It’s this time of year when I yearn for the good old days, when I worked a regular, full time job. I don’t miss the hour plus commuting to the Cities, where I would listen to heavy metal to circumvent my potential road rage. I don’t miss the Dilbert meets Office Space mentality of corporate America, where the focus is more on the ass (kissing and covering) and less on the head (that’s where the brain is. Lord forbid, we acknowledge it).

What I do miss is the EZ40 tax return. When you work full time for a big outfit, they have this groovy withholding mechanism in the accounting department called FICA. Basically what it does is forward the government waaay more of your money than they rightly deserve to spend however they want all year long. Then when the new year starts, and you get your cute little W2 form, you get to file what is basically a grievance to get your damn money back, and the government acts like they are giving you a gift. I miss that brainwashing.

People who work in this delusional dynamic happily go to their accountant (if they own property or have kids, because itemized W40s can get complicated), confident that they have a sizable check going into their account a month from that time. Entire industries are built around those people. Need a loan from the bank? Just bring in your W2’s. Want to get a car? Same thing. I used this handy option when I worked full time and the furnace died in my house on Thanksgiving (calamities always seem to befall me on holidays. More on that later).

When you belong to that cursed scorge on society called “Self Employed”, nothing is EZ, especially taxes. W2 People get their income taxes filed as soon as possible, usually February (conveniently corresponding to all of the President Day sales, oddly enough). 1099 People wait until the last possible minute to prepare and file those wretched forms; March, if they are organized, April if they are not. Because 1099 people don’t give the government money ahead of time, they typically don’t get squat back. There’s nothing to look forward to.

Since I have waxed poetic on numerous occasions about my propensity to put things off, it’s no great surprise that this year, taxes were prepared from 9:30am to 5:00pm for our tax appointment with Steve-the-tax-guy at 6:15pm.

Self Employed people have to keep track of everything. Everyone who works is familiar with the terms, Gross income (it’s not covered in slime, it just means massive; not a great term, but it’s what used) and Net income (like a fishing net with lots of holes; you get to keep whatever doesn’t fall out). For W2 people it’s simply two numbers on the form. For 1099 people it consists of insurmountable calculations involving multiple tax forms called Schedules (which I can only equate to the sheer amount of time it takes to fill them out).

On the outset, it looks like self-employed people get away with crap, because you can write so much off. They don’t. The IRS loves to audit self-employed people for the same reason anyone who loans money hates self -employed people. They are not the norm, and they are always picked on. For this reason, meticulous records and receipts must be maintained and presented as proof that what you are writing off is legit. It’s like being self-employed automatically makes you guilty of something, and you have to present evidence to the government so they don’t throw you in jail; like being self-employed is akin to being on parole.

So, we have roughly two weeks to cough up money that most people get screwed out of all year. Except, we only have to bend over once, and we’re not ironically happy about it. In the end, I guess it all evens out.

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