Maybe I Can Do My Own Taxes

Probably not. But maybe?

After talking with a friend the other day, I became convinced of the fact that I could possibly do my own taxes.

My friend freelances full time and has been doing his own taxes for the entirety of his freelance career. He’s distrustful of accountants. “What if they’re doing something funny with my money?” he told me. “Why would I trust them?”

I am untrusting about the petty things and trusting to fault about larger, more life-threatening things like the fact that my landlord certainly won’t kick us out of our apartment and raise the rent to its market value anytime soon. On an individual level, I trust no one. Even though institutions have done nothing to prove to me that I should have their trust, I still place it blindly and with gusto in their hands.

I know that I need to pay my taxes so that the IRS doesn’t beat down the door of my apartment. I know that I am bad at math and easily frustrated with things that seem like they should be easy but in actuality are not. This is why I have an accountant. This is why I dutifully print out my bank statements, highlight all the things that aren’t food, rent or cigarettes and press that stack of paper into my accountant’s hands. I can’t be trusted to deduct things! I honestly don’t know what I’m doing!

When my friend heard that I already half the work, he asked me, “Why don’t you just do them yourself?”

Here’s A Surefire Tax Estimating Process for Freelancers (Rebooted and Updated)

One night, it seemed possible that I could. Somehow, I have received all the pieces of paper I need to do my taxes and it’s only February. I’m dragging my feet to make the appointment only because I want to make sure that I have everything — I kept terrible records last year and I’m sure there’s something that slipped through the cracks. My own personal calculations made me realize that I have absolutely no idea what I’m doing.

Then I found a tax table for 2016. I looked at the numbers I’ve scratched down in the back of my planner. I added them up. I remembered that for half the year, I had been a salaried employee, with taxes already deducted. I did some more math. I smoked a cigarette, ate a Kit-Kat and realized that I’m not going to owe nearly as much as I thought I would. My taxes, impenetrable and labyrinthine as they might be, could be something I could do myself.

I haven’t decided if I will yet. The challenge is appealing — to tackle the monster that is my taxes and come out victorious on the other side — but my fear of fucking it up kicks in, every time. I’ll think on it. I’ll ask my dad. And then, I’ll probably call my accountant.

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