Thursday, February 24, 2011

There comes a moment, 20 minutes into TurboTax, when all the world turns still and quiet as your cursor hangs above the “Continue” button. You’ve taken your lumps after plugging in your income statements and now, with the deductions section before you, your chance for redemption is at hand. Here is your opportunity to turn it all around, to take that ticker in the upper-right of your screen and transform it, through the alchemy of tax law, from red to green. That’s been the ritual for the last two or three filings, at least, and it’s worked well for me.

But it didn’t work this year, and try as I might that number stayed red. Very, very red. On one hand, there was a perverse sense of gratification here, because this was a milestone. Through hook or by crook, I was in a completely different bracket. This was big people territory now, with RSUs and stock options and– And a sizable chunk owed to state and country, which brought me straight back to earth. I was annoyed. I mean, a third of my paycheck disappears into the ether every two weeks, and once you pile on property and automobile taxes, well, that civic duty checkbox feels sufficiently checked.

It was, like, what am I paying for now? I had just read a piece on state pensions, and the thought of funding those, however misguided, was cause for anger. A pension! In trying to ascertain precisely how the fuck a pension even works, I may as well have been ruminating over other fantastical conceits, such as a unicorn strapped to a jetpack or diet fries. I quickly clamped down on this train of thought, however, because it wasn’t productive at all. There were taxes to be reported. This was the challenge at hand.

And what a challenge it’s proven to be. I’ve yet to file. I’m stumped. I suspect the mathematics needed to unravel this beast really only call for addition and subtraction, but where in fresh hell those pluses and minuses go eludes me. I considered going to H&R Block, until I discovered this thread, where tax professionals were asking questions disconcertingly similar to mine. I saw it instantly, the full experience run-rated across my mind’s eye: stepping into a green and off-white office, pulling up to a desk made of simulated wood, and then watching someone fumble through my paperwork or, even worse, feigning competence while royally screwing the pooch. So what’s the fix? Research, plain and simple, by canvassing financially savvy peers for insight. I’m dowsing for answers, and I think I may have found them.