The IRS announced a slate of self-service resources and live webinars for National Small Business Week on May 6 (IR-2026-61), running through May 9. The materials are aimed primarily at sole proprietors, gig workers, and small partnerships — the segment of taxpayers most likely to be confused about quarterly estimated payments, self-employment tax, and the 1099 vs W-2 trade-off.
The IRS tools are useful as far as they go, but they tell you what the rules are. They don't show you what those rules mean for your specific income. That's where our calculators slot in. Three to pair with the new IRS resources, in the order we'd run them if you were starting from scratch.
If you're weighing a 1099 contract against a W-2 offer — or trying to figure out what a freelance gig is actually worth compared to a salary — this is the first calculator to run. The 1099 vs W-2 Calculator accounts for the self-employment tax (15.3% on the first $176,100 in 2026, then 2.9% Medicare above that), the half-deduction for the employer-equivalent portion, and the loss of employer benefits like health insurance, retirement match, and PTO.
The short version: a $100,000 1099 contract typically nets you less than a $90,000 W-2 with standard benefits, once you account for the full tax and benefits picture. Our calculator shows the gap for your exact numbers.
Self-employment tax is the part that surprises everyone the first time they file Schedule SE. It's 15.3% on top of regular income tax, and it kicks in once your net self-employment earnings cross $400. The Self-Employment Tax Calculator takes your net profit (gross income minus deductible business expenses), applies the 92.35% adjustment factor required by the IRS, and gives you the actual SE tax owed plus the deductible employer-equivalent portion.
If you're a freelancer who hasn't run these numbers, this is where most surprise tax bills come from. Better to see the number now than in April.
The IRS Tax Withholding Estimator updates announced this week are aimed primarily at W-2 filers. Self-employed filers don't have withholding — they have quarterly estimated payments due mid-April, mid-June, mid-September, and mid-January. Miss them and you owe an underpayment penalty even if you pay everything by the April 15 filing deadline.
The Quarterly Tax Calculator projects your annual federal income tax plus SE tax, divides it across the four quarters using the IRS safe-harbor rule, and gives you the exact amount to set aside each quarter. Pair that with a separate business savings account and you've solved the single biggest cash-flow problem self-employed workers face.
Run the 1099 vs W-2 tool to confirm a gig is worth taking. Run the SE tax tool the moment your year-to-date net income hits roughly $5,000 so the number doesn't sneak up on you. Run the quarterly tool each quarter to size your estimated payment. Three tools, fifteen minutes total, and your tax surprise season ends.
Make Small Business Week useful. Pair the new IRS resources with our 1099 vs W-2 Calculator, Self-Employment Tax Calculator, and Quarterly Tax Calculator to see what the rules mean for your actual income.
Related tools: 1099 vs W-2 Calculator · Self-Employment Tax Calculator · Quarterly Tax Calculator · Freelance Rate Calculator · Profit Margin Calculator