I work in payroll. When a worker wants to have a certain amount of money withheld from their taxes (or not), they have to fill out a form called a W-4 that states how much they want withheld.

In the old days, this was very simple: Workers counted how many dependents they had, wrote down a number based on that, and everybody got either a small refund at the end of the year, or a big one if they had the Child Tax Credit and the Earned Income Credit.

A few years back, we had a president, a guy named Donald Trump, who went and changed the withholding tables. Now you don’t count how many kids you have, you count the number of kids and multiply it by 2,000. You don’t just subtract one if you work another job; you have to calculate for yourself how much to withhold based on how much you expect to make at your other job.

This math is beyond most of our employees.

So then I started constantly getting complaints every April about how people’s refunds were too small.

I mentioned this to the director of the department, and I guess somehow that got everyone sent to a promotional speaker who explained that rich people don’t want refunds, they want to owe the government a small amount of money every year, so they’re not getting an interest-free loan.

I doubt that the interest on a thousand dollars for four months is worth much more than $20, but this got all of our employees fired up. So, they all changed their W-4s again and are now looking forward to owing money at tax time.

We have one employee, let’s call him Kevin. That’s not his name, I just like the way it sounds.

Kevin is 29, married to a woman who’s physically disabled, and has 7 kids with her. Kevin gets a truly gargantuan tax refund every year. Kevin has never before complained to me about his W-4s, or his withholding, or anything else: Kevin has zero federal and zero state withholding.

He does not give the government an interest-free loan of his money, as he doesn’t give them a single dollar of his money.

This year, just like everyone else, he comes in and changes his W4 in the hopes that this will make him owe at the end of the year. He’s excited for it! He wants the extra money in his pocket each paycheck.

Kevin does not notice at the time that his paycheck has not become any larger. His withholding is already zero.

April comes around, and for once, I get almost no complaints about people’s refunds. Everyone either got their Earned Income Credit and Additional Child Tax Credit refund, or owed about a thousand, and was weirdly happy about it.

Not Kevin. Kevin didn’t want a refund. Kevin wanted to go in. Kevin was P***ED.

He called me and complained for hours, calling back when I shut him down for not being productive, that he’d set things up to owe in, that he’d been told that he’d get more money by owing in, that he didn’t see a penny of more money during the year and now he has to suffer the indignity of giving the government an interest free loan?!

My patience is out. I tell him over and over that he’s not prepaid the government anything. I tell him over and over that the motivational speaker was not speaking about his situation. I tell him over and over that with his income and number of children, it’s impossible not to get a massive refund from the government.

Kevin’s been wasting my time for three or four days now, trying to talk me into somehow paying him for his Earned Income Credit and Additional Child Tax Credit in advance on his payroll. I’ve called his manager to explain and get him under control. I’ve called his and my department heads about the situation to try to get someone else to step in. I’ve asked for the duty of repeating these same facts to Kevin over and over to be passed on to someone on his management team, so I can do the god-d*** job I’m actually being paid for instead of arguing on the phone with a moron. Finally, on the recorded line, he utters a threat. “I’m gonna f****** beat you up if you don’t get me my money now.”

I’m exhausted and tired. This is exactly my ticket to no more Kevin.

So I report the threat and have him fired.

Do I feel good about it? No. Has he always been a good worker, up until now? Yes. Does he have seven kids to care for at home? Also yes.

But god-d***-it, it’s my job to make sure everyone working here gets paid correctly, I have about twenty people justifiably riding my a** about overtime pay that vanished into some sort of glitch in the system, which is an emergency, and a hundred more who somehow managed to operate our time system incorrectly and need a clock adjustment, which is not, and a hundred more tasks to complete in order to make sure everyone actually gets paid, all of which are much more important than explaining how taxes and withholding work to a guy who doesn’t want to listen.

Related:
Taxing Taxing, Part 27
Taxing Taxing, Part 26
Taxing Taxing, Part 25
Taxing Taxing, Part 24
Taxing Taxing, Part 23

Unbeknownst to me, the company I used to work for goes under a few months after I quit. I don’t realize this until tax time rolls around and I haven’t gotten my W-2 form, and I look up the company. My wife and I are unsure how to proceed, so we take our forms to a professional to file them for us. It doesn’t go well, and it begins a long, long journey of trying to get our tax refund.

Worker: “I’m sorry, I’m just not sure what you’re looking for?”

Me: “Like I said, the company I worked for last year went under, but they never sent me my W-2, so we need some help filing. I have all of my pay stubs, from the entire time I worked there, but I couldn’t find a way to file online without my W-2.”

