Health Insurance for the Self-Employed

If you work for yourself, nobody hands you a benefits packet. You are the HR department, and health insurance is the single most expensive decision on that list.

I am a licensed health insurance advisor in 31 states. Most of my clients are self-employed: contractors, consultants, freelancers, agents, and small business owners with no employees. Here is how the options actually compare.

You have four real options

The Marketplace. HealthCare.gov or your state’s exchange. Guaranteed acceptance regardless of health history, and the only option where a subsidy can lower your premium. For most self-employed people earning under the subsidy threshold, this is the right answer and I will tell you so.

A privately underwritten plan. Bought directly from a carrier, not on the exchange. These ask health questions and can decline you, exclude a condition, or charge you more for it. In exchange, if you qualify medically, premiums and networks can be meaningfully better than what the exchange offers someone at full price.

A spouse’s employer plan. Often the cheapest route if it is available to you. Worth pricing before anything else.

A group plan of your own. If you have even one W-2 employee, small group coverage may be available. Different rules, different math.

The subsidy cliff is what catches people

The enhanced premium tax credits that ran from 2021 through 2025 expired at the end of 2025. That brought back a hard cutoff at 400 percent of the federal poverty level.

Below that line you may qualify for help with your premium. One dollar above it, you qualify for nothing.

For self-employed income this is more dangerous than it sounds. You estimate your income in advance. If you underestimate and finish the year above the line, there is no cap on how much subsidy you have to repay. A strong fourth quarter can cost you twelve months of credits in one lump sum at tax time.

Anyone whose income moves during the year should know where that line sits before open enrollment, not in April.

When a private plan is the better answer

It is worth looking at if you earn above the subsidy threshold, are in reasonably good health, work across state lines, or are paying full price on the exchange today.

It is the wrong answer if you have a significant pre-existing condition. An underwritten plan can decline you or exclude that condition. A Marketplace plan has to accept you regardless, and that protection is worth more than a lower premium.

It is also the wrong answer if you qualify for a meaningful subsidy, or if you are eligible for Medicaid or coverage through a spouse.

I will tell you which market you belong in before I quote you anything.

The tax deduction most people underuse

Self-employed health insurance premiums are generally deductible, and unlike most medical costs you do not have to itemize to claim it. The deduction has limits. It cannot exceed your net self-employment income, and it is unavailable for any month you were eligible for coverage through an employer or a spouse’s employer.

Worth raising with your CPA on your specific situation, because it changes the real cost of every option above.

What happens when you book

Fifteen minutes, phone or video, with me. Not a call center, and nobody else calls you afterward.

We will look at what you are paying now, what you would pay on the exchange with any subsidy you qualify for, and what private underwriting would look like if you are a candidate for it. You will leave with real numbers whether or not you work with me.

Every client I place gets my direct line for as long as they hold the policy. You call me, not an 800 number.