5 Things That Make Bookkeepers Cry (And 2 That Make Us Cheer)
- Simon Zryd
- Aug 18
- 2 min read
If you think bookkeepers cry over math problems, you’d be wrong.
We cry over messy records, mystery transactions, and enough crumpled receipts to wallpaper the Denver Public Library. But we also cheer—loudly—when a client hands us a clean, reconciled account.

Whether you’re a Denver small business owner just hiring a bookkeeper for the first time, or you’ve been flying solo with QuickBooks until now, here’s the inside scoop on what makes us reach for the tissues (and what makes us do a happy dance).
The 5 Things That Make Bookkeepers Cry
1. The Shoe Box of Doom
You know the one—it’s a cardboard box filled with random receipts, unopened bank statements, and possibly a rogue granola bar from 2019. We love documentation, but we prefer it organized. Dumping a year’s worth of paperwork on your bookkeeper is basically the financial equivalent of a horror movie jump scare.
2. Mystery Transactions
“Oh, that $3,276 charge? I’m sure it’s fine.”Mystery transactions make us twitch. Without receipts, notes, or at least a vague recollection of what the charge was for, we’re left guessing—and the IRS does not appreciate guesswork.
3. Late Bank Reconciliations
Bank reconciliations aren’t just busywork—they’re your business’s early warning system for fraud or errors. When they’re months behind, little mistakes turn into big headaches.
4. The “I’ll Do It Later” Approach
When you push off updating your books, you’re basically planting a financial time bomb. Tax season becomes a scramble, and your financial reports will be about as useful as a weather forecast from last year.
5. Mixing Business and Personal Expenses
Your business checking account is not your personal piggy bank. Mixing funds not only makes bookkeeping harder, but it can cause serious tax and legal issues. (Also, we can tell. Every time. No exceptions.)
The 2 Things That Make Us Cheer
1. Clean, Organized Records
When a client hands over categorized expenses, reconciled statements, and clear notes on each transaction, we light up like Union Station during the holidays. It means we can spend more time giving you insight and less time playing financial detective.
2. Clients Who Ask Questions
Bookkeeping isn’t just data entry—it’s a partnership. When clients ask questions about cash flow, profit margins, or tax strategy, it shows they’re invested in understanding their business. And honestly? That’s when we do our best work.
Bottom line: Your Denver bookkeeper (hi, that’s us at Clearbookz 👋) wants you to succeed. A little organization and communication can turn bookkeeping from a tearful task into a high-five-worthy collaboration.
If you’re ready for fewer tears and more cheers in your business finances, let’s talk. We’re the affordable bookkeeper in Denver who actually enjoys this stuff—so you don’t have to.
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