5 Habits That Make Things Harder For your Bookkeeping Processes

You’re careful with your business. You try to stay organized. So why does your bookkeeping still feel like a mess? It might not be about how much work you’re doing—it might be how you’re doing it.

Some of the most frustrating bookkeeping problems come from habits you don’t even realize are causing trouble.

Most business owners already know not to mix personal and business expenses—but here are some less obvious habits that quietly make bookkeeping harder, less accurate, and more expensive over time:

1. Using “Cash App” or Venmo Without Business Context
Sending money via Venmo or Cash App might feel fast and easy—but without clear labels, bookkeeping becomes a guessing game.

Example: You send $250 to a contractor but write “Thanks!” in the note. There’s no invoice, no context, and no backup. Come tax time, no one remembers what it was for—or worse, it’s categorized wrong.

What to do instead: Use payment tools that allow memos or are linked to an invoicing system. Always include what it was for and the service date. Better yet, use tools that integrate directly with your books.

2. Reimbursing Employees Without a Paper Trail
Handing an employee $100 for “supplies” and calling it a day? That’s a recordkeeping nightmare waiting to happen.

Example: Your assistant picks up printer ink and some pens from Office Depot and you pay them back with a Zelle transfer. But there’s no receipt, and no documentation in your books that the $100 wasn’t just a bonus or random payout.

What to do instead: Set up a simple reimbursement form and require receipts. If it’s frequent, use an expense card or tool like Expensify.

3. Depositing Personal Refunds or Rebates Into Your Business Account
This one throws off income reporting—and it’s more common than you’d think.

Example: You get a $200 Costco rebate check from personal purchases and deposit it into your business account. Now your books show an unexplained $200 in income.

What to do instead: Keep business deposits clean. If you accidentally deposit something personal, flag it right away so your bookkeeper can classify it correctly as owner equity, not income.

4. Holding Payments Until You “Catch Up” on Invoicing Delaying invoices until you’re caught up can distort revenue, especially for accrual-based accounting.

Example: You did work in April, but didn’t send the invoice until July. Your books now reflect income at the wrong time—so cash flow reports, profitability, and forecasting are all off.

What to do instead: Use a recurring invoicing tool or block out time weekly to bill. Timely invoicing isn’t just about getting paid—it keeps your books accurate.

5. Renaming Transactions in Your Bank Feed Without Consulting Your Bookkeeper QuickBooks gives users the power to rename transactions—but that power can backfire.

Example: You rename “Amazon Marketplace” to “Office Supplies,” but the purchase was actually inventory. You’ve now miscategorized COGS as an expense, which impacts tax reporting and your margins.

What to do instead: Ask before renaming—or leave a memo for your bookkeeper and let them categorize with context.

Are You Accidentally Making Things Harder? These aren’t “bad” habits—they’re just easy mistakes that snowball over time. And they can make even the most organized business feel chaotic.

If your bookkeeping still feels messy, overwhelming, or confusing, let’s fix that. Connect with us for a free bookkeeping assessment and find out what’s working—and what might be holding your books back.