Worker: “Uh. Um. Let me… get you my supervisor.”

The supervisor also seems confused after I explain.

Supervisor: “You can just file online. It would be faster.”

Wife: “How do we do that without a W-2? We tried, and the program we were using wouldn’t accept it.”

Me: “I tried filling out a form for a missing W-2, but they wouldn’t accept that either, so we figured we should come to you.”

Supervisor: “That’s odd. Here, I’m going to give you this form to fill out. Use that form, and file online. Since we weren’t much help today, I’m not going to charge you for the visit.”

I don’t remember the exact form he gave us to fill out since this was so long ago, but it was essentially a form that said “yes, I literally do not have a W-2 to file, but I had income”. The Supervisor also explained that we would most likely be audited due to the missing W-2, and to be prepared to wait a few extra weeks for our refund. We thanked him, left, and filed our taxes online successfully using the form.

A few weeks pass, and sure enough, we get a letter from the IRS letting us know they received our tax info, but they needed six more weeks to go over everything. Exactly as we were told, and we breathed a sigh of relief knowing we’d done everything correctly. Until the six weeks pass. Then another six weeks, with no word. I decide to call the IRS helpline to see if I can get an answer.

Me: *angrily jabbing phone off*

Wife: “Did you get someone?”

Me: “No! It’s all automated. Every time I try to ask about what’s going on, it tells me the taxes are being reviewed, then it hangs up. There’s not even an option to talk to an agent, and I can’t find another number to call anywhere. I’m really frustrated, and I want to calm down before I call again.”

Wife: “What about the letter they sent us? Is there a number on there to call?”

Me: “Same number. I just found a way to get a human agent online, but I have to go through a ton of prompts, not answer the last one, and then wait for an agent to pick up. I’m going to do that.”

IRS Agent: “Thank you for calling the IRS, my name is [name], how can I help you?”

Me: “Holy crap it worked. Uh, hi, we got a letter after filing saying that y’all needed six more weeks to go over our taxes, but it’s been double that, and we haven’t heard anything. I was just wondering if we could get an update?”

The phone call doesn’t do much good, but the agent I spoke to put a note in our file that we’d called, assuring us that we should hear from someone soon. And we actually do! Four weeks after the phone call, sixteen weeks after being told to wait just six more weeks, we get a letter from the IRS. Saying that they can’t find any record of the company I worked for, my records do not match, and they need a lot more proof from me to investigate this. I’m also warned that I could be fined for this.

Huh?!

I call the IRS again, doing the long prompts and staying silent at the end to get a human on the phone. But this time, it doesn’t work. As soon as I reach the end of the menu, the instant someone picks up and says “hello”, the line goes dead. I wind up attempting to call over twenty times in one day before giving up. The next day, it worked perfectly the first time.

Me: “Hi, my wife and I filed jointly before the deadline in April. The company I worked for went under and never sent me my W-2, so I had to fill out a form, and we’re being audited. We were told to wait six weeks, but we just got a letter asking for my pay stubs because the company doesn’t exist. Could someone explain what’s going on, please?”

IRS Agent #2: “Please hold one moment while I look into this.” *five minutes of hold music* “Thank you for holding. May I have five more minutes to look into this?” *five more minutes of hold music* “Thank you for your patience. I’ve looked into your file, and I do not see any correspondence from us sent to you. I can only see that you filed in March.”

Me: “That doesn’t make any sense. I called once already, and the agent I spoke to said they left a note in my file since it was taking so long. We were told six weeks, but around week sixteen, we got a letter asking for proof of my pay. Is this not a real letter? Are there no notes about my first call?”

IRS Agent #2: “Do you remember what date you called?”

Me: “It was [date], around four weeks ago.”

IRS Agent #2: “May I place you on a brief hold while I investigate?”

Me: “Sure.”

Ten minutes of hold music, interrupted by the recording of a monotone woman, exasperatedly telling me to file online to avoid problems, the agent comes back. To ask for five more minutes. Five minutes later, he does it again.

IRS Agent #2: “Thank you for holding while I investigated, ma’am. I did find the note left by a previous agent, detailing the phone call you had with them. However, I can’t find any letters we have sent. There was a notice sent out on [date]. Did you get that notice?”

Me: “Um… I think that might be the letter. The one saying they need all my pay stubs on company letterhead to prove my income? Because they can’t find the company?”

IRS Agent #2: “Yes, that is the notice. That is correct. Follow the instructions on that notice.”

So I do. I sent the past year of my pay stubs, downloaded the day before I quit, and waited. About two months after we send the pay stubs in, we get a letter asking for six more weeks to go over all of the information, and we should receive our tax refund shortly after that… IF all of my information matches the information they have. If not, we would have to pay them all kinds of fines.

