Letters to the Tax Man
Being self-employed, I owe the IRS money every year. It’s one of the very few downsides to not having to deal with an incompetent boss on a daily basis.
But like the old saying goes, “Nothing in life is certain but me blowing my nose in the shower and using the same knife for the jelly as I do for the peanut butter, even though my wife has asked me countless times not to do either. Oh, and morning boners and taxes, too. Those are also fairly certain.”
After the initial shock of seeing how much I owe each year wears off, I’m typically okay with the giant check (or, 99.9% of the time, several small checks) I have to write, because as the greatest movie ever made starring marionettes put it:
Freedom isn’t free,
It costs folks like you and me,
And if we don’t all chip in,
We’ll never pay that bill.
Freedom isn’t free,
No, there’s a hefty fuckin’ fee.
And if you don’t throw in your buck ‘o five,
Who will?
Pure poetry, isn’t it? Well, for more than 1.4 million people this year, probably not. That’s because according to a report on CNN.com, that’s how many people were audited last year and even more audits are expected this year.
I'll bill you for your letter once I know how much I owe the government.
Not good. What if you’re one of the unlucky millions audited this year and it turns out you made one tiny mistake on your taxes and you now owe the government some scratch? Well, I might be math and financial common sense-challenged, but I think I can help. After all, I did spend two weeks right out of college working for American Express Financial Advisors.
While I’ve never been audited, I am an expert in owing Uncle Sam money and thus, I’ve become quite good at writing letters requesting to be put on a payment plan. Because, let’s be honest, who actually plans ahead to be able to pay the taxes they owe all at once? (Smart people and people who don’t have mountains of credit card debt, that’s who.)
Typically, the process goes like this: you owe taxes that you can’t pay in full. No problem. Just file your taxes and include a letter stating your need to go on a payment plan. They’ll send you the forms and viola! You can sit back, relax and comfortably pay the government your unpaid taxes (plus penalty and interest) over the course of the next year, where you’ll likely write your last check just in time for the 2010 tax season!
Or…and I’m just spit-balling here, you could pay me to write a letter so pathetic and so riddled with spelling and grammatical errors for you, that the agent assigned to your account can’t help but feel sorry for you, and subsequently wipes away all the unpaid taxes you owe in a Haley Joel Osment fit of paying it forward.
Will it work? Probably not! Is it a risky and foolish way to spend your money? A million times yes!! Will I guarantee results or provide a refund of any kind? Hell no! Will the letter be put up on a bulletin board and ridiculed relentlessly before leading to a hearty and spirited discussion about the state of the education system in the United States? Sure! But isn’t that the exciting thing about being on the ground floor of something?
Now, the painstaking amount of time I put into writing your letter using my proprietary method doesn’t come cheap. I’ll take a look at each person’s situation and charge on a case-by-case basis. But in general, you can expect a bill after I frantically file my taxes the night of April 15 and find out how much I owe.
So what do you say, Internet? What’s it going to take to get you in an IRS payment plan letter written left-handed with magic marker and so riddled with spelling and grammatical errors that the agent reviewing your account vomits with pity and wipes away all your debt?
