Wait, I Still Have to File Taxes This Year?

Denver, CO 2/13/2025

BUSINESS OWNER’S PANIC ROOM—In a tragic but predictable turn of events, local entrepreneur and Dames member, Alice Whitmore, awoke in a cold sweat at 3:47 AM, struck by the horrifying realization that, once again, she had to file taxes this year.

“You mean it’s not just a one-time thing? I have to do this every year?” Whitmore muttered, eyes dotting back and forth, frantically scrolling through her inbox, ignoring the 74 increasingly desperate emails from her CPA labeled ‘URGENT: Please send receipts TODAY.’

After somehow blocking out the fact that tax day is, in fact, the exact same day every single year, business owners across the nation are yet again blindsided by the IRS’s audacious demand for their “fair share.”

“I don’t get it,” said fellow Dames member and marketing consultant, Rachel Montgomery, shaking her head. “I filed last year. I paid my dues. Why do they keep coming back like a clingy ex who just won’t take the hint?”

Indeed, millions of business owners are reporting similar symptoms of tax-induced amnesia, despite the fact that April 15th has been a national day of financial reckoning since, well, forever.

Meanwhile, tax professionals have reportedly been bracing for the annual tsunami of small business owners who swore they would ‘stay on top of it this year’ but, in reality, are now attempting to piece together 12 months of transactions from a shoebox full of crumpled receipts and cryptic Venmo notes labeled ‘????????’.

“I had a system,” Whitmore insisted, flipping through a suspiciously empty spreadsheet titled ‘2023 Deductions’. “It was color-coded and everything. I just… never actually filled it out.”

Despite their best efforts, small business owners across the country continue to be shocked that tax day arrives with the same relentless consistency as Mondays and pumpkin spice lattes in September.

“I mean, how is it already April?” Montgomery lamented, enjoying a gummy at a ‘stress relief’ brunch that conveniently doubled as a networking event where absolutely no one had time to discuss their actual taxes. “It was just January, like, two minutes ago. What is this sorcery?”

Meanwhile, CPAs everywhere are reportedly entering their annual fugue state, fueled solely by caffeine, pure chaos, and the desperate hope that this might be the year their clients finally get their act together.

Sources say that’s highly unlikely.

“It’s the same song and dance every year,” said tax preparer Linda Hawkins, who has been ghosted by 16 clients this week alone. “They swear they’re on top of it. Then, two days before the deadline, I get a panicked email asking if ‘buying a $3,000 personal laser hair removal system as an investment in self-care’ can be deducted as a business expense. I’ve stopped trying to reason with them.”

At press time, Whitmore was seen frantically Googling “tax extensions” and “how to deduct a jet ski” as a legitimate business expense.

Look, taxes are inevitable—but at least you don’t have to suffer alone.

When you’re part of The Dames, you’ll never be the only one panicking at 3 AM, questioning whether your impulse purchase of a “business inspiration retreat” in the Maldives is deductible. Because let’s be honest—we’re all in this together, and someone in your Think Tank Circle definitely is or has a great CPA (or at least a good laugh about why last year’s jet ski was a “marketing expense”).

So, take a deep breath. Pour another cuppa. And rest easy knowing that in The Dames, we’ve got your back—whether navigating tax season, scaling your business, figuring out how you’ll possibly get to daycare to pick up your kids on time today, or just making sure you don’t commit financial fraud in the name of “self-care.”

Want in on the fun? Apply to join The Dames today.?

We promise—no judgment, just solutions (and maybe a little tax-time commiseration).