Tax season 2027 checklist: you PAY estimated tax (you don’t “file” quarters)
How TY2026 prep / 2027 filing fits together for W-2 + 1099 + Form 1040-ES, with official IRS starting links.
Tax season 2027 · Prep late 2026 / file in 2027 for TY2026
January 2027 filing-season hub + $29 Excel workbook compiled by Shortell Designs.
Confused about W-2 + 1099 together? Prep TY2026 records now. Plain-language IRS-cited guides plus a real Excel workbook for mixed W-2 + 1099 sole props. Not tax advice. Not a filed form. Not IRS approved.
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Get the $29 Excel kit on GumroadExcel workbook · TY2026 · no macros · instant download. Not tax advice.
8 tabs · no macros · print for your CPA · verify on IRS.gov
Form 1040-ES is how you pay estimated tax during the year — you do not “file” a quarterly return. See the tax season 2027 checklist: you PAY estimated tax (you don’t “file” quarters) and the 2026 Form 1040-ES quarterly due dates. Workbook only: Get the $29 Excel kit on Gumroad.
Start with the tax season 2027 checklist: you PAY estimated tax (you don’t “file” quarters), then dig into due dates, who must pay estimated tax, SE / OASDI, and mileage. Dollar rates and safe-harbor tests: confirm on IRS.
How TY2026 prep / 2027 filing fits together for W-2 + 1099 + Form 1040-ES, with official IRS starting links.
Apr 15, Jun 15, Sep 15 2026, and Jan 15 2027 — plus the early-file option. Sourced to Form 1040-ES.
High-level IRS “who / who may not” notes. Thresholds and exceptions: confirm on Form 1040-ES / Pub 505.
How Schedule SE Social Security tax shares the wage base with W-2 Box 3 wages.
Split-year standard mileage for business miles, with IRS notice links.
Eight-tab workbook: income, W-2, expenses, home office, mileage, quarterly 1040-ES reserve, annual summary.
A real Excel workbook for a U.S. sole proprietor who has a W-2 day job and 1099 / gig / freelance income. Not tax advice.
Income 1099. Date, payer, form type, amount, category, year-to-date running SUM.
W-2 Wages. Employer, Box 1 wages, Box 3 Social Security wages; remaining OASDI base so SE Social Security tax is not double-counted against $184,500.
Exact sheet names in W2-1099-Side-Hustle-Kit-2026.xlsx:
SUM.
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Excel workbook with live formulas. Version 2026.1. No VBA, no macros. Instant download after $29 Gumroad checkout. No physical shipping. No subscriptions. Not tax advice.
Get the $29 Excel kit on GumroadSchedule C Expenses. Date, vendor, IRS-style category, amount, deductible formula, notes. Meals limited to 50% automatically.
Home Office. Simplified ($5 / sq ft, max 300 sq ft) vs actual comparison. You choose one method; the selected method feeds profit.
Mileage Log. Date, from, to, business miles, rate used (formula from the trip date), amount, purpose. Split-year rates. Business standard mileage is 72.5 cents per mile from January 1 through June 30, 2026 (Notice 2026-10) and 76 cents per mile from July 1 through December 31, 2026 (Announcement 2026-11 / IRB 2026-29). Enter the trip date; the rate column is a formula.
SE tax + income tax reserve estimate, remaining OASDI base, safe-harbor note, official 2026 due dates.
The Quarterly 1040-ES tab is an estimate of federal self-employment tax and income-tax reserve. It is not a filed IRS form. Verify every constant against current IRS and SSA pages before you pay or file. Pay estimates via IRS Direct Pay or EFTPS, not through this page.
Calendar-year due dates from Form 1040-ES (2026): April 15, 2026; June 15, 2026; September 15, 2026; January 15, 2027. You do not have to make the January 15, 2027 payment if you file the 2026 return by February 1, 2027 and pay the entire balance with the return.
Federal income tax is pay-as-you-go: you pay during the year through withholding, estimated payments, or both (IRS Topic No. 306). With a day job and a side business, you have more than one way to cover the side income. Here are the options the IRS describes:
| Option | How it works | What the IRS says |
|---|---|---|
| More withholding at the day job | File a new Form W-4 with your employer and enter an extra amount to withhold | You may be able to avoid estimated payments on other income this way. Form W-4 has a line for the extra amount (Form 1040-ES 2026; Estimated taxes) |
| Quarterly Form 1040-ES payments | Pay through Direct Pay, EFTPS, your Online Account, card, or check with a voucher | Four 2026 due dates. You can also pay the full amount by April 15, 2026 (Form 1040-ES 2026) |
| Apply last year’s overpayment | Credit part or all of a 2025 refund to 2026 estimated tax | Listed as a payment option in Pub. 505 (2026) |
| A mix of the above | Withholding covers part, estimates cover the rest | Estimated payments aren’t required if withholding in each payment period is at least one-fourth of your required annual payment, or if you’ll owe under $1,000 with your return (Pub. 505 (2026), “Estimated Tax Payments Not Required”) |
The IRS Tax Withholding Estimator can help you decide whether to change your W-4. The workbook’s quarterly tab is a place to write down your own reserve estimate next to these choices. It doesn’t make the choice for you.
