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Are There Better Health Insurance Options for Freelancers in Massachusetts?

By Martin Elefant · Licensed insurance agent · Updated November 2026 · 5 min read

Freelancers in Massachusetts — designers, writers, developers, photographers, musicians — usually buy whatever the Massachusetts Health Connector shows them in November and move on. There's often a better fit.

If your income is modest or variable

The marketplace is probably right, and you may qualify for a larger subsidy than you think once expenses are deducted. Medicaid is expanded (MassHealth) in Massachusetts.

If you've grown past the subsidy line

Successful freelancers hit the 400% cliff and suddenly pay full price. If you're healthy, a private shared-network PPO on Cigna, Aetna and PHCS PPO is priced on your health, not your 1099s — usually 30–50% less, with a national network that travels with you.

If you work across state lines

Marketplace HMOs are local. A national PPO covers you in-network in every state, which matters for freelancers who split time between Massachusetts and somewhere else.

If you have a pre-existing condition

Stay on the marketplace. Private plans underwrite; the marketplace doesn't.

The Massachusetts picture

Massachusetts is one of the most tightly regulated individual markets in the country: the state mandate requires coverage that meets minimum creditable coverage rules, and many non-ACA plans don't. Private options here are narrower than in most states, so the honest answer is usually a careful comparison, not a promise of savings. Massachusetts has a flat 5% state income tax, so the self-employed health premium deduction helps at both the federal and state level.

Check your options — we'll show you both.

ME
Martin Elefant
Licensed insurance agent · NPN 20765405 · Lyons Life LLC · Massachusetts Private Health

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