Health insurance for freelancers and the self-employed

Leaving W-2 employment means leaving the only part of health insurance that was ever easy: not having to think about it. Here's the whole map, in the order you'll need it.

Your enrollment window starts when your old coverage ends

Losing employer coverage is a qualifying life event. You get a 60-day special enrollment period from the day your old plan ends (and you can enroll up to 60 days before, to avoid any gap). Outside that window, you wait for open enrollment — November 1 to December 15, 2026 for 2027 coverage. Don't spend week one of freelancing designing a logo. Spend an hour on this.

The subsidy is real money — if you estimate income honestly

Your premium tax credit is based on your estimated MAGI for the coverage year — not last year's W-2, not last month's invoice. For a freelancer that estimate is genuinely hard: income is lumpy, and the figure that matters is net self-employment income (after business expenses), plus any other household income.

Three rules keep you safe:

1. Estimate the year, not the month. Annualize conservatively from signed contracts, then adjust as reality arrives.
2. Report changes within the month they happen. A big new client in June should change your subsidy in June, not surprise you next April.
3. Respect the reconciliation. Your credit is squared up on your tax return, and starting with plan year 2026 the repayment caps were eliminated — underestimate badly and the entire overpayment comes due. The worked examples live in how to estimate self-employment income.

The deduction most freelancers forget

If you have net self-employment profit, premiums you pay (after any subsidy) are generally deductible above the line via the self-employed health insurance deduction — no itemizing required. That interacts with your MAGI, which interacts with your subsidy; the deduction guide untangles the circularity in plain English.

Picking the plan itself

• Keep your doctors: filter by provider in the enrollment flow before comparing prices — a cheap plan that excludes your OB-GYN isn't cheap.
• Metal tiers are cost-sharing math, not quality ratings. High-deductible Bronze plus a funded HSA suits high-variance income; Silver unlocks cost-sharing reductions at lower incomes; because of how Silver is priced ("silver loading"), Gold can sometimes beat Silver.
• Never assume last year's answer. Premiums moved more in 2026 than any year since 2018, and 2027 filings point the same direction.

The 30-second version

Losing coverage gives you 60 days. Estimate income for the year ahead, honestly. Take the subsidy you qualify for, report changes promptly, deduct what you pay, and check your actual number below — it's faster than reading another paragraph.