Tax Day is A-Comin’
Math, Mayhem, and the Madness of April 15th
It’s the top of April, which means Uncle Sam has his hand outstretched, palm up, and he’s waiting for his cut. Yup, it’s time to do those taxes. My taxes have gotten a tad complicated lately. I have an LLC for my freelance work, which provides protection and asset separation, but it also means my taxes are due earlier. Thankfully, I’m already through the process.
But if you’re like me, it doesn’t matter when the tax deadline is. You’re waiting until the last possible moment to prepare.
While I’m very buttoned up with my family’s fiances, my flow for approaching the business books is more like: I swipe the business credit card, the expenses flow into Quickbooks, and there they sit. I do not touch them. I do not categorize them. I do not even glance at them. Somewhere in that app's depths, I swear I can hear muffled cries begging me to reconcile my expenses.
I, of course, do not.
Instead, I text my friend Dave. He and I share a special talent for moving “get ready for taxes” to next week’s to-do list. Every. Single. Week. We’re also both math nerds, which means we text each other updates with the enthusiasm of curlers on a fresh patch of ice.
“OMG, I figured out why the balance sheet was off! Double-coded a PayPal transaction as gifts. Woo!”
I attempt to share these victories with my wife, Mary. She does not care. Her eyes glaze over. She stares through me. I know she hears me, but she does not respond. And I’m sure that deep in her soul, she thinks less of me each time I burst into the kitchen shouting, "Baby! Get this—my net income looked off because I accidentally depreciated the office chair I bought last year over five years instead of three. I was out here trying to extend the lifespan of a $99 IKEA chair like it was a Macbook Pro."
Who can blame her? I fell asleep while typing that sentence.
I do love solving these financial mysteries. I just don’t like doing the work.
Cut to December. The “Reconcile expenses in QuickBooks” task had been punted to “next week” for six months straight. But tax time crept closer, so I escalated it to my “Things to complete over the break” list. The situation was serious.
Then the break came, and two things happened: my main freelance gig was put on hold, and my doctor told me I had the celiac. So, did I deal with my expenses? No. I gave myself the gift of not doing them.
But the tax appointment loomed, so the first two weekends of January, I hunkered down. Eight hours of categorizing expenses. I was a woman on a mission, in a sweatsuit, with a sweatband, shouting, “LEAVE ME ALONE! I AM DOING THE BOOKS!” at anyone who even dared to walk by my desk area.
Then, I moved on to tax prep. Another eight hours.
All done. Ready for taxes, and once again, I whispered to myself, “I swear to gawwwwd, I will never do this again.”
I don’t understand this side of myself. I’m an organized AF person. I mean, for the love of all that is holy, I have multi-tiered to-do lists ranked by urgency. Yet, I cannot bring myself to categorize a simple business expense in real time.
This is not new behavior. Back in the day, when I was an executive assistant, I despised completing my boss’s expense reports. I avoided them at all costs. Eventually, when things started getting out of hand, I went in on a weekend, blasted music at my desk, and powered through the disaster I created. It would take all day.
It got so bad that at one point, my boss Tom’s Amex bill hit $35,000, and he sheepishly walked over to my desk and said, “I think you have an unrealistic view of how much money I make.” I spent another entire Sunday fixing it (and put in for the overtime - what the corporate overlords didn’t know wouldn’t hurt them).
Now that I work for myself, apparently Quickbooks is the new Tom’s expense reports.
This year, I’m aiming for quarterly check-ins. Maybe—just maybe—if the process isn’t so hideous, I’ll be more inclined to get this shiznit done.
At this point, it’s too soon to tell which Robin will show up: To-Do List Powerhouse Robin or I’d Rather Die Robin.
So, if you’re out there procrastinating on your taxes, let me give you that gentle kick in the pants to get going. Also, please know you’re not alone. I feel your pain. I see you (and that pile of receipts in the blue folder on your desk).
And hey, if we’re looking on the bright side of things, Uncle Sam will be the only person left working on our tax returns after Elon finishes decimating the government. That has to improve the odds when it comes to an audit.
If taxes have your brain in a knot, just wait until you hear us try to untangle the basics of personal finance. This week on my podcast Well…Adjusting, we’re talking money—401ks, mutual funds, high-yield savings, and why Steph, our very Canadian producer, is completely baffled by the American financial system. I’m no expert, but I do love a good money chat, so we’re breaking down the essentials in a way that won’t make your eyes glaze over. If you’ve ever wondered how to build wealth, avoid credit card chaos, or just stop feeling like you’re always behind financially, this one’s for you. Take a listen wherever you get your podcasts or click below!