Going 1099 checklist

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1. Money math

• Run your offers through the W-2 vs 1099 calculator with your real state.
• Write down the breakeven hourly rate and add a cushion for slow months.
• Open a separate business checking account on day one.

2. Tax set-aside

• Create a savings “envelope” or sub-account labeled Taxes.
• Move 25–35% of every client payment into it until you refine the percentage.
• Put IRS quarterly dates on your calendar (Form 1040-ES).
• Check whether your state also wants estimated payments.

3. Paperwork

• Get an EIN (free from IRS) if you want one for banking and forms.
• Send a W-9 to each client that requests it.
• Use a simple contract: scope, rate, payment terms, IP, termination.
• Track mileage and expenses from the first week (photo receipts are fine).

4. Insurance & retirement

• Compare health coverage before your W-2 plan ends (marketplace, spouse, COBRA).
• Ask about liability or malpractice coverage your clients do not provide.
• Open a solo 401(k) or SEP-IRA once income is steady.

5. Quarterly habit

• First week of each quarter: update year-to-date profit in a spreadsheet.
• Pay estimates, then skim the calculator again if your rate or hours changed.
• Keep 3 months of expenses in cash if you can.