The Freelancer’s Guide to Health Insurance in the U.S.

[cryptohog]

One of the biggest hurdles for U.S.-based freelancers? Health insurance. In my first year, navigating coverage while managing knee surgery taught me how critical it is to plan ahead.

We balanced seasonal insurance from my spouse’s job with COBRA coverage during the off-season—costing about $3,000/month for a family of three. This year, we switched to the open market, dropping costs to around $1,000/month.

Key takeaways:

Work with a local, knowledgeable insurance broker.

Always verify providers are actually in-network (websites can be outdated).

Consider life events carefully—they can qualify you for off-cycle coverage.

Insurance is a crucial part of making freelancing sustainable, and careful planning ensures you stay covered without breaking the bank.

[Abdul Khan]

Health coverage is often pricier than expected, but choosing a plan that matches your actual medical needs can prevent huge out-of-pocket shocks later.

[Rimon Khan]

Factoring insurance into your freelance rates is essential—treat it as a business expense, not a personal afterthought, to stay sustainable long-term.