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Attacking taxes

This year’s tax returns for all of us are going to be … interesting.

Thanks to my friend Mr. TurboTax, I’ve gotten very good and fast at the yearly chore of filling our income taxes. Working for myself since 2006, I’ve not only gotten plenty of practice on taxes, I’ve learned how much of one thing or another I need to do, and how little of something else I need to do or not do. Estimated taxes? Got it down to a science.

But, 2020 was not a normal year. (I’m guessing you may have noticed.) While I didn’t change what I did, I had the good fortune of doing a lot more of it last year with more assignments than usual. That’s fantastic, of course, but it also means I may have underpaid those estimated taxes. That’s not an issue penalty-wise, but it will certainly change what I owe this year.


Meanwhile, my wife is a substitute teacher, which, in 2020, is an occupation that got the new moniker of “gig worker” for employment purposes. That means she was eligible to collect unemployment, which was a real lifesaver for us. This was all new during the 2020 spring semester, so we didn’t do withholding. At the beginning of the 2020 fall semester, we did. So, part of what she got was covered, part wasn’t. As to how all this figures into actually doing the returns, I have no idea. (Although I’ll find out right shortly – I’m starting our taxes right after I finish writing this.)

Bottom line is that everybody’s tax returns have a lot of monkey wrenches tossed into the mix, and I doubt the procedure will bear much resemblance to previous years. Add in the effects of withholding and not withholding, unemployment taxes, additional 1099s – both mine and hers—and half a dozen other things, and I think I’m in for an interesting afternoon.

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