Common Bookkeeping Mistakes. Confessions of a Bookkeeper: 5 Hilarious Habits That Are Destroying Your Books

Let me start by saying: I love my clients.They’re passionate, driven, full of big ideas… and sometimes completely, irreversibly allergic to receipts. As a bookkeeper with over 25 years of experience (and enough coffee in my bloodstream to rival a Starbucks), I’ve seen things. And today, I’m begging—literally begging—you to stop doing these common bookkeeping mistakes.

1. Mixing Business and Personal Like a Margarita Common bookkeeping mistakes

If I had a dollar for every time someone swiped their business debit card at Sephora, I’d be semi-retired and sipping something fruity.

Why it’s a problem: It makes your books messy, your tax filing stressful, and your deductions questionable.

Fix it: Open a business bank account. Use it for business only. Step away from the Prime Day deals.

2. Dropping Off a Shoebox Like It’s 1997

Look, I appreciate a good throwback. But if you hand me a shoebox full of receipts and say, “Good luck,” don’t expect me not to cry.

Why it’s a problem: Faded, crumpled receipts = missing deductions and a whole lot of guesswork.

Fix it: Snap photos with your phone. Use apps like QuickBooks or Dext. Or just… folders. Literally anything organized.

3. Saying “I Just Need a Quick Cleanup” (When You Don’t)

If you haven’t reconciled your books since 2021, this is not a cleanup. It’s archaeology.

Why it’s a problem: Years of uncategorized transactions don’t resolve themselves overnight.

Fix it: Call in a professional for a bookkeeping catch-up. And maybe apologize in advance.

4. Confusing a Chart of Accounts with a Chart of Astrology

COGS isn’t your rising sign. It’s Cost of Goods Sold—and no, “Mercury in retrograde” is not why your expenses are high.

Why it’s a problem: If you don’t understand what your numbers mean, you’re flying blind.

Fix it: Learn the basics (or work with someone who won’t make you feel dumb for asking—(like me).

5. Waiting Until Tax Season to Hit the Panic Button

Every year around April 10th, my inbox turns into a war zone.“Rob, can we get everything done by tomorrow?”

Spoiler: No. No, we cannot.

Fix it: Stay on top of things monthly. Book a quarterly review. Avoid tax panic altogether.

Final Thoughts (and a Mild Cry for Help)

Bookkeeping doesn’t have to be painful. It doesn’t have to involve panic or paper cuts. It just has to be done consistently—and ideally with someone who gets it.

Like me.

📌 I’m Rob Schaublin-Yanes, founder of R. Schaublin & Associates. I help small business owners clean up their books, stay on top of their finances, and breathe a little easier.