THE DAY I TRIED FILING TAXES MYSELF AND IMMEDIATELY REGRETTED IT
THE DAY I TRIED FILING TAXES MYSELF AND IMMEDIATELY REGRETTED IT
I woke up one morning with the boldness of a man who had watched three YouTube videos on financial literacy and felt unstoppable. It was tax season, and as someone who had been hearing words like “financial independence,” “wealth management,” and “smart money habits,” I decided that filing my taxes myself would be the moment I finally reclaimed my financial power.
But the universe had other plans.
. Because the moment I opened the IRS website, the page looked like a crossword puzzle designed by a stressed accountant who wanted revenge on the entire population. I literally blinked twice, expecting the site to transform into something simpler. Instead, the IRS homepage stared back at me like, “Welcome. Enter at your own risk.”
And I foolishly entered.
I began the process fully ready to exhibit the financial intelligence of an investment expert. I had my ID, employment details, bank statements, and emotional stability — or so I thought. The first question asked me something about “filing status,” and suddenly, my confidence evaporated faster than my bank account after an impulse online shopping spree.
Single? Yes.
Head of household? Possibly.
Qualifying widower? Definitely not — but the fact that the form made me consider it for two seconds worried me deeply.
At that moment, I realized tax filing was not just paperwork. It was psychological warfare.
The next page asked me to enter my annual income. I typed the number slowly, as if the IRS would judge me. The moment I hit enter, the website acted like I had confessed a crime. It started generating forms like it was printing receipts for a billionaire.
W-2.
1099-NEC.
1099-MISC.
Form 1040.
Schedule A.
Schedule C.
Schedule ‘You Are Officially Finished.’
I stared at the list in horror and realized these forms were multiplying like rabbits on a high-protein diet. Every time I clicked something, three more forms appeared. It was like financial hydra — cut one, two more grow.
At this point, I briefly considered hiring a tax professional. But when I saw “tax preparation fee: $280,” I decided financial responsibility meant suffering alone. I had already Googled phrases like “How to legally disappear before tax day” and “Countries without tax requirements for confused citizens,” but Google kindly suggested, “Please file your taxes. Running is not a financial strategy.”
So I continued.
I tried entering my deductions next. That was my biggest mistake.
Why does the IRS expect people to know whether something is “tax-deductible” when half of us can’t even decide what to eat for dinner? I began adding everything I could think of — groceries, rent, toothpaste, emotional damage, Wi-Fi stress, the cost of my sanity — but the little “i” information icon kept telling me politely, “No, absolutely not.”
Apparently, according to the IRS, nothing in life is deductible except suffering.
Then came the question that broke me: “Did you make any contributions to a retirement account?” I stared at the screen for a full minute, wondering if the IRS meant emotionally or financially, because financially? Definitely not. Emotionally? Every day.
As if the torture wasn’t enough, the tax software tried to upsell me “Premium Tax Assistance” for an extra $129. It promised audit protection, financial guidance, and “exclusive tax insights,” which sounded suspiciously like therapy for people who cry during tax season.
I declined.
Proudly.
And then instantly regretted it.
Because the moment I clicked “no,” the website started behaving like a disappointed parent. It took longer to load. It glitched. At a point, I’m certain my laptop whispered, “You should have bought the premium package.”
When I got to the section about “business income,” I made the mistake of listing my tiny side hustle — which barely generates enough income to buy a medium-sized pizza — and suddenly the IRS assumed I owned Amazon.
It started asking me questions about “business assets,” “capital depreciation,” and “operational expenses.” I panicked because my only “business asset” was a second-hand laptop that sounds like a helicopter when it overheats.
Then it asked, “Do you have employees?”
Employees?
I can barely afford myself.
My stress level was now higher than the national debt. Every financial keyword in existence was attacking me on the screen: “taxable income,” “adjusted gross income,” “capital gains,” “self-employment tax,” “itemized deductions,” “investment returns,” “tax credits.”
I was sweating like someone being interrogated for a crime they didn’t commit but might confess to anyway just to go home.
Finally — after 90 minutes of clicking, typing, deleting, re-typing, Googling, and reconsidering all my life decisions — I got to the final page. The summary.
This was the moment I had been waiting for.
The moment of truth.
The page loaded dramatically, like a season finale. Then it displayed a number so disrespectful I felt personally offended.
My refund: $4.89.
Four dollars.
Eighty-nine cents.
Not even enough to buy a burger. Not even enough for premium YouTube. Not even enough for tax software to respect me.
I reloaded the page, expecting the number to grow out of pity. It didn’t.
Then the software had the audacity — the pure boldness — to show me a notification:
“Tip your tax specialist?”
Tip who?!
Tip myself for the emotional trauma I just experienced?
I almost threw my laptop.
But the suffering wasn’t over.
Because below the refund amount was another line that read:
“Processing fee: $5.”
Meaning I now owed THEM eleven cents.
I went from expecting a tax refund to financing the IRS with pocket change.
I stared at the screen with the type of silence you only hear in movies before a main character goes completely insane. This tax software had taken my time, my dignity, and my false hope, then charged me for the experience.
By the time I clicked “Submit Return,” I felt spiritually exhausted. I had aged 10 years. My soul left my body and came back only to laugh at me.
I closed my laptop gently because I knew if I slammed it, the IRS would sense the aggression and audit me out of spite.
Then I lay on the bed and stared at the ceiling, whispering,
“Never again. Never ever again.”
As I recovered, I realized something important: tax filing is the world’s most effective psychological test. It measures emotional durability, financial awareness, and your ability to read sentences written in advanced accountant language.
It showed me that true financial literacy isn’t about stock investments, passive income, or personal finance strategies — it’s about surviving tax season without crying into a pillow.
The next time tax season comes around, I will cheerfully hand $280 to a tax professional with the same energy I use to pay for streaming services. Because peace of mind is a taxable commodity, and I’ve learned the hard way that I can’t budget my way out of IRS-level stress.
And that is the story of how I filed my taxes once, suffered greatly, and realized that maturity has nothing to do with age — it begins the moment you stop pretending you understand tax forms.
Financial freedom is beautiful, but tax season?
Tax season is a horror movie wrapped in accounting terminology.
The lesson?
Just hire someone.
Your mental health is not tax deductible.
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