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 3.5-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?”
I mean imagine that Hashem said, “Everyone needs to do teshuvah by Rosh Hashana,” and then everyone woke up in that last month. Half of us would have to file extensions for Yom Kippur.
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, because I need my wife to keep her job, for tax reasons, 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?”
I ask as someone who is constantly wondering if I could take everything in my life off as a deduction, if at some point I write about it. And I write about everything. But I’m not going to ask that now, because it’s clearly not a good time.
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?
- How do I make sure my boss sends me the tax forms?
- 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?
- What if I live on a houseboat, then… then… What do I do? {This sounds like a Hilchos Shabbos question.}
- My boss sent me a w-2, but I still haven’t gotten my w-1. Should I let him know?
- Who’s your accountant? Like when you have a shaylah?
- When you say you need my ten ninety-nine, is that ten ninety-nine plus tax?
- If I keep my receipts in a shoebox, can I deduct the cost of the shoes?
- Um… How many kids did I claim last year?
- I want to save money on taxes in the future. Should I just make less?
- Is there a way to get through an entire year using only third-party checks? Like some sort of dina d’Rav Nosson?
- 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 3 times this year.)
- How do I prove that my kids are actually my dependents? Do you need a photo of a messy room?
- So do you just use Turbotax, or what?
- Is something considered a home improvement if I did it myself and it doesn’t quite work?
- My dog has a lot of medical bills. Can I claim him as a dependent? {Sure. What’s his social?}
- Can I send my son a w-2 for his allowance if the total was over $600? I’m trying to teach him responsibility.
- 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?
- I had to move for business. Can I deduct the cost of moving my pet? It got pretty sick on the plane.
- 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 white shirts at least?
- What about my daughters’ school uniforms?
- How can I tell if I have cryptocurrency? Like what does it look like?
- 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 take off day camp as a child-care deduction if I also work in that day camp?
- What if I’m my son’s learning rebbi? Still?
- Then why doesn’t everyone do it?
- 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?
- Should I itemize my children?
- A short while back, someone offered to buy my house via postcard, sight unseen, and I agreed. But I haven’t seen the money yet. What year does this go on?
- 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 kick in 20 bucks so it didn’t look like my friends and relatives weren’t giving anything?
- What about the phone I had to buy to do this?
- If I adopted a kollel, do I claim it as a dependent? Or 30 dependents?
- This is not a tax question, but 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?
- If I owe my state money and am also getting a refund from the federal government, shouldn’t they just pay each other and leave me out of this?
- Wait. Why are we doing last year’s taxes?
Mordechai Schmutter is a weekly humor columnist for Hamodia, a monthly humor columnist, and has written six books, all published by Israel Book Shop. He also does freelance writing for hire. You can send any questions, comments, or ideas to This email address is being protected from spambots. You need JavaScript enabled to view it.
