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.

State Guides·April 10, 2026·5 min read

Health Insurance for Freelancers in Texas: 2026 Guide

Texas has no state exchange and no expanded Medicaid, which pushes more freelancers toward private options.

State Guides·April 8, 2026·5 min read

Health Insurance for Freelancers in Florida: 2026 Guide

Florida has the highest marketplace enrollment in the country, and a large gig economy that sits outside it.

State Guides·April 5, 2026·4 min read

Health Insurance for Freelancers in Tennessee: 2026 Guide

What is actually available to a self-employed Tennessean, and how to compare it honestly.

State Guides·April 3, 2026·4 min read

Health Insurance for Freelancers in Georgia: 2026 Guide

Georgia runs its own exchange now, and the options look different depending on whether you are in metro Atlanta.

State Guides·March 30, 2026·4 min read

Health Insurance for Freelancers in North Carolina: 2026 Guide

North Carolina expanded Medicaid in 2023, which changed the picture for lower-income independents.

Savings·March 28, 2026·6 min read

The Cheapest Health Insurance for Self-Employed People in 2026

Cheapest premium and cheapest year are different questions, and confusing them is expensive.

Savings·March 24, 2026·4 min read

How Much Does Health Insurance Cost for a 1099 Contractor in 2026?

Real numbers, and the three variables that move them most.

Working Owners·March 21, 2026·5 min read

Can One Person Get Group Health Insurance? Yes, Here's How

Traditional small-group insurance wants two employees. There is a route that does not.

Plan Types·March 20, 2026·5 min read

PPO vs HSA vs EPO: Which Health Plan Fits a Freelancer?

Three labels that get used interchangeably and mean quite different things for your wallet.

Savings·March 17, 2026·6 min read

ACA Alternatives for 1099 Workers: 5 Real Options Compared

Every alternative to the marketplace has a specific trade-off. Here they are, stated plainly.

Working Owners·March 12, 2026·6 min read

How to Get Health Insurance Without an Employer (2026)

A step-by-step order of operations, cheapest realistic option first.

Savings·March 12, 2026·4 min read

Is a Group Health Plan Cheaper Than the ACA Marketplace?

The honest answer depends on your subsidy, your age, and how much care you actually use.

Taxes·March 7, 2026·5 min read

The Self-Employed Health Insurance Tax Deduction, Explained

An above-the-line deduction that a lot of freelancers either miss or claim incorrectly.

Working Owners·March 5, 2026·4 min read

Do You Qualify for a Group Health Plan as a Business of One?

The eligibility rules are simpler than most people expect, and for these plans there is no health questionnaire.

Working Owners·March 2, 2026·5 min read

Best Health Insurance for Gig Workers: Uber, DoorDash, and Instacart Drivers

Platform work rarely comes with benefits, and the partnerships that exist are thinner than they sound.

Plan Types·March 1, 2026·4 min read

Reference-Based Pricing, Explained for Independents

You will see RBP plans advertised at very low premiums. Here is the mechanism, and the risk.

Savings·February 27, 2026·4 min read

COBRA After Leaving a Job: Is It Worth It for the Self-Employed?

COBRA keeps your exact plan and your exact doctors. It also costs what your employer was hiding from you.

Savings·February 25, 2026·5 min read

Group Health Insurance vs Marketplace: The Real Difference

Not a price comparison. A structural one, because the two work in genuinely different ways.

Working Owners·February 20, 2026·4 min read

Health Insurance for Small Business Owners With No Employees

What is available when the business is just you, and what changes the day you hire someone.

Savings·February 14, 2026·5 min read

When to Leave COBRA and Switch to a Self-Employed Health Plan

COBRA is expensive but sometimes correct. Here is how to tell which situation you are in.