Health Insurance for the Self-Employed

Practical guides on individual health coverage, written for founders, contractors, and independent professionals who are responsible for their own coverage decisions.

Small Business10 min read

Health Insurance for Small Businesses: The Business Case, Real Costs, and Your Options

Why offering coverage matters despite rising costs — talent retention data, 2026 premium reality, tax advantages, and alternatives like ICHRA and QSEHRA explained side by side.

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Plan Types7 min read

ACA Marketplace vs Private PPO: Which Is Right for Self-Employed Professionals?

The ACA Marketplace offers subsidies that can dramatically lower your net cost. Private PPOs offer broader networks and no subsidy cliff. Here is how to decide which path fits your income, health, and situation.

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Plan Types5 min read

Why COBRA Is Almost Never the Right Long-Term Answer

COBRA converts your $150 payroll deduction into an $800+ monthly bill. For most self-employed professionals, individual market alternatives cost significantly less for equivalent coverage.

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Tax Strategy8 min read

The HSA Advantage: How to Use a High-Deductible Plan to Build Tax-Free Wealth

HSAs offer a triple tax advantage that's rare in U.S. tax law. When used as an investment vehicle instead of a spending account, an HDHP plus HSA can outperform traditional plans over a career.

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Plan Types6 min read

Health Sharing Plans Explained: What They Are and What They Won't Cover

Health sharing arrangements aren't insurance and operate under different legal rules. Understanding what they cover and what they exclude is essential before you rely on one for major medical.

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Cost Structure5 min read

Deductible vs. Out-of-Pocket Maximum: What the Difference Costs You

Your deductible and your out-of-pocket maximum are two different numbers that interact in a specific sequence. The gap between them can cost thousands in a major claim year.

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Using Your Coverage4 min read

How to Read an Explanation of Benefits (EOB)

An EOB isn't a bill, but it tells you exactly how your insurer processed a claim. Knowing how to read one helps you catch billing errors and understand your actual liability before the bill arrives.

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Have a specific question?

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