AI and the Tax Man


It was April 14th, 2025, and Jerry Jenkins, a freelance kazoo musician with a side hustle selling artisanal lint sculptures, was blissfully unaware of the storm brewing on the horizon. Jerry lived in a cluttered apartment where receipts grew like mold, and his idea of “filing taxes” was tossing W-2s into a shoebox labeled “Yawn Stuff.” But this year, the tax deadline—April 15th—had plans to make Jerry its personal piñata.

The trouble started when Jerry’s best friend, Marge, a part-time astrologer and full-time chaos magnet, burst through his door waving a horoscope. “Jerry! Mercury’s in retrograde, and Venus is doing the cha-cha with Pluto! You have to file your taxes before midnight tomorrow, or the IRS will haunt your dreams!”

Jerry scoffed, sipping a kale smoothie that tasted like regret. “Taxes? Pfft. I’ll do ‘em next week. The government loves a procrastinator. Builds character.”

Marge’s eyes widened. “Jerry, the IRS doesn’t build character. It builds liens. You’ve got one day!”

Panicked, Jerry dove into his shoebox like a pirate hunting treasure, only to find a receipt for “17 pounds of glitter” (a lint sculpture experiment gone wrong), a napkin with “DEDUCT THIS?” scrawled in ketchup, and a coupon for free tacos. No W-2s. No 1099s. Just vibes and existential dread.

“Relax,” Jerry said, mostly to himself. “I’ll use one of those tax apps. They’re like video games, right? TurboTax, more like TurboFun!” He downloaded the app, but it demanded numbers—numbers Jerry didn’t have. “What’s a Schedule C? Sounds like a bus route.” The app’s chatbot, a smug AI named TaxBot3000, wasn’t amused. “Input gross income or face penalties,” it droned. Jerry typed “vibes?” TaxBot3000 logged off in disgust.

By 10 p.m., Jerry was sweating. He called his cousin, Lenny, a CPA who moonlighted as a conspiracy theorist. “Lenny, help! What’s a deduction?”

Lenny whispered through the phone, “Deductions are the government’s way of testing your loyalty. Claim your kazoo reeds, but not the glitter. They’re watching the glitter.” Before Jerry could ask more, Lenny hung up, muttering about Area 51.

Desperate, Jerry sprinted to the 24-hour library, where a librarian named Agnes, who looked like she’d audited God’s books, took pity on him. “Kid, you’re a mess,” she said, handing him a tax guide thicker than his mattress. “Read fast.”

Jerry flipped through pages, learning words like “amortization” and “withholding,” which sounded like a medieval torture method. He scribbled numbers on a legal pad, claiming deductions for “emotional distress from tax season” and “kazoo-related tinnitus.” Agnes sighed. “You can’t deduct vibes, Jerry.”

By dawn on April 15th, Jerry’s apartment looked like a paper tornado had hit. He’d found one W-2 behind his fridge, calculated his income (mostly vibes, some dollars), and e-filed at 11:59 p.m., seconds before the deadline. The confirmation email felt like a Nobel Prize.

Exhausted, Jerry collapsed on his couch, only to hear a knock. It was Marge, holding a taco. “You did it, right? Mercury’s proud.”

Jerry grinned. “Yeah, and I’m never doing taxes again.”

Marge laughed. “See you next April, champ.”

And somewhere, TaxBot3000 shed a single digital tear.


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