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If you're self-employed, every business expense you can properly categorize and document is a deduction you can actually use on Schedule C (or your bookkeeping software of choice). The hard part isn't the tax math — it's turning a few hundred cryptic line items like "SQ *JOES COFFEE" or "POS DEBIT 4471 AMAZON.COM" into categories a tax preparer or piece of software recognizes.
Most gig-work and small-business spending falls into a short list of buckets. Keeping your own categories consistent with these makes tax time and monthly bookkeeping much faster:
| Category | Typical transactions |
|---|---|
| Vehicle / Fuel | Gas stations, rideshare driver fuel, tolls, parking |
| Supplies | Amazon, office supply stores, Costco business runs |
| Phone / Internet | Carrier bills, internet/cable used for work |
| Software / Hosting | SaaS subscriptions, domains, cloud hosting, AI tools |
| Insurance | Business, liability, or vehicle insurance for work use |
| Meals | Client meals, work-travel food (often only partly deductible — check current IRS rules) |
| Rent / Office | Coworking space, studio, storage unit for inventory |
| Taxes | Estimated quarterly payments, state filing fees |
| Transfers | Venmo/PayPal/Zelle moves that aren't really expenses — flag and exclude these |
Doing this by hand is fine for a dozen transactions and painful for a few hundred. The description text banks give you is inconsistent (merchant codes, truncated names, processor prefixes like "SQ *" or "POS DEBIT"), so simple find-and-replace rules only get you partway before you're stuck eyeballing every odd line individually.
Statement Sorter takes the CSV you already exported, applies the same category logic above automatically, and uses an AI pass to catch the transactions plain rules miss — then hands you back a categorized CSV with totals per category. No bank login, no signup, free while in beta.
Try it on your statement →Any first-pass categorizer — manual or automated — should be reviewed before you file. This guide and the linked tool are meant to save you the tedious first sort, not to replace a bookkeeper, CPA, or your own judgment about what's actually deductible for your situation.