“Can I deduct this?”
Finally, real answers.
Every expense people actually wonder about — answered in plain English with the IRS citation attached. No hedge-everything disclaimers. Just yes, no, or here’s what it depends on.
Each guide below covers who qualifies, how to claim it, what records you need, and where it goes on your return. Built from IRS publications, not opinion.
Coming Soon
We’re adding new “Can I Deduct This?” guides every week during tax season. Here’s what’s next:
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How We Decide: Yes, No, or It Depends
Every answer in this series comes directly from IRS publications — primarily Publication 535 (Business Expenses), Publication 502 (Medical Expenses), and Publication 529 (Miscellaneous Deductions). When the IRS says yes, we say yes. When it says no, we don’t sugarcoat it. When it depends on your situation, we tell you exactly what it depends on.
The “Ordinary and Necessary” Test
Most business deductions come down to a two-word test from IRS Publication 535: is the expense ordinary (common in your trade) and necessary (helpful and appropriate)? This is why a graphic designer can deduct Adobe Creative Cloud but not Netflix, and why a real estate agent can deduct mileage to showings but not their commute to a fixed office. Context matters — and we explain the context for every expense.
What About W-2 Employees?
If you’re a salaried or hourly employee, most of these deductions don’t apply to you federally — the 2017 Tax Cuts and Jobs Act eliminated the unreimbursed employee expense deduction through 2025. Some states still allow it. If you have a side gig or 1099 income, those expenses follow business rules. We flag this clearly in every guide. See our full business deduction guide for more.
Calculators to Pair with These Guides
Once you know something is deductible, you need to know how much. Use our mileage calculator for vehicle expenses, the home office calculator for your workspace, or the medical deduction calculator to see if you clear the 7.5% AGI threshold.