Health Insurance—The Hardest Part of Freelancing in the U.S.
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If you freelance in the U.S., health insurance is the elephant in the room. Unlike countries with universal coverage, insurance here is expensive, complex, and often the biggest barrier to going independent. In my case, we relied partly on my spouse’s seasonal employer insurance and partly on temporary solutions like COBRA—an option that can easily cost thousands of dollars per month.
Eventually, we moved to the open market, cutting our premiums significantly but accepting weaker coverage. The key lesson? There’s no universally “right” choice—only trade-offs. Anyone navigating this should work with a local insurance broker who actually understands which providers accept which plans. Marketing websites are often wrong, and learning that the hard way is both stressful and expensive.
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layoffs really exposed how conditional loyalty actually is, no matter how good u are