Health Insurance for Self-Employment

Going Self-Employed: Coverage Before You Leap

Line up coverage before your last day

Leaving a job to work for yourself ends employer coverage and opens a 60-day special enrollment window. The smoothest transitions start shopping two to four weeks before the last paycheck, so the new plan starts the day the old one ends.

Budgeting the premium into your rates

Employees never see the full cost of coverage; employers quietly pay most of it. As your own boss, build the real premium into your pricing. Many self-employed people can deduct premiums, which softens the true cost. Confirm specifics with your tax professional.

Income estimates when income is new

Marketplace subsidies run on estimated annual income, which is hard to guess in year one. We help you set a defensible estimate and adjust mid-year if the business takes off, so tax season holds no surprises.

Once you're covered and running your business, the ongoing questions, income swings, tax deductions, HSA options, business structure, are covered in full in our Self-Employed Health Insurance guide. This page focuses specifically on the exit from employer coverage; that one covers the ongoing decisions after you're already self-employed.

The Job-Exit Coverage Checklist

• Confirm your exact last-day-of-coverage date with HR, not just your last day of work.
• Start shopping 2-4 weeks before your last day so a new plan can begin the day the old one ends.
• Refill any prescriptions while still on employer coverage, if your timeline allows.
• Estimate your first-year business income as realistically as possible for your Marketplace application.
• Confirm your must-keep doctors are in-network on any new plan you're considering.
• Enroll within your 60-day Special Enrollment Period to avoid a coverage gap.