Every single year without exception, tax time stresses me out. It’s something I struggle through from the moment I start thinking about taxes — usually somewhere in mid-December, because the year’s ending and oh boy I should start putting together that expenses list again — to the moment everything is filed and I’ve put the checks in the mail. (Yes, I pay the majority of things online; for some reason, though, I always pay Portland’s Arts Tax with a check. It’s the one thing I use my checks for, still. That’s not a joke; literally the last time I used my checkbook was this time last year, to write a check for Arts Tax.)
The stress surrounding taxes comes in waves, in different flavors. Gathering together all the information I need in the first place, and stressing simultaneously about how little money I made in any year and how much of it I spent on things that are literally unavoidable, like rent and groceries. (Honestly, my discretionary spending is shockingly low; I just can’t afford it.) Wondering if I’ve missed some expense, some information that would change all the math. Checking where all my 10-99 forms have gone. (One year, I’ll remember to store them all in one place as they arrive, I promise.)
And then there’s the anxious wait for my CPA to tell me how bad things are, and the feeling of, welp, I guess I didn’t want to save any money after all when I actually get the information back. I didn’t use an accountant for many years, and then the first year that I did, he told me that I’d been missing out on a lot of possible benefits I could have claimed, but also that I’d been failing to pay a freelance tax for years; after that, having a tax guy became a must.
I’ve mailed everything off for the year as I write. But even now, the stress isn’t entirely over: what if this is the year I get audited? What if there’s a mistake in there I didn’t catch? Surely there’s some way I could do this better? Maybe a month from now, I’ll be able to think of something else again.