Most business owners asking this question already know the answer involves either doing the work themselves or hiring someone. The real question is figuring out which path makes sense and what to do first.

Start by not making it worse. If you’re still running transactions through accounts you can’t reconcile, you’re adding to the pile. Set up a simple system now, even if it’s just a dedicated business bank account and credit card, so new transactions are clean while you sort out the past.

Gather what you have. Bank statements, credit card statements, receipts, invoices, contracts. You probably can’t find everything, and that’s okay. Bank and credit card statements can reconstruct most transactions even if the original documentation is gone. Most financial institutions provide at least two years of statements online.

Assess how far back the problem goes. One quarter behind is manageable for most people willing to put in the time. A full year is a significant project. Multiple years of neglected books is typically a job for virtual bookkeepers in New Mexico or wherever you’re located, unless you have nothing else to do for a few weeks.

Figure out what “messy” actually means in your case. Books can be messy in different ways. Transactions might not have been entered at all. They might have been entered but never categorized properly. Categories might exist but not match how you actually run the business. Bank accounts might not have been reconciled so you don’t know if everything’s there. Personal and business expenses might be mixed together. Each of these requires a different approach.

If you’re going to tackle it yourself, work backward from the present. Get the most recent month clean, then the month before that. Working backward keeps you connected to transactions you actually remember. Going forward means you’re starting with the oldest, most forgotten transactions and losing momentum before you reach anything current.

If the thought of sorting through a year of transactions makes you want to close the browser tab, that’s useful information. A bookkeeper who handles catch-up bookkeeping can often clean up a year of neglected books in a fraction of the time it would take you. They’ve seen the patterns before and have systems for processing large volumes of transactions efficiently.

The real value in getting books cleaned up isn’t just having accurate numbers for last year. It’s being able to make decisions going forward with financial data you can trust. If your books are a mess, you’re running your business on gut feel. That works until it doesn’t.

Once the cleanup is done, decide how you’ll keep it from happening again. That might mean monthly bookkeeping help, a weekly habit of entering transactions yourself, or just better systems for capturing receipts and tracking expenses. The cleanup is a one-time project. The maintenance is ongoing, and that’s where habits matter more than heroic efforts.