Then we don’t hear anything for months. It’s not until right before Christmas, nine months after we filed and were told to wait six weeks, that my wife wakes up to find her state tax refund in her account. We do not get mine, nor do we get her federal refund. We get no letters, no calls, no communication about my refund whatsoever. We wait until after the holidays, but I call again at the end of January.

IRS Agent #3: “We sent you a notice in July. Did you receive that notice?”

Me: “Yes, that was the one asking for six more weeks. But that was in July. It’s been much, much longer than six weeks.”

IRS Agent #3: “May I place you on hold while I investigate this?”

Me: “Yes.”

Every five minutes, the agent comes back onto the line to ask for five more minutes. This goes on for an hour.

Me: “Please place me on hold for however long you need to investigate whatever you are investigating. I will hold. You do not need to keep coming back to ask for more time. Just investigate, please. We’re about to file this year’s taxes, and I still haven’t gotten last year’s.”

IRS Agent #3: “Yes. I will place you on a brief hold.”

Me: “Okay.”

IRS Agent #3: *20 minutes later* “Thank you for holding while I investigated, ma’am. I found a notice we sent you in September. Did you get that notice?”

Me: “Yes, I believe that was the notice after the one asking for my pay stubs. It asked for six more weeks. It has been longer than six weeks, and I just want to know what’s going on.”

IRS Agent #3: “I will place a note in your file that you have called.”

Me: *Pause.* “Thank you. Is there anything else you can do? I mean, it’s been almost a year, and the last thing I heard was ‘six more weeks’ for the second time.”

IRS Agent #3: “I’m sorry, ma’am. I agree, it’s strange, but all I can do is leave a note and ask for six weeks to investigate.”

So time passes, and we don’t hear anything. We file our taxes for this year online, with no issues, and get our entire refund with no issue. I even manage to receive my state refund from last year. I call back in July, over one year after that first letter/notice.

Me: “It’s just that it’s been over a year. We got this year’s refund, but we still haven’t gotten last year’s. We haven’t even heard anything since I called in January and left yet another note. Can I speak to someone above you, or have someone call me?”

IRS Agent #4: “I can make a note in your file; however, tax time is incredibly busy. There are delays this year.”

Me: “What do the delays this year have to do with LAST year’s refunds?”

IRS Agent #4: “I’m sorry, ma’am. There is no one here to transfer you to. I will leave a note in your file.”

Finally, my wife gets her federal refund from the previous year! I do not. I have not gotten one bit of communication since I sent in a year’s worth of pay stubs over one year ago. I have recently become physically disabled and am unable to work anymore. Money is tight, and we could really use the refund we’re owed. I call the IRS again, and again it’s the same song and dance of once I finally get someone to pick up the line, the call drops. After two hours of trying, someone answers.

Me: “Hi, my wife has gotten her federal refund, but I have not. I haven’t gotten any calls, any letters, any kind of communication whatsoever. I would like someone to tell me what’s going on.”

IRS Agent #5: “May I place you on a brief hold while I investigate?”

Me: “Yes, and don’t bother coming back in five minutes to ask for more time. Just investigate for however long you need to. I will wait.”

IRS Agent #5: “Thank you for holding, ma’am. I can see that your federal refund was deposited into [account number] on [date]. Is there anything else I can help you with?”

Me: “That was this year’s refund. I’m talking about last year’s.”

IRS Agent #5: “…ma’am?”

Me: “We haven’t gotten LAST year’s refund. This year was just fine. But last year… I don’t know what happened. I never got a W-2, we filed, we sent our pay stubs and proofs that you asked for, I have called so many times, and there have been so many notes left on my file. And we haven’t heard anything, and I just. Can you please, please, just tell me why we haven’t heard anything? At this point, we just need to know. Do we owe you money? Did the company I worked for not exist at all?”

IRS Agent #5: “…let me place you on hold.”

Me: *Dejected.* “Yeah. Okay.”

Insert forty-five minutes of hold music interrupted by that same monotone woman explaining how to use the online tools. I’ve started hearing her in my nightmares.

IRS Agent #5: “Ma’am, I am so sorry about this. I don’t know what happened either. If there were someone here above me, I would ask them, but there is not. I looked over your entire file, and you are correct. This is strange. I am sorry this is happening, and I will do what I can to assist, but I need to ask for six more weeks to investigate this.”

