Scary Bookkeeping Stories – The Drawer



Only Candace and her administrative assistant Daphne knew what was in The Drawer.

Candace had an open-door policy in her business. Not only was her door always open to her employees, but she often let them use her office as a quiet workspace while she was out meeting with her customers. She only had one requirement: the drawer on the top, left hand side of her desk was not to be opened, under any circumstances.

Rumors abounded about what was in The Drawer. Some of the rumors would have sent HR into a frenzy. But Candace’s employees respected her, and The Drawer remained a workplace mystery.

And then, the letter arrived from the IRS.

Usually, Daphne opened all of Candace’s mail, sorted it by priority, and left it in her inbox. But the day the letter arrived, Daphne handed it directly to Candace, a worried expression on her face.

Candace read the letter. Then she read it again. She looked over the top of her glasses at Daphne and quietly said, “Close the door.”

Employees, upon seeing the door closed for the first time anyone could remember, began to speculate. Some of the speculation would have sent HR into a frenzy. The employees whose desks were closest to Candace’s office took off their headsets and strained to listen to what was happening in the office, while trying to appear as though they were not eavesdropping.

Inside the office, Daphne asked, “What are you going to do?”

Candace glanced down at the letter. “The audit covers our first year of business, which was almost three years ago. I guess it’s time to catch up.”

Candace hesitantly reached out her left hand, pausing as it settled on the handle of The Drawer. Daphne gulped, and Candace took a deep breath.

Slowly, she eased open The Drawer.

The explosion of receipts and invoices wasn’t audible outside of the office, but Daphne’s gasp of horror was. Moments later, she emerged from the office, arms full of faded and crumpled bits of paper. Trying not to succumb to tears, she returned to her desk and started trying to sort the documents by date.

Meanwhile, in her office, Candace gazed forlornly at The Drawer, now empty except for one item on the bottom:


While this story is a work of fiction, the existence of a “bookkeeping system” that consists only of a drawer full of receipts is all too real for many business owners. I never understood how anyone could run a business this way until a client confessed to operating his business based on his bank account balance and filing his tax return using information from his bank statements.  

I shudder to think of the tax deductions he missed.

Bookkeeping doesn’t have to be scary. Even if you don’t think you are at a point where you can hire a bookkeeper on an ongoing basis, hire one to help you set up a simple system using a cloud-based accounting program like QuickBooks Online (link) and commit to updating it at least weekly. No data entry means you can finish your bookkeeping quickly, as long as you don’t let it pile up on you.

Trust me, you and your administrative assistant would much rather have nightmares about psycho killer clowns than to actually live out Daphne’s and Candace’s nightmare.

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