#TaxStories – Real Tales from the Tax Desk:
After a decade of preparing taxes commercially, I’ve finally compiled all my stories in one place. These are real experiences I’ve encountered over the past 10 years—shared with names and locations withheld to protect privacy.
Each story is presented for educational purposes only, offering insight into the wild, unpredictable, and often eye-opening world of tax preparation. Whether you're a taxpayer, a business owner, or a fellow professional, I hope you find these lessons as enlightening—and sometimes entertaining—as I did living them.
1. “Lo Barato Sale Caro” — The $100 Tax Prep That Really Cost $775
This one is borrowed from a fellow tax pro, but I’ve seen it too many times myself. A client once told me he’d been paying only $100 cash for tax prep and always got direct deposit. I offered to review his prior return—confident, not cocky. And guess what? His “$100” return actually cost him $775!
Here’s how: $675 was quietly taken out through a refund transfer product, and then the $100 cash on top of that. This was never disclosed to him—and it had been happening for five years. Sadly, this kind of unethical and illegal practice still happens. When you hire me, you’re paying for my education, credentials, insurance, and peace of mind that your return is 100% within the law. I’m not Dollar Tree. I’m not Walmart. I’m Target. 🎯
2. DIY Disasters Still Haunt Me
Even years after leaving my old tax firm, people still call asking for help cleaning up their TurboTax mess. There’s nothing wrong with doing it yourself—until it goes wrong. 😅
3. Estimated ≠ Exact
That $12,000 refund estimate you saw online? It’s called an estimate for a reason. You’re still getting $9,000 back! I know plenty of people who’d jump at that. Just a reminder: Don’t focus on what could have been, focus on the fact that you’re still getting money back.
4. Adopting a Dog ≠ Tax Deduction
Yes, a client really tried to deduct their dog’s adoption fee on their tax return. Nice try… but no. 😂🐶
5. Business Loss ≠ Tax Skip
One client decided to skip reporting his business because “it wasn’t making money.” His wife asked me to take a look. Turns out, he had left plenty of deductions on the table. After properly including everything, I increased their refund by $1,000. Just because your business isn’t profitable doesn’t mean it’s not worth reporting—sometimes it saves you more than you think. 💸
6. Magic in the Margins: $6,500 Refund
After some solid tax planning and strategy, a household making close to $120K got a refund of nearly $6,500. Yes, it’s possible—with the right preparation and a little tax magic 🧙🏽♀️✨
7. Why Do We Owe?!
Couple with two kids, made $100K, and only had $1,500 withheld for taxes. They were shocked to learn they owed. “But the online calculator showed a refund!” Yes… until reality set in. 😵💫🤣 It’s not magic. It’s math.
8. $100 in Tax Withheld on $23K Income = You Owe
Single, no kids, $23K income, and only $100 in tax withheld. Yep, you owe. But instead of getting upset, this client said, “Can I do a payment plan?” Educated, paid, and left happy knowing what to do differently next year. That’s the goal!
9. Commuting to College? Not Deductible.
No, you can’t write off the gas you use to drive to college. Sorry. 🤦🏼♀️
10. Refund Boost from a Quick Review
Found 💸💸💸 hiding in a client’s refund just because something wasn’t filed properly. Corrected it, and the result? A much bigger refund. Nothing beats that feeling of helping someone keep more of their money.
11. Bathrobe & Boots—Tax-Ready
A client once showed up to do her taxes in a bathrobe and boots. Who said that look was exclusive to Wally World? 😂
12. Tickle Me Elmo Vibes at My Desk
A young man came in and couldn’t stop laughing—like full-body jiggles. Every line ended in a giggle: “I’m single (jiggles), I have a W2 (jiggles), I live in Florida (jiggles).” I wasn’t sure if he was nervous, high, or auditioning to be the next Tickle Me Elmo. 🧸
13. DITY Confusion
A young couple came in with only a DITY W-2. I asked for the military pay W-2. The husband replied, “That’s the only one they mailed me.” I said, “Check MyPay.” He looked at me like I spoke a foreign language. 🤦🏽♀️ Military folks, please check your LES and MyPay before tax appointments!
14. Charged $20 Just to Walk Away
Middle-aged couple stopped by after walking out of a big-name tax place that quoted them $600—and still charged $20 just to leave! They came to me, and not only did we file for $325, but they ended up getting $7,500 back instead of the $6,202 originally quoted. Better service, better outcome.