Me: *Bursts into tears and hangs up.*

I have fully given up at this point. The money is either gone, never existed in the first place, or I actually just owe them money. I decide I’m not going to call them again, I’m just going to wait for them to reach out to me. Christmas comes and goes again. We prepare and file our taxes in the new year. It has been over two full calendar years since it all started. It’s been over a year since I called the IRS the last time and was asked for six more weeks.

And then, right around Thanksgiving, I get a letter with a check. On the check is a number higher than the refund I never got. The letter is from the IRS… apologizing. Apparently, there was NO REASON it took that long to review my pay stubs and send me my refund. My records matched their records, they had my old company on file, and everything wrapped up neatly. So, I was getting interest on the refund, as well as an apology, and the matter finally- FINALLY!- closed almost three years later.

Way back when I first started as an accountant, I had a client get upset with me because I wouldn’t let her claim her twenty-two-year-old son.

She and her husband (who behaved as a non-entity this whole conversation) made $500,000 per year between the two of them, and she was responsible for about $350,000 of that.

Her son was out of college, made $100,000 per year, and didn’t live with them.

I asked all the questions:

Me: “Is he disabled?”

Me: “Does he live with you?”

Me: “How much does he make?”

Me: “Is he in college?”

Each answer pointed to them not being able to claim him on their taxes. Finally, I told them flat out:

Me: “You cannot claim him on your taxes.”

Client: *Extremely upset.* “I wanted you to cite a specific passage in tax law saying that my son can’t be claimed!”

Me: “There isn’t a specific passage; there are about six passages scattered across four different sections.”

I showed her individual passages individually, but as soon as a passage wasn’t in her sight, she forgot about it, and she couldn’t connect the different definitions of ‘claimed’ and ‘dependent’ together in her head. She kept pointing to tangents that did not count for her situation, like ‘still in college’ or ‘disabled’ or ‘lived with and provided more than half of the support’ or ‘divorced parents splitting the child’. We kept going in circles, and it made me later and later for my next client, who had arrived.

Finally, I had an outburst:

Me: “Look. I’m the tax accountant here. I was trained for this. You clearly were not, and you obviously are failing to understand. I was trained in this; you are not. I understand this, you don’t. You can’t claim your son. Either sign and pay for your taxes or leave.”

Grudgingly, they signed and paid for their taxes. They complained to my district general manager about it, and I got a write-up.

Years later, I’m an enrolled agent and running my own accounting firm that specializes in taxes. I have partners (employees I granted ~2% ownership so we can be less unequal because I suffered so much trauma from typical corporate structures and didn’t want to inflict that upon others) who prefer to take the less complicated clients and I get to focus on the more complicated ones who are more fun to do (and who my partners hate to do).

One of my former managers is a 20% partner; she helped to pay in at the very start, and she mans the receptionist desk for us all: A skill she is extremely good at.

I get a client, a young man. I take him on because he has a lot of really fun and crunchy investments… five K1s, some crypto, a few straddles, some rental real estate properties, an oil well in North Dakota, even a farm plot in Wisconsin he’s sharecropping out. This is serious fun. I’m honestly considering giving him a discount just because I’m having so much fun. I’ve never quite understood why my partners prefer to do easy returns.

He’s also barely twenty-one, he makes about $120,000 per year at his W2 job, and he’s still in college.

He tells me his parents want to claim him as a dependent, but he fairly obviously doesn’t count as a dependent: He clearly provides more than half of his own support. I ask him all the questions:

Me: “Who pays for your apartment?”

Me: “Who pays for your entertainment?”

Me: “Who pays for your food?”

Me: “Who pays for your college?”

I explain that he has to claim himself: None of the answers he gave me indicate that his parents are permitted to claim his exemption.

So, he calls his parents. They come in. They make a big show of it; they roll up in a god-d*** white limo.

These parents make $750,000 between them in their W2 jobs. That’s before their myriad investments.

Parents: “Provide citations showing our son can’t be claimed as a dependent.”

This time, I just shrug and very openly delete his return-in-progress, delete our stored scans of the tax documents, then hand the son back all of his original documents.

They spluttered at me, flabbergasted.

Me: “Was that all?”

Mother: “What… why are you…”

Me: “I’m refusing you service. You’re denying my basic competency in one of the basic aspects of taxation: Determining dependency. If you were questioning me about something like state allocation of K1 income, or the exact handling of non-cash distributions, or something like that, I would have been more than happy to hand you a citation. I do that all the time for IRS agents who don’t know the law as well as I do. But this? No. This is too basic and foundational. This is a statement that you don’t trust me to do your son’s taxes. And that’s fine. Have a nice day.”

She started yelling at that point, that she would complain to my manager, laced with a few profanities, but my wonderful receptionist was standing by the door. She opened it up, let them believe she was the manager, and ushered them out. They left.

