May 21, 2024
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Linking Northern and Central NJ, Bronx, Manhattan, Westchester and CT

We all know the saying, “There’s no such thing as a dumb question,” although yeridas hadoros since the saying was formulated has made us question whether it is in fact true. But there is definitely a dumb time to ask certain questions.

Accounting questions, for example. I don’t know what you do for a living, but imagine all of the projects that you work on over the entire year were all due on the same day. And imagine there was only a three-and-a-half-month window in which to make any real headway on any of them, and that all of your clients were aware of when that one day was, and they each decided, on their own, that they don’t have to even think about sending you what you need in order to do this job for them until the week of the deadline. And most clients, on their best day, will only send you about half of what you need.

“It’s okay; if there’s anything else he needs, he’ll play phone tag with me.”

And now imagine that that one week was also Pesach.

In this situation, the saying changes to, “Every question is a dumb question.” But that doesn’t mean that people stop asking questions because, I mean, it is Pesach.

And accountants have been dealing with tax questions ever since we first became a nation, and they had to answer questions like, “I just got paid for 210 years of slavery all at once, but I’m moving to the desert. Where do I file?”

Also, some questions are dumb to certain people but not to others. For example, frequent readers of my occasional tax column will realize that, to me, every tax question is an excellent question because I don’t know anything about taxes. But for example, my wife has taken a second (third?) job at an accounting office, and once in a while when I walk into the office, her boss will tell me about some of the ridiculous questions that people have asked him, and I smile and nod along, but to be honest I don’t get it. He’ll be like, “Can you believe someone asked me that question?” and I’ll nod, but I’ll be thinking, “So… what’s the answer?”

Like the accountant will say, “So this woman asked me if she could take off her sheitel as a deduction.”

And that’s it. That’s his whole story.

And I’m like, “So… so could she?”

And he laughs.

“Seriously. Could she?”

So in this article, I’m going to go through some great questions to ask your accountant, just not now. I’ll also try to provide some quick answers if I know them, based on either my limited knowledge of how things work or on the few words I was able to get out of my wife’s boss before he threw me out of his office. But I mean I have deadlines too.

Can I take off my toupee? {Please don’t.}

What if I’m a judge?

Do I need to send in my WD-40?

Do I have to pay taxes on salt?

Can I pay you under the table?

Wait, why do you want my social?

If I talk business in shul, can I take my membership off as a tax deduction? What percentage of davening do I have to talk business?

Wait, I can’t? Then why do people do it?

Do I have to send in my K-9?

My boss sent me a w-2, but I still haven’t gotten my w-1. Should I let him know?

If I keep my receipts in a shoebox, can I deduct the cost of the shoes?

If I pace around while I’m on business calls, what percentage of my property can I deduct as a home office? I have literally been everywhere.

I just got into a car accident while talking to you on the phone about my taxes. Can I deduct it? (NOTE: My wife’s boss got this question three times this year.)

How do I prove that my kids are actually my dependents? Do you need a photo of a messy room?

My dog has a lot of medical bills. Can I claim him as a dependent? {Sure. What’s his social?}

Do I have to report the money I got from jury duty? They did not want to pay me under the table.

I run a moving company. Can I just deduct everything as a moving expense?

What about an aliyah I won in a shul auction?

Wait. US Treasury? I thought I’m paying the IRS!

I am in yeshiva full time, and my rebbi said that a hat and jacket is the uniform of a ben Torah. Can I deduct that as a uniform?

What about my daughters’ school uniforms?

Vhat do you mean vhen you ask me if I have de bentchers? Vhat bentchers? I need to pay tax on my bentchers?

Vhat about my little Mincha/Maarivs?

Can I claim my son-in-law as a dependent, or do the mechutanim get dibs?

If I invited my non-Jewish boss to my child’s wedding to stand around quizzically and wear his yarmulke wrong, can I take the wedding off as a business deduction?

What about my Jewish boss?

Whom do I put as Head of Household—me or my wife?

My son’s rebbi’s wife had a baby, and we all had to get together and buy them a $700 stroller, apparently. Does this at least count as a charitable contribution?

How about that time the school had a campaign and the parents had to raise money on social media platforms we’re officially not supposed to be using, and then I had to kick in 20 bucks so it didn’t look like my friends and relatives weren’t giving anything?

If I adopted a kollel, do I claim it as a dependent? Or 30 dependents?

At what age do you tell a kollel that it’s adopted?

If I’m supporting my son-in-law with money my father-in-law is sending to support me, then what? What do I do?

Wait. Why are we doing last year’s taxes?


Mordechai Schmutter is a freelance writer and a humor columnist for Hamodia and other magazines. He has also published eight books and does stand-up comedy. You can contact him at [email protected].

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