I love winter. I love snow. I love making a roaring fire in my fireplace on a chilly day. But I hate one thing about this time of year: taxes.

February is rough for the self-employed. It’s rough because my 1099 forms - official records of how much my clients paid me last year - arrive in the mail.  

As the 1099s roll in, I hope and pray I made less than I know I did - because my tax “contributions” are always way more than I thought they would be.  

I’d like to meet the genius who used ”contribution” in place of “mandatory tax liability.” He’s probably the same guy who calls our nearly $28 trillion national debt an “investment.”

As a former English major, I’ve never been fond of math and accounting. But from February through April 15, tax day, I have to do my best at both. 

That’s because our income tax system is complex. It’s complex because drunk people (members of Congress) designed it so that a bureaucracy (the IRS) converts the incomprehensible (tax law) into the unfathomable (complex tax regulations) to punish productive Americans (the self-employed), all in the name of good fun.

I hire a certified public accountant to calculate my tax contributions. But my CPA makes me sort and tally all of my expenses first.  

From Jan. 1 through Dec. 31, I toss every bill, receipt, expense, etc., into a large cardboard box - because these little slips of paper, which are deductions against my tax burden, are like currency to me.

Beginning in February, I spend hours sorting through last year’s slips with one goal in mind: to get my earnings from the prior year as low as legally possible, so my income tax bill doesn’t give me a heart attack, which I cannot afford anymore because my “self-employed health insurance policy” has a deductible that’s soared higher than the value of my 2020 Toyota Tacoma!  

About this time every year, I curse Republicans, who have talked about simplifying the tax system throughout my adult life.

“Vote us into power and the tax code is the first thing we’re going to fix!” they always promise. 

“You’ll be able to complete your tax return on the back of a postcard!” they say with a wink. 

“We’re going to make filing so easy we’ll put tax lawyers in the unemployment line!” they say, laughing.

And I laugh and laugh.

Because when they’re voted into power, Republicans do little to nothing to simplify the ever-more-complicated tax code that causes the self-employed to worry about heart attacks, which I can afford even less because my 2021 premium jumped again and I had to switch to an even higher-deductible plan. 

Now the Democrats control the White House, the House and the Senate. They promise to tax only the rich and leave the rest of us alone. 

And I laugh and laugh - as I brace for new tax complexities that will cause me even more grief.   

I’d love to go skiing on gorgeous snow-covered hills and forget about the tax agitations that are already dragging me down.

But I’m afraid to spend the money to go skiing - because, like every year, my tax bill is going to be way higher than I thought it would be.  

Gosh, I hate this time of the year. 

Tom Purcell is a Pittsburgh Tribune-Review humor columnist. Send comments to Tom at Tom@TomPurcell.com.