What’s Your Tax Strat?

It’s (almost) the most wonderful time of the year.

Call me crazy or call me extremely organized as a means of working against my tendency to procrastinate, but every January near the end of the month, I watch the mail like a hawk, waiting for my tax documents to come so that I can do my taxes and get it over with.

When I had a full time job, I was always the first to email HR about the W2s, eager to sit down in front of TurboTax with a notebook and a freshly-sharpened but entirely unnecessary pencil and do my taxes. Horror stories from friends and family members who avoided their taxes for years only to have the IRS catch up with them eventually instilled a healthy sense of fear in me. Doing my taxes early gestured at a limp sense of responsibility — my own personal way of proving to myself that I’m on top of it, that I’m with it, that I have this whole thing on lock.

In those halcyon days before freelancing, my taxes were dead simple. There was one form, the numbers of which neatly corresponded with the boxes I needed to fill out in TurboTax. If ever I felt lost or panicky, there were signposts and guides throughout, dumbing down the already-simple process and breaking down any intimidating language via a series of gentle exhortations, assuring me that hey, it’s okay, we’re going to get through this together.

There are few things as satisfying as inputting numbers in a box, clicking over to the next screen and watching the money that will soon zip your way via direct deposit grow in size. The payoff for performing one irritating personal administrative task that takes less than two hours to complete is well worth it. Putting this task aside, shoving it to the bottom of an ever-growing and mutating to-do list felt like delaying the inevitable. We all have to pay taxes; might as well do it early, get the money you’re owed and move on with your day.

Freelance taxes are an entirely different beast; I alternate between terror and elation when I think about doing my taxes this year, even though I know and hope that I have the money saved to pay them. It will be much less fun. I will have to talk to an accountant. I will spend a fretful Sunday poring through my bank statements and highlighting things I think I can deduct. I’ve only been freelancing for six steady months; the first half of this year I worked full time with a job that took my taxes out. I’m hoping this saves me in the end.

Still, I watch the mail with growing impatience, checking each 1099 as I get it off my list. Part of this fun is seeing just how much money I made this year, but it’s tempered with my frantic arithmetic, calculations performed on my phone, looking at the money I made and ballpark-ing what I’ll have to pay. Once I’ve gathered all the papers from far and wide, I will go to my accountant and lay it all out on the line.

No one else I know is like this; I know very few people who look forward to paying their taxes and do so early and with vigor. Have you planned? Are you ready? Do you break down the door of HR, clamoring for your W2s as soon as you’re able? Will you wait until the absolute end and do your taxes in a panic, covered in a thin sheen of night sweat?

Tell me. Please! I want to know.

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