Notes on group health for the self-employed.
Short reads that cover what actually matters when you're picking a plan outside the W-2 world.
Health Insurance for Freelancers in Texas: 2026 Guide
Texas has no state mandate and one of the highest uninsured rates in the country. Here's what freelancers and 1099 workers can actually buy in 2026.
Health Insurance for Freelancers in Florida: 2026 Guide
Florida has the second-highest uninsured rate for self-employed workers. Here's what freelancers, consultants, and 1099 contractors can pick from in 2026.
Health Insurance for Freelancers in Tennessee: 2026 Guide
PSM and PSN of Tennessee are headquartered in the state, which makes Tennessee one of the best places in the country to be a self-employed buyer.
Health Insurance for Freelancers in Georgia: 2026 Guide
Georgia's marketplace is expensive and Medicaid is tightly limited. Here's how freelancers, 1099 contractors, and small business owners can find cheaper coverage.
Health Insurance for Freelancers in North Carolina: 2026 Guide
North Carolina expanded Medicaid in 2023, which changed the math for lower-income freelancers. Here's what 1099 workers should look at in 2026.
The Cheapest Health Insurance for Self-Employed People in 2026
What's actually the cheapest health insurance if you work for yourself? A ranked breakdown by real total cost, not just the headline premium.
How Much Does Health Insurance Cost for a 1099 Contractor in 2026?
National averages, what drives the number up or down, and how to get an accurate estimate for your situation without handing over your email.
Can One Person Get Group Health Insurance? Yes, Here's How
Group health insurance for one person sounds like a contradiction. It isn't. Here's what Working Owner groups are, and why they exist.
PPO vs HSA vs EPO: Which Health Plan Fits a Freelancer?
Plain-English guide to the three letter soups and when each one is the right call for self-employed people.
ACA Alternatives for 1099 Workers: 5 Real Options Compared
Not every self-employed worker is a good fit for Healthcare.gov. Here are five ACA alternatives for 1099 workers, with the math and the tradeoffs.
How to Get Health Insurance Without an Employer (2026)
Five ways to get health insurance when you don't have an employer plan: marketplace, group, spouse's plan, parent's plan, and COBRA.
Is a Group Health Plan Cheaper Than the ACA Marketplace?
Why working owners typically save 25% to 45% vs Healthcare.gov, and what's actually driving the difference.
The Self-Employed Health Insurance Tax Deduction, Explained
You can deduct your premiums above the line if you're self-employed. Here's who qualifies, what counts, and how it works with a group plan.
Working Owner Eligibility: Do You Qualify for Group Health?
Who can actually enroll: 1099 contractors, freelancers, gig workers, self-employed owners, and some W-2s.
Best Health Insurance for Gig Workers: Uber, DoorDash, and Instacart Drivers
Gig platforms don't offer health insurance. Here's what Uber, Lyft, DoorDash, Instacart, and Amazon Flex drivers should actually pick in 2026.
Reference-Based Pricing, Explained for Independents
Why RBP plans have the cheapest premium of the bunch and what the tradeoff is.
COBRA After Leaving a Job: Is It Worth It for the Self-Employed?
COBRA keeps your old plan but at full price plus admin. How it stacks up against working owner group health.
Group Health Insurance vs Marketplace: The Real Difference
Group plans and the ACA marketplace look similar on the surface. Under the hood they're priced completely differently, and that's where the savings come from.
Health Insurance for Small Business Owners With No Employees
Solo business owners can't enroll in a traditional SHOP small-group plan. Here's what you can actually get in 2026 if it's just you.
The $10 Monthly Survey: Why It Makes Group Health Possible
Why every Working Owner member fills out a 2-minute survey each month, and what it has to do with getting group rates.
When to Leave COBRA and Switch to a Self-Employed Health Plan
COBRA is a useful bridge, but it's expensive. Here's when to switch to a cheaper self-employed health plan and how to time the transition.