Drowning in paper, death by papercut

April 14, 2008 by Tim

So I filed my taxes last night.

Tax returns are pretty much a thing of the past for me. When you’re self-employed, you have to send the government a check four times a year based on what you think your taxes will be. Frankly I always lowball it. I figure as long as I’m sending enough money to avoid an “underpayment” penalty come tax-time, I’d rather have the money in my bank accounts throughout the year, than wait for a lump-sum return check and pretend like it wasn’t my money to begin with.

So come tax season I always owe money, which is fine, but so there isn’t a lot of incentive to get them hammered out in January anymore. Plus with everything that seems to fall at the beginning of my year (Winter-een-mas, new books, Digital Overload), free time seems to conspire against me. But I think this is the closest I’ve ever cut it to the filing date.

Taxes don’t bother me as a whole. What bothers me about tax season is that is serves as an annual reminder of my inability to maintain any semblance of organization for my paperwork. Despite my best efforts to get organized after taxes, twelve months later, I’m rummaging through dozens of drawers and boxes and closets to collect all the receipts, check stubs, bills, etc.

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