15. Do 👏 Not 👏 Lie 👏 on Your Taxes
In just four weeks, I’ve seen six clients receive IRS letters demanding thousands back—because they lied on their tax returns. Yes, the IRS does check. Fraud may get past software, but it won’t get past the IRS forever. The truth always costs less than the consequences. 💸
16. #HeckNo List: Activated
Client came in on a day I wasn’t working and pretended he forgot paperwork just to book a one-on-one. I had taken an Uber with him three years ago. Now he asks about my hair color, marriage, and emotional well-being. Note to self: start a “Do Not Schedule” list. 😳 #TaxPrepNotTinder
17. Receipts ≠ Deductions
Client brings in an envelope full of receipts: grooming, clothes, random work items. When asked why, he said, “I always used TurboTax when I was single.” His wife immediately turned to him and said, “TOLD YA!” We couldn’t use any of them. But at least he got a free tax education with the appointment. 😅
18. Scratch-Offs Are Not School Donations
Yes, a client tried to deduct lottery ticket losses as charitable donations to education. 😑 I wish I were making this up. Up next: people trying to claim the teacher credit for their kids' virtual learning setups… 🫠 #YouTried
19. Ignoring IRS Letters = Instant Audit
Some people think if they ignore IRS letters, they’ll just go away. Spoiler: they won’t. Once you’re on their radar, they will keep looking. And please—stop changing your filing status every year. Married, single, HoH, back to MFS… all while still living with your spouse. That’s a red flag parade.
20. Cursing Won’t Fix Missing Documents
A client got married and tried to file jointly—but had no documents for his new spouse or her child. When I explained I needed insurance coverage forms (1095) for everyone, he refused to involve her ex and… well… let’s just say the F-bombs started flying. He kicked over my trash can and stormed out. #NotMyFault
21. Retail or OnlyFans? Depends on Who’s Listening
A newlywed couple sits down. Wife says her income is from “retail sales online.” Husband steps away… and she says, “Actually, it’s OnlyFans.” 😅 Then asks how to deduct expenses. I told her: boxes of receipts won’t cut it, but we can still file correctly. No judgment—just facts.
22. Find Me the Trump Loophole?
Client: “Can you find me the same loophole Trump used so I don’t have to pay taxes?”
Me: 🤨🤣
23. Texting Tax Docs? Please Don’t.
Client wanted to text me her tax documents so I could email them… to myself. Same person found me on Facebook and started sending messages until she was permanently blocked. Meanwhile, I now have 200 pages of crypto trades to enter. 😖 Pray for me.
24. Online Tax Regret Is a Common Theme
Almost every appointment starts with:
“I tried doing it online but…”
– “I messed it up.”
– “It doesn’t look right.”
– “I went to the tax center on post.”
Every. Single. Year.
25. Oops… That’s Not Your Husband’s Return
Wife dropped off her docs and noted she was going through a divorce but still filing jointly. Husband shows up later and finds another man’s tax return in her paperwork… Let’s just say the appointment did not end well. 😬 #PlotTwist
26. Cooking the Refund
Client said she “adjusted” numbers to make the refund reach a certain amount—because it felt right. I fixed it. The right refund isn’t about what feels good—it’s about what’s legal. 😅
27. We Don’t Run on Tokyo Time
Client missed his appointment and insisted it was 9am Saturday.
Me: “Your appointment was 4pm Friday—Central Time.”
Client: “But it’s Saturday in Japan.”
Me: “Sir… we don’t set appointments based on Japan time.”
🤦🏼♀️ I’m not syncing with every global timezone.
28. TikTok ≠ Tax Code
Someone told me they saw a “new law” online that said you don’t need to file business taxes if you made under $100K.
Where did they see this? TikTok.
Please—just no. 🙄
29. W-2 Box = Refund?
Client: “Which box on the W-2 shows how much I’m getting back?”
Me: “None of them. That’s… not how this works.”
🤯🤣
30. IRS Letter: You Owe $30K 💔
Getting an IRS letter saying you owe $30,000 is… intense. I’m just glad I could help bring that number down and walk the client through it. This is why professional help matters.
31. Breaking Bad Meets the IRS
Client came in to amend his return. Claimed he “cooks meth” and wanted to fix his taxes discreetly. Said he was military, worked part time, and should be exempt from taxes altogether. 😵💫
Y’all… I need a weekend off.
32. “When Do I Stop Filing Taxes?”
Client: “When do I stop filing taxes?”
Me: “When you die. But someone will still file one last time for you.”
💀
33. Dump Truck for Rentals?
Taxpayer: “I bought a dump truck to haul gravel into my rental properties. That’s a write-off, right?”
Me: 🫣😶🙄
Sometimes the questions are funnier than the answers.
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