This past night I worked on my taxes, a stressful endeavor. I am an independent contractor, which has made things way more complicated than they used to be. I’ve been using the Free File program to use online applications for filling out taxes for years now, usually using TurboTax or H & R Block. They abstract from the forms and walk me through everything, and often provide help when I’m confused, but they can sometimes be worded confusingly. I just do the best I can. The biggest problem with the abstraction is that everything is trapped in this interface, so it’s hard to review it yourself and make sure everything is right.
Every year I worry that I’ve done something wrong, and this year is no exception. Since becoming an independent contractor, having to pay estimated taxes, I don’t really get a “return”, either applying my over-payments to next year or often having to pay additional. This year, though, I have a rather large over-payment, more than enough to pay my first quarterly estimates for 2016. That worries me. I’ve made a fair amount less than last year, so it may be right, but I’m still unsure. I’m going to sit on it and come back to it another night, see what I can do to review it.
Another thing I do every year is say that next year I’m going to work with an accountant. Every next year I wait until it’s too near tax time to comfortably figure out how to do that. I don’t really know how that works or what it would cost. It’s more of a consultation and review of how I’m doing the taxes myself that I need. Maybe next year. We’ll see.