Later, the parents called me to complain. I just muttered:

Me: “Oh, it’s you two f***ers.”

I snorted a quick laugh and hung up.

I f****** love being self-employed.

I do taxes for a living. A client owes some money to the IRS, about two hundred dollars. She’s an older woman, she owed last year as well, nothing about this should be a surprise or abnormal for her.

Me: “How do you want to pay the IRS?”

Client: “Can I mail them a check?”

Me: “Yes. Let me print up for you a slip sheet and a voucher.”

I put the slip sheet in the envelope so that the address shows through the little plastic window, clip the voucher to the side with a paperclip, and tell her to mail the check and voucher to the IRS in the envelope.

A few weeks later, she comes back mad as h***.

Client: “The IRS returned the check! You must have done something wrong! Now I’m going to have a late penalty.”

She dramatically throws the returned, still sealed, envelope down onto my desk. I glance over it and notice immediately what went wrong: She’d inserted the check so that it covered up the IRS’s address in the window on the envelope.

I let her rant at me for a bit until she felt better, then I got another envelope from the back, gently opened the one that the post office (not the IRS) returned, moved the slip sheet, voucher, and check into the new envelope so that the destination address was clearly visible through the window, resealed it, wrote her return address on it, and handed it to her.

Me: “Should work now. Make sure to put a fresh stamp on it.”

Client: “Good. Don’t let this happen again in the future, or I shan’t be returning.”

Me: “Okay. Have a nice night.”

And she left, not to darken my door until next year.

Client: “Before we get started, I’ve got a question for you.”

Me: “Go ahead.”

Client: “I just got married…”

Me: “Last year, or since New Year’s?”

Client: “Last year.”

Me: “Okay.”

Client: “My spouse doesn’t make any money.”

Me: “Is she disabled?”

Client: “No.”

Me: “Okay.”

Client: “Can I claim my spouse as a dependent?”

Me: “Since you’re legally married, as of December 31st, you’re considered married for the full year.”

Client: “Okay.”

Me: “As such, you can do something better than claiming your spouse as a dependent. You can claim your spouse as a spouse, and file jointly.”

Client: “What does that mean?”

Me: “Well, first it means I’m going to need to have your spouse come in and sign your taxes too.”

Client: “Can we file without her?”

Me: “Yes, but you’re not going to want to.”

Client: “Why not?”

Me: “As a married person, you have to choose between two, technically three, filling statuses, and one of them is terrible. The other two are pretty great, but you don’t qualify for one of them.”

Client: “Why don’t I qualify?”

Me: “Did you live with your spouse any day in the last six months of the year?”

Client: “Yes.” *With a ‘duh’ look.*

Me: “So you can’t file head of household.”

Client: “What’s head of household?”

Me: “A side track, I’ll explain that to you after I explain Married Filing Joint.”

Client: “Okay.”

Me: “Married filing joint lets you and your spouse add your income together and be taxed in a lower tax bracket as a result.”

Client: “What does that mean?”

Me: “It’s difficult to explain, and it’s easier to simply show. In essence, you’ll be taxed at a lower rate than you otherwise would be for every dollar of your income. The more different your and your spouse’s income is, the more money you save. Since she doesn’t have any income, you’re going to save a lot. Can I put your taxes together and show you what the different filing statuses do to your taxes?”

Client: “Okay.”

I do the taxes and show the difference.

Client: “Wow, that’s great! I want that one! That’s the one I want! Can we finish now?”

Me: “Unfortunately, I still need your spouse’s signatures. If you want, you both can come in to sign together, or you can sign now, and your spouse can come in to sign later.”

The client leaves happy, but unfinished.

Next Client: “Before we get started, I’ve got a question got you.”

Me: “Go ahead.”

Next Client: “I just got married…”

This conversation is so common that I once had this exact same conversation five times in a row, practically word for word.

There’s about a one in three chance their spouse will come back on their own to sign, and a two in three chance I need to call the client in April and remind them that we still need signatures. Male clients need to be called slightly more often than female clients. Same sex partners need to be called for a reminder much less often than opposite sex partners.

Initially, interrupting the client to ask the year and if the spouse is disabled is deliberate, as it gets the client in the mindset to listen to me. If I don’t do that, it doesn’t work as well.

Deliberately pausing for the client to interrupt me and for the client to say “okay” also sets up the flow.

Related:
Taxing Taxing, Part 26
Taxing Taxing, Part 25
Taxing Taxing, Part 24
Taxing Taxing, Part 23
Taxing Taxing, Part 22