamodia that, over the course of the year, sent me some money even though I don’t actually work there. Out of the goodness of their hearts, I guess.

– Proof of expenses, and I don’t just mean mailing them your kids. “Look, he has braces. You think he was born with those?” I think you have to send your dentist a 1099.

You should also bring your receipts. Everyone always says to keep your receipts, but they never say which receipts to keep, and every single thing you ever buy comes with a receipt. I keep my receipt in one of the shopping bags, and then I reuse that bag as a garbage bag, and the receipt gets thrown out. Receipts are also hard to keep, because they’re on crinkly loud pieces of paper that are about two inches wide and a half a mile long. I don’t have any folders shaped like that. The best you can do is crumple it up and put it in a big box of crumpled receipts that you will never ever go through in a million years. So no one really reports all their expenses.

– Social security numbers, such as yours, your spouse’s, and your children’s. If you’re like me, you’ll remember about half of your spouse’s social, and none of your children’s, because when you have children, you start repurposing the part of your brain that used to remember new things. But you probably have them written in Hebrew somewhere, in case someone breaks into your house and decides to steal a single piece of paper. Like most socials that are stolen are on little pieces of paper during robberies.

You should also bring your

– Spouse, because you can’t do your taxes without your spouse present. If you don’t have one, get one. It’s convenient, and there are plenty of things you can do as a couple, such as file jointly, which is romantic.

– Last year’s tax return–so you can see what you said last time. You don’t want to keep giving different measurements for the size of your home office. Unless the amount of papers you have to keep is slowly taking over more and more of your house. v

Mordechai Schmutter is a weekly humor columnist for Hamodia and is the author of four books, published by Israel Book Shop. He also does freelance writing for hire. You can send any questions, comments, or ideas to

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