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Insurance Insights & Guides
Plain-English guides on health, dental, vision, supplemental, and family insurance — written by licensed agents who do this every day.
Transition
Health Insurance Options When You Leave a W-2 Job to Freelance
The 60-day window after you quit is the most valuable enrollment period you'll ever have. Here's exactly what to do with it.
8 min readRead article →
Cost & PricingHow Much Does Health Insurance Cost for the Self-Employed in 2026?
Ranges, not averages. Here's what freelancers, contractors, and small-business owners of one actually pay in 2026 — before and after subsidy.
7 min readRead article →
Open EnrollmentACA Open Enrollment 2026 for Freelancers: What's Different This Year
Enhanced subsidies are still in effect for 2026. Here's the freelancer's Open Enrollment guide — dates, deadlines, and what's changed.
6 min readRead article →
Tax StrategyHSA + HDHP Strategy for 1099 Workers: The Triple-Tax-Advantaged Playbook
Pair a High Deductible Health Plan with an HSA and you unlock the only triple-tax-advantaged account in the U.S. tax code. Here's how self-employed people use it.
7 min readRead article →