Free working checklist
The 1099 Transition Kit
Before your first independent shift: compare the offer, confirm the setup, arrange coverage, and make a plan for taxes and records.
Updated October 13, 2026 · No email required
Use these checks while reviewing your contract with your CPA, attorney, and insurance adviser. On-page checks reset when you reload; download a copy to keep your notes.
01Compare the offer
Start with the contract and your actual costs.
02Confirm the business setup
Requirements depend on your profession, state, and work relationship.
03Arrange coverage and credentials
Get the facility's actual requirements before promising a start date.
04Plan taxes and keep records
Reserved cash, estimated tax, and completed payments are different records.
2026 federal estimated payments
Sufficient wage withholding can cover your household requirement. Otherwise, use Form 1040-ES to calculate payments, including withholding, credits, safe-harbor rules, and timing. These are the standard dates; state schedules and disaster relief may differ.
| Income period | Payment due |
|---|---|
| January–March 2026 | April 15, 2026 |
| April–May 2026 | June 15, 2026 |
| June–August 2026 | September 15, 2026 |
| September–December 2026 | January 15, 2027 |
A safe-harbor target can limit an underpayment penalty while leaving a balance due with the return. Payroll filings, entity returns, and retirement elections have their own deadlines. See the calculation and safe-harbor example.
Check eligibility before counting a deduction
A deduction reduces taxable income. It does not reimburse the expense, and it may differ from the cash you paid.
- Professional expenses
- Ordinary and necessary business costs; keep evidence and separate reimbursements and personal use.
- Education and equipment
- Education must meet work-related requirements; equipment may need depreciation or another eligible cost-recovery method.
- Travel and meals
- Confirm tax home and temporary-assignment rules. Eligible business meals are generally limited to 50%.
- Business mileage
- 72.5¢ per mile for January–June 2026; 76¢ for July–December. Ordinary commuting generally does not qualify.
- Home office
- Regular and exclusive business use plus the applicable qualifying-use test. A desk at home is not automatically eligible.
- Health insurance
- Earned-income and plan rules apply. No self-employed deduction for months eligible for subsidized coverage through your or your spouse's employer.
- Retirement
- 2026 employee 401(k) deferral: $24,500 across applicable plans. Overall defined contribution limit: $72,000 before eligible catch-up, subject to compensation and plan rules.
Self-employment tax generally uses 92.35% of business profit. Its Social Security portion shares the 2026 $184,500 wage base with the same person's covered wages. Medicare, QBI, health insurance, and retirement each have separate rules; do not apply a flat tax or deduction percentage to every receipt.