Simpler Taxes Long Promised, Never Delivered

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.

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