Start by understanding what you’re dealing with. Receipts prove what you spent money on. Invoices are either bills you received from vendors or bills you sent to customers. These get organized differently, so separating them first saves time.

For receipts, sort them by expense category rather than by date. Office supplies in one pile, meals and travel in another, professional services in a third. Use categories that match your bookkeeping software or that your accountant uses on your tax return. If you don’t know what categories to use, look at your bank statements and see what types of purchases repeat most often.

Paper receipts fade and tear. Scan or photograph them while they’re still readable. Your phone camera works fine. Apps like Dext, Hubdoc, or even just a dedicated folder in Google Drive give you searchable backups. The goal is having a digital copy you can find when needed, whether that’s for your bookkeeper, an audit, or just figuring out what that $127 charge was actually for.

Match your receipts to your bank and credit card statements. This is where most people discover gaps. You have a $200 charge at Home Depot on your statement but no receipt. Or you have a receipt for office supplies but it’s on your personal card instead of the business card. Working with an Andover, MA bookkeeper can help you work through this matching process faster if the backlog is substantial.

For invoices you’ve received from vendors, check which ones are paid and which are still outstanding. Paid invoices should match to payments in your bank records. Unpaid invoices belong on a list you’re tracking until they’re resolved. If you’re not sure whether something was paid, your bank statement will tell you.

For invoices you’ve sent to customers, the same logic applies. Match customer payments in your bank account to the invoices they were paying. Anything unmatched is either a payment you haven’t identified or an invoice that’s still open.

Once the current pile is handled, set up a system so you don’t end up here again. A weekly five-minute habit works better than monthly hour-long sessions. Every Friday, photograph any paper receipts from the week and move them to your digital folder. Review your bank transactions and categorize anything new. Small consistent effort beats annual scrambles.

If the backlog feels overwhelming, catch-up bookkeeping services exist specifically for this situation. You hand over the pile, get your books brought current, and start fresh with organized records and a system that’s already working. The relief of having clean books often pays for itself in reduced stress and better visibility into your business finances.