If I Cry While E-Filing, Is It Still a Business Expense?
Today is Tax Day. April 15. The day when printers jam, browsers crash, and every adult in America becomes a freelance accountant with trust issues.
It’s no-one here. And I’ve been thinking — not just about line 37b or whether you saved that one freelancer receipt from February — but about the strange emotional toll this whole thing takes.
Seriously, if I cry while e-filing, is it still a business expense?
Probably not. But it should be.
Let’s talk about what makes Tax Day so infuriating, so unavoidably personal, and just a little bit poetic.
When Income Feels Like Confession
Tax Day isn’t just a financial deadline. It’s a personal inquisition.
It’s the system saying:
“Hello. We noticed you participated in the economy last year. Please prove it. In triplicate.”
Every form is a passive-aggressive puzzle.
Every instruction is written like someone trying to be helpful while also holding a grudge.
And every deduction feels like it was invented just to make you doubt your own life choices.
People hate Tax Day for all kinds of reasons — the paperwork, the panic, the possibility that you’ll forget something that ends in a letter and a number like “1099-NEC” — but mostly, they hate the vulnerability of it.
Tax Day is adulthood’s annual performance review.
It’s what you made, what you saved, and what you now owe — stripped of context, emotion, or nuance.
It doesn’t care about inflation.
It doesn’t care that your dog needed emergency surgery.
It just wants you to scroll to the bottom of the form and click “submit” while quietly sweating.
Quickfire Notes From the Edge of the Fiscal Abyss
- “Free File” is basically an emotional bait-and-switch.
- The IRS refund tracker is a Magic 8 ball that says “still processing.”
- There's always one W-2 you forgot from that three-week side hustle.
- Tax software is the only app that gaslights you and charges you for it.
- You will panic-Google “can you write off coffee?”
- Post offices on April 15 feel like the DMV and an escape room had a baby.
- If a form says “See Schedule 3,” and Schedule 3 says “Refer to Line 14,” you are now in a Netflix plot twist.
- At least one person today will scream at a printer like it’s a tax agent.
This Newsletter Is Not Tax-Deductible
Why talk about Tax Day here, in a newsletter that’s usually about odd questions and AI musings?
Because Tax Day is one of the most human days of the year. It’s full of contradiction:
You’re overwhelmed but expected to be precise.
You’re being squeezed for details, but no one’s really explaining why.
You’re asked to be honest in a system designed around loopholes.
Outsourced to AI is a place to hold a mirror up to these strange, shared experiences — not to fix them, but to name them. And maybe to laugh at them a little. Because if we can’t laugh at Tax Day, we’ll probably just cry… and then try to write it off.
🌒 Final Note:
If you’ve filed already: you’re a hero.
If you’re filing now: stay strong, hydrate.
If you’re filing tomorrow: good luck explaining that timestamp.
Whether or not the IRS counts it, emotional damage should be deductible.