Written by If self-employment promises one thing above all, it’s freedom: freedom to decide what your work is, who you work with and when and where that work takes place.
While it’s true that working for yourself offers the kind of flexibility and agency that can be hard to find in a salaried position, it does have its drawbacks. If you work for yourself, you have to have your own back, which means, among other things, paying out of pocket for the health benefits you might have previously had sponsored by an employer.
According to the Kaiser Family Foundation, nearly half of the U.S. population gets their health insurance through an employer-sponsored program. Although these policies can cost hundreds of dollars per month for a single employee, employers often pick up the bulk, or even all, of the premium cost.
Being your own boss means picking up the whole tab for your health insurance. However, if you know what you’re looking for — and are willing to get a little creative — there are ways to get quality coverage at a relatively affordable rate. Here are our best tips.
1. Explore the Health Insurance Marketplace
For most freelancers, the first place to turn — after getting on a family member’s plan, if it’s available — is the Health Insurance Marketplace. While the open enrollment period generally runs from November 1 to January 15 each year, certain life circumstances, including losing employer-sponsored health insurance, can qualify you for a special enrollment period so you can get coverage as soon as you need it.
The average cost of a silver-level plan through the Health Insurance Marketplace is around $621 per month in 2025 for a single person, which is to say, it’s no small overhead expense. However, the marketplace allows you to easily filter through plans that support your preferred providers, necessary medications, and other coverage specifics so you can narrow down your options and find the lowest-cost plan that meets your needs.
2. Consider an HDHP/HSA
Depending on the nature of your self-employment, your finances may follow an ebb-and-flow pattern, with lean months and months filled with more abundance.
Under these circumstances, a health savings account (or HSA) can be useful to have: It allows you to invest money on a pre-tax basis and withdraw it tax-free to spend on qualified health care costs, which include copayments, coinsurance and deductibles, as well as certain dental, drug and vision expenses.
Unlike a flexible savings account (FSA), which you can usually only get through an employer, an HSA doesn’t have a use-it-or-lose-it clause: The money you save in your account is yours to keep, forever.
The catch: To qualify for an HSA, you must choose a high-deductible health plan (HDHP). These plans, as their name suggests, have higher deductibles than other types of plans, with the minimum in 2025 starting at $1,650 for individuals, and you must pay all of your deductible out of pocket before the plan begins to pay. However, they also often have lower monthly premiums than similar non-HDHP plans, which can lower your total monthly overhead costs.
Additionally, contributions you make toward your HSA can lower your taxable income, which is always a bonus for freelancers who pay self-employment taxes.
3. Join a union
It may come as a surprise, but yes, there are unions for freelancers — both generally (like Freelancers Union) and for specific industries (such as the National Writers Union). While the unions themselves don’t offer health insurance, they may offer help navigating the health insurance marketplace as a service to their members — and when it comes to something as intricate and important as your health care coverage, all help is welcome.
Additionally, unions offer other benefits to their members, such as resources to help with logistics like taxes and networking or the ability to build a profile in a searchable database, which can help you find clients and connections. Some organizations, including Freelancers Union, allow freelancers to join free of charge, while others may have membership fees — sometimes on a sliding scale based on income.
4. Mull over joining a health share plan
As a freelancer, you’re already comfortable doing things differently — and there are alternative ways to approach health care coverage, too. Health share plans operate similarly to health insurance plans, but on a much smaller scale: You pay a certain monthly amount (similar to a premium) and are responsible for a certain “unshared” amount each year (similar to a deductible). However, costs may be substantially lower than traditional health care.
On the other hand, health share plans aren’t subject to the same regulations as traditional health insurance plans, which means they’re not required to cover pre-existing conditions or the same breadth of services as plans on the healthcare marketplace. Still, they present a worthwhile alternative to consider, especially for those who are no strangers to going solo.
As a freelancer or solopreneur, the added stress of paying for your own health care coverage can be just that — stressful. However, with the same enterprising attitude that got you into self-employment in the first place, you can find ways to make this important cost an affordable one.