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Insurance for the Self-Employed & Newcomers

When no employer hands you a benefits package, every kind of coverage becomes your decision. These guides cover health insurance, HSAs, dental and vision, disability, and liability — what you actually need, what you can skip, and how to avoid overpaying.

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Best Health Insurance Options for the Self-Employed, Compared

The main health insurance options for the self-employed compared: Marketplace plans, spouse's coverage, associations, COBRA, and Medica…

11 min read
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Dental and Vision Insurance for the Self-Employed

Is dental and vision insurance worth it for freelancers? How these plans work, what they actually cover, when they save money, and the …

11 min read
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Disability Insurance for Freelancers

Why disability insurance matters more for freelancers than almost anyone: how it works, short-term vs long-term, own-occupation vs any-…

12 min read
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Health Insurance for Freelancers & the Self-Employed

The complete guide to health insurance for freelancers and the self-employed: where to buy it, how Marketplace subsidies and HSAs work,…

12 min read
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HSA Explained

What a Health Savings Account (HSA) is, how the triple tax advantage works, who's eligible, how freelancers should use it, and how it c…

11 min read
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Liability Insurance for Freelancers: What You Actually Need

A clear guide to liability insurance for freelancers: professional liability vs general liability, what each covers, who needs it, what…

12 min read