Behold the mighty ping-pong table of misery:

Uncle Sam is ruining my ping-pong skills

Those are my tax documents, semi-organized by type: W-2s in one pile, charitable contributions in another… three piles for 1099s – the MISC ones from my wife’s side hustle and my side hustle, plus DIVs and INTs. Receipts, tax bills and business expenses, oh my!

Each year around this time, I retreat to my subterranean lair to work on our tax returns… and invent new curse words (most are portmanteaus of other curse words). Just me and my good friend TurboTax Deluxe.

Other folks have suggested that I outsource this pain-in-the-butt job. I know quite a few folks who claim they have a mythical tax prepararing wizard who does yeoman’s work for a mere pittance. “I just give [him/her] a shoebox stuffed with documents… and [he/she] only charges me $100!”

But I’ve made a several calls and the price I’m quoted is significantly higher than a single Franklin. Also, my bookkeeping system is only slightly less disorganized than a pee-wee soccer game… I’d probably have to spend more time explaining it than I would just going the DIY route.

It’s the side hustle gigs that really add 27 extra layers of complexity (and when we’re talking about IRS forms, that’s really saying something!). My wife teaches fitness classes, and I do some freelance writing. (Can you believe someone actually pays me for my words? I can’t either! But let’s just keep it our little secret.) For the paltry amounts we both earn in these gigs, we have to fill out dozens more IRS forms. Oh what fun it is to fill out a Schedule C!


Now that three of my kids are working part-time jobs, I file returns for them as well, or at least crunch the numbers to see if they’d get a refund. Oh goody goody… more forms!

So if you don’t see me out and about for the next few weeks, you’ll know why. And if you do see me and I’m miserable, you’ll also know why.