Bookkeeping and payroll for small businesses across central Virginia.

Call / Text: (866) 478-7426

I'm months behind on my bookkeeping. Where do I start?

Start by taking a breath. Falling behind on bookkeeping happens to most small business owners at some point. The books can be fixed. The question is how to approach it without making things worse or burning a weekend only to realize you’re still lost.

Check for immediate deadlines first. Quarterly estimated taxes, sales tax filings, payroll deposits, a loan application that needs financials. If something is due in the next few weeks, that drives your priorities. Handle urgent items first, even if the rest of the backlog waits another week.

Gather your source documents. Bank statements, credit card statements, invoices, receipts. You need the raw data before you can do anything useful. Download statements from your bank’s website for every month you’re behind. If you use accounting software, make sure it’s connected to your bank feeds so transactions can import automatically. If you’re not sure where to start with organizing everything, talking to a Tri-Cities bookkeeper can help you figure out what’s actually needed.

Start with the oldest month and work forward chronologically. Starting with last month feels more natural, but it creates problems when transactions span multiple months or when you need to fix something early that affects later records.

Bank reconciliation is your first real task. Match every transaction in your bank account to an entry in your books. If you’re using QuickBooks or similar software, this is the core process that tells you whether your records are accurate. Don’t skip ahead to reports or analysis until reconciliation is done for each month.

Code transactions as you go. Every expense needs a category. Every deposit needs an explanation. Miscellaneous is not a strategy. If you don’t know what something was, check the vendor name, look up old emails, or mark it for review rather than guessing.

Decide whether to do this yourself or get help. A few months behind with clean bank statements and simple transactions might take a weekend of focused work. Six months or more behind with multiple accounts, payroll complications, and unclear records probably needs professional catch-up bookkeeping help. The time you spend struggling is time away from running your business.

The goal isn’t perfection. It’s getting to a point where your books reflect reality well enough to make decisions, file taxes accurately, and move forward. Once you’re caught up, staying caught up is much easier than digging out again.

Greater Richmond's Small Business Bookkeeper

The Next Step:
A Short Conversation

Fifteen minutes to tell us what you're dealing with. We'll let you know how we can help and give you a clear price quote.

More Questions

How do I reconcile my accounts in QuickBooks Online?

Reconciliation compares your QuickBooks records to your bank statement. Start with your statement ending date and balance, then match transactions one by one until the difference is zero.

Read answer

Why aren't my bank transactions importing correctly into QuickBooks?

Bank feed issues usually come from broken connections, duplicate handling, or account matching problems. The fix depends on whether transactions aren't showing up at all, appearing twice, or landing in the wrong place.

Read answer

My Last Bookkeeper Left My Books in Bad Shape. Can You Fix Them?

Yes. Cleaning up after a previous bookkeeper is a significant part of what we do. Misclassified transactions, unreconciled accounts, missing records. We sort it out and get you back to accurate books.

Read answer

Can my accountant access my QuickBooks file?

Yes, and you should set this up. QuickBooks Online includes a free accountant user slot specifically for this purpose. QuickBooks Desktop requires sharing the file directly or sending an accountant's copy.

Read answer

What Restaurant Expenses Are Tax Deductible?

Almost everything you spend to run the restaurant is deductible. Food costs, labor, rent, equipment, supplies, marketing, even the music license. The key is tracking it properly and categorizing it correctly.

Read answer

What's the best way to handle cash management in a restaurant?

Start with consistent register banks and count cash at every shift change. Reconcile to your POS daily, deposit frequently, and limit who handles cash to create clear accountability.

Read answer

Virginia bookkeeping firm focused on small businesses. Bookkeeping, payroll, and fractional CFO services from a local Richmond team. A decade of working with businesses like yours. QuickBooks ProAdvisor certified.

Client Reviews

5-Star Rated Firm

Social

  • Intuit ProAdvisor Gold tier certification badge
  • Intuit Certified QuickBooks Level 1 ProAdvisor badge
  • Intuit Certified QuickBooks Level 2 ProAdvisor badge
  • Intuit Certified QuickBooks Payroll ProAdvisor badge

© 2026 Tri-County Bookkeeping LLC