Per the IRS, you must pay self-employment tax and file Schedule SE if your net earnings from self-employment were $400 or more. (Church employee income has its own, separate threshold.) Net earnings from a sole proprietorship or independent contracting are generally subject to SE tax (IRS — Self-employment tax).
The same IRS page notes that you can deduct the employer-equivalent portion of your SE tax when you figure adjusted gross income. W-2 employees can’t deduct the Social Security and Medicare taxes withheld from their wages. When you estimate a side-hustle reserve, use the Form 1040-ES worksheet, which includes this deduction. Don’t just apply one flat percentage to profit (Form 1040-ES 2026 worksheet; Pub. 505 (2026), Worksheet 2-3).
SUM, SUMIF, IF, ROUND). No VBA, no macros.State income tax (optional dollar reserve you type); QBI wage / UBIA / specified-service phaseout math (warning only); capital-gain rates; NIIT; AMT; SE health insurance; retirement contribution deductions; most credits; dependents; depreciation schedules; inventory; employees/payroll beyond a W-2 you already received; annualized income installments; farming/fishing 66⅔% estimated-tax rule. It does not file Form 8829, Schedule C, Schedule SE, or Form 1040-ES for you.
Gather these before you fill in any worksheet, whether it’s ours, a tax program’s, or a preparer’s. The IRS notes that business purchases and sales generate supporting documents, and that you must keep records as long as needed to prove the income or deductions on a return (IRS — Recordkeeping).
How long to keep them: the IRS says 3 years in many cases, with longer periods in specific situations. For example, it’s 6 years if you leave out income worth more than 25% of the gross income shown on your return (IRS — How long should I keep records?).
No. The workbook is live formulas only — no VBA, no macros. Works in Microsoft Excel. Sample rows ship so you can inspect formulas, including the July 1 mileage-rate switch.
Yellow cells with blue font are inputs. White cells are formulas. Footer on every sheet: “Not tax advice. Verify with IRS publications and your CPA. © 2026 Shortell Designs.”
Split year. Business standard mileage is 72.5 cents per mile from January 1 through June 30, 2026 (Notice 2026-10) and 76 cents per mile from July 1 through December 31, 2026 (Announcement 2026-11 / IRB 2026-29). Enter the trip date; the rate column is a formula.
$184,500, from the SSA contribution and benefit base and Form 1040-ES (2026). Self-employment Social Security tax (12.4%) shares that annual base with your day-job Box 3 Social Security wages. Remaining base (not below zero) is the maximum side-hustle earnings still subject to the 12.4% SE Social Security tax. Medicare (2.9%) has no wage-base cap.
No. State income tax is not calculated — you may type an optional state reserve. QBI is a simplified 20% estimate (with a $400 floor if active QBI ≥ $1,000, capped at 20% of taxable income before QBI). Wage / UBIA / specified-service limits on Form 8995-A are not applied; a warning appears if taxable income is above the 2026 Form 8995-A draft thresholds.
Neither. Shortell Designs is not a CPA. The Quarterly 1040-ES tab is an estimate of federal self-employment tax and income-tax reserve. Verify every constant against current IRS and SSA pages before you pay or file. Pay estimates via IRS Direct Pay or EFTPS, not through this page.
Calendar-year due dates from Form 1040-ES (2026): April 15, 2026; June 15, 2026; September 15, 2026; January 15, 2027. You do not have to make the January 15, 2027 payment if you file the 2026 return by February 1, 2027 and pay the entire balance with the return.
One Excel workbook for tax year 2026, eight tabs listed above, plus a how-to with IRS / SSA links inside the paid kit. This public page is the sales listing only. The workbook is not hosted here and is not a free download.
Often, yes. Form 1040-ES (2026) says wage earners may be able to avoid estimated payments on other income by filing a new Form W-4 to have more tax withheld. The IRS Tax Withholding Estimator can help you choose an amount (Form 1040-ES 2026; Tax Withholding Estimator).
Not necessarily. Pub. 505 (2026) Table 2-1 says that if you first have income subject to estimated tax after August 31, your first payment is due January 15 of the next year. See the 2026 estimated tax dates guide for the full table (Pub. 505 (2026)).
No. The IRS says you may still owe tax when you file even if you pay the required annual payment. The safe harbor is about the underpayment penalty, not your final balance (Form 1040-ES 2026). Not tax advice. Consult a tax professional or IRS resources for your situation.
Figures in the kit were compiled from these official pages. Always re-check before you pay or file. No affiliates.
Not tax advice. This workbook is a bookkeeping log and an estimate of federal self-employment tax and income-tax reserve. It is not a substitute for IRS forms, IRS publications, or a CPA / enrolled agent who knows your facts. Shortell Designs is compiling this kit — not a CPA, not a tax preparer, and not offering a professional tax service.
Estimates only. Verify every constant against current IRS and SSA pages before you pay estimated tax or file a return. Safe-harbor notes do not guarantee you will owe nothing at filing. Home-office exclusive-use is a legal test you attest by using the sheet (Publication 587). QBI phaseout, state tax, and several other items are intentionally not fully modeled.
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