Taxes really tend to hurt quite a bit more when they’re not being taken out of your paycheck automatically by the company you work for. Since the company I work for is my own, and I don’t have it setup to take taxes out automatically, I have to take them out myself.

Unfortunately for myself, I haven’t been very good over the past year putting putting money aside like I should. I now have the honor and joy of writing the IRS a $16,000 check. This is just a rough guess of what I’ll need to pay considering I filed for an extension, but nonetheless, I’d consider it a pretty accurate guess. Starting this year, I’m going to start doing quarterly payments(even though I should have started doing this a long time ago). Unluckily for me, the first quarterly payment was due at the same time as the payment for last year’s taxes.

Cutting two substantial checks to give away at the same time is not fun, not fun at all.