Tax Time Migraine

The finish line is in sight

When I was a kid, it was a visit to the dentist that left me paralyzed with anxiety for weeks before the fatal day I had to sit in the sadist’s chair. A childhood full of much more candy than toothpaste, I was almost guaranteed to get drilled. But now that I’ve grown up, visits to the dentist are a relief. I know he’ll end the pain (even if there’s some involved to reach the finish line) — and I almost look forward to the moment.

But not to worry, because tax season has replaced the dentist in my adulthood. I shudder at the thought of computing my taxes for months before finally sitting down to perform the odious task.

Had I followed my instincts and simply bought a 5 year CD the day the fed returned my portion of my seized assets, tax time would have been relatively simple. Interest income from just one banking institution is about as easy as it gets.

But no. I had to follow my brother’s advice and hire his broker to manage my money. Not only do I now suffer the ups and downs of equity markets — but my tax computations involve all sorts of terms I still don’t — and don’t want — to understand.

OID’s, dividends, tax-free income, foreign income, qualified dividends, unqualified dividends, ordinary dividends, capital gains (of which I have none), capital losses (of which I have enough to write off until I’m 106 years old). I mean — who gives a shit about all this crap? Not me. That’s for sure.

When I went to prison, I had no choice but to hand over my tax deal to my brother. It’s virtually impossible to file income tax from prison. I guess they figure prisoners don’t make any money, so why allow for the contingency? I know. They forgot about guys like me. My sibling’s guru charged $500 and made a couple of stupid and sloppy mistakes. I fired him. I don’t need no stinkin’ human stupidity. So I went for the artificial stuff: Turbotax. Much better.

This year held special nightmares and headaches. I had all sorts of 1099 hustles (here and DoorDash), plus social security, some freelance writing, and the worst, unemployment insurance — which is taxable this year. I knew it was going to be a slaughter. My estimated payments weren’t going to be near equal to what I owed.

Yesterday, I sat down to do the job. Fortunately, Turbotax actually imports all the complicated stuff from most leading brokerage accounts. You don’t really have to know what all those terms actually mean. But still, there are clicks, bangs, and glitches along the way. Too many forms — too little time.

I spent 6 hours at it yesterday. And then another 2 today. Finally, another hour on the phone with Turbotax asking why they charged me for personal help that I didn’t use. (That’s the second straight year they did that. Apparently, Turbotax has a bad habit of overcharging people.)

But I gotta tell ya. It’s an impressive program. When my situation was simpler, I could file with free software. But not now. Just too complicated. Still, for $157, I feel I got a bargain. Admittedly, a minor victory after losing 5 figures in the stock market yesterday.

Speaking of the volatile equity markets — what I wanna know is why doesn’t somebody just kill Putin (the major cause of my paper losses)? Clearly, he’s the 21st century’s Hitler and Stalin all rolled into one. But that’s a story for another day.

If you’re stressing tax day — and your accountant’s a loser? Try Turbotax. It’s March 8th and I can already see the finish line — which I’m approaching that much faster as I’m so much lighter in the pocket now. Did I mention I’m drinking beer without a care in the world as I tap this out? Yeah, Turbotax. Rock on with your bad self.