Pentwater — April is here. We whisper to ourselves that, “It’s going to be okay.” Then, out of the blue, we get kicked in the teeth. April 15th. Tax day.
This dastardly day of public misery and government-induced annoyance always sneaks up on us. Tax Day is an irritation for every right-thinking citizen. No one likes it, and because everyone dreads it, we all collectively forget about it until two weeks before.
But all is not lost. There is a cure to our collective American pain, a remedy that helps the taxation medicine go down a little easier: the tax extension.
Filing a tax extension is a quick and easy hack for a happier life, or at least a happier spring. Pretty much everyone can do it. It takes about five minutes, and it delays that bureaucratic pain until October 15th.
A naysayer may claim that it’s better to get it all over with, that delaying until October is pointless. They are wrong. It’s this kind of NPC thinking that leads to a life of quiet misery, turning oneself over completely to the system, embracing Tax Day as a friend and not a foe. It’s practically un-American.
“I love Tax Day! I get money back on my return, and I can use it to buy something nice!” This is a sentiment many Americans naively profess.
Why is it naive? Because the only sad saps who feel this way are W-2 workers who have taxes automatically withheld and don’t really realize how much they are really losing every paycheck. They might see the number, but they don’t really feel the number. They never had it, so they never lost it. They don’t realize how much they pay in taxes.
When you’ve got someone skimming 10 French fries off your plate back in the kitchen, you feel like you just got a great gift when they give two “extra” French fries on a random Tuesday in April.
“Gee whiz! Thanks a lot,” the grateful dupe says as he gobbles up his little treats.
If more people were self-employed, more people would be concerned about where their tax dollars were going, simply because they would feel the pain of taxation more accurately. In the distant American past, most people were either self-employed or small business owners. It’s no coincidence that as fewer and fewer people earn their living as self-employed individuals or small business owners, taxation has increased.
Tax Day is only properly understood by the self-employed individual or small-business owner. It is only he who feels the pain properly, only he who can see the reality clearly. He builds on his own, continues forward with no safety net, creating, innovating, providing. He embodies the American spirit. The one that sailed across the sea and settled the West. He moves the world forward.
And what does he receive in return? A big bill from the government.
That’s the state of the world in 2025. We’ve all got to pay our bills, we’ve all got to pay our taxes. We can’t get around it, but the least we can do is delay the pain until autumn. After a nice summer, the pain of taxation is a bit more palatable. Putting off the irritating reality of taxation for just a few months feels like some kind of mini-resistance or hesitation.
Paying your taxes is part of being a good citizen, but resistance to taxation is part of being an American. These two ideas are not at odds with one another. They can be brought together.
Be a patriot: File a tax extension.
O.W. Root is a writer based in Northern Michigan, with a focus on nature, food, style, and culture. Follow him on X @NecktieSalvage.
