Most business owners run into these bookkeeping issues at some point — it’s completely normal. What matters is fixing the root of the problem so your numbers start working for you instead of against you. When your books are clean, categorized correctly, and reconciled every month, you get clarity, confidence, and control over your business again. If you ever need help getting everything organized or want someone to maintain it so you can focus on running your business, I’m here to help

1. Not Knowing Where the Money Is Going

Uncategorized expenses, missing receipts, and unclear spending patterns make it hard to track cash flow or identify waste.

2. Falling Behind on Bookkeeping

Books get neglected for weeks or months, creating messy backlogs that are stressful and costly to fix.

3. Mixing Personal and Business Finances

Co-mingled accounts make tax reporting inaccurate and increase the chance of an audit flag.

4. Incorrect or Outdated Categorization of Transactions

Misclassified income and expenses lead to wrong reports, overstated taxes, or missed deductions.

5. Not Reconciling Bank and Credit Card Accounts

Unreconciled statements hide errors, double charges, missing deposits, and even fraud.

6. Poor Cash Flow Visibility

Business owners can’t see upcoming obligations, leading to late payments, overdraft fees, or running out of cash unexpectedly.

7. No Financial Reports or Inconsistent Reporting

Without accurate Profit & Loss, Balance Sheet, and Cash Flow reports, owners operate blindly.

8. DIY Bookkeeping Errors

Inexperienced self-bookkeeping often results in mispostings, duplicates, or gaps that cost more to fix later.

9. Payroll Mistakes

Late payroll, incorrect withholdings, and unfiled payroll taxes create IRS penalties and employee frustration.

10. Sales Tax Confusion

Misunderstanding what products/services are taxable leads to overpayment or (worse) underpayment with penalties.

11. Not Tracking Receivables & Payables

Uncollected invoices and unpaid bills disrupt cash flow and damage vendor/client relationships.

12. Poor Recordkeeping for Tax Season

Missing receipts, unsupported expenses, and sloppy data create stressful tax prep and higher accountant fees.

13. Inaccurate Inventory Tracking

For product-based businesses, untracked inventory causes shrinkage, stockouts, and distorted COGS.

14. Using the Wrong Accounting Method (Cash vs Accrual)

The wrong method can distort profit and create tax surprises.

15. Not Backing Up Accounting Files or Using Outdated Software

Lost data or unsupported software leaves the business exposed to major risks.

16. Lack of Audit-Ready Books

When financials aren’t clean, consistent, and properly documented, IRS or lender audits become stressful and expensive.

17. No Separation of Duties (Risk of Internal Fraud)

One person controlling everything—receipts, payments, reconciliation—increases the risk of employee theft.

18. Not Knowing What Deductions They’re Allowed to Take

Businesses often overpay taxes because they don’t take advantage of allowable deductions.

19. Overcomplicated Charts of Accounts

Too many categories make reporting chaotic and inconsistent over time.

20. No Budgeting or Financial Planning

Owners don’t set financial goals or monitor progress, so profits disappear without explanation.