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Tips3 min read·

The Simple Receipt & Record-Keeping System That Actually Works

Stop shoving receipts in a drawer and hoping for the best. This straightforward system takes 10 minutes a week and will save you hours come tax season.

By Cherokee Bookkeeping Team

The most common bookkeeping pain point we hear from clients isn't complicated — it's receipts. Paper ones, digital ones, email ones, phone screenshots. They pile up and then disappear exactly when you need them. Here's the simple system we recommend to clients. THE CORE PRINCIPLE: CAPTURE IMMEDIATELY, FILE ONCE A WEEK Don't let receipts accumulate. The moment a transaction happens, capture it. Then spend 10 minutes each week filing what you've captured. STEP 1: CHOOSE ONE CAPTURE METHOD Pick one and stick with it: - A free app like Expensify, Dext, or even Google Drive with a "Receipts" folder - A dedicated email address (like receipts@yourbusiness.com) that you forward all digital receipts to - A small accordion folder if you prefer paper STEP 2: CATEGORIZE AS YOU GO When you save a receipt, tag it with a category: Office Supplies, Travel, Meals, Software, etc. Doing this in real time takes 10 seconds. Doing it in bulk six months later takes hours. STEP 3: WEEKLY 10-MINUTE REVIEW Every Friday (or whatever day works), spend 10 minutes: - Forwarding any receipts you missed to your capture system - Confirming transactions in your bookkeeping software match what you captured - Flagging anything that looks off WHAT THE IRS ACTUALLY REQUIRES For most expenses, you need: the amount, the date, the vendor, and the business purpose. A photo of a receipt plus a quick note ("team lunch — client meeting") is sufficient. THE PAYOFF When tax season arrives, you'll have a complete, organized record of every business expense — and you'll claim every deduction you're entitled to. That's money back in your pocket.

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