A taxing time

I’ve put it off long enough: As soon as I finish writing this, I’m starting my taxes. If I don’t wrap it up today, it’ll be a weekend project. Oh, joy.

While I’ve noted before that I tend to procrastinate tasks I’m not thrilled about, waiting this long doesn’t fall into that category. True, I dread doing the taxes, but the real reason for my delay is simply that I had too many other fish, each of which needed frying. But at this point I can wait no longer.

After seven years of being self-employed I’m still getting the hang of it, but it’s not like I’m heading into the task unprepared – I categorize absolutely everything throughout the year, and have numerous envelopes of receipts, check stubs, 1099s, etc. to calculate deductions, all of them organized and with copious notes. I think I’m single-handedly keeping the Post-It Notes people in business. It takes only a few seconds to do that each time I save something, but it saves hours of work every April.

In spite of that, I’m terrified I’ll claim something inappropriate, and for that reason I always underestimate a bit and/or err on the low side – if I do it wrong, I don’t want to over claim anything. If I look at a receipt and have a doubt, I toss it out. I used to know an economics professor who would be at a loss to understand why I refuse to claim every single item, no matter how small, and in fact used to encourage me to do exactly that. But as far as this self-employed thing goes, I prefer to go slowly. A bit wishy-washy of me maybe, but I don’t want any surprises a few months from now.

That said, even though I play it as safely as possible, each year I figure my taxes a bit more aggressively than the previous year. That feels good as long as the results aren’t too shocking after finishing up that tax form. And except for my first year on self-employment – a total monetary disaster tax-wise – I’ve been doing pretty well with it.

I’ll let you know next week how it went.

A.J.