Health Insurance for Freelancers: 17 Smart Options + Creative Solutions

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Health Insurance for Freelancers: You've Got Options.

Health Insurance for Freelancers: You've Got Options. Makealivingwriting.comTrying to figure out health insurance for freelancers? Enrollment time for many plans is right now. The choices can be confusing—and expensive.

But decent health insurance for freelancers doesn’t have to be a pipe dream. With the explosion of the gig economy, promising and creative alternatives are emerging.

Some options bypass the insurance system completely. Or if you choose traditional insurance, there are several ways to lower your costs. Planning to quit your full-time job? Short-term options exist to get you over the healthcare hump.

Even if your health coverage is working well for you, now is a perfect time to re-evaluate and make sure you’re still getting the best value.

If you’ve been going without any health coverage, take advantage of this open enrollment period to research health insurance for freelancers.

You have until December 15, 2019, to pick your plan. Health insurance for freelancers comes in all shapes and sizes, so it’s important to choose the plan that meets your needs and your budget. Choose, but choose wisely.

Need help picking the right plan? Check out this list of 17 health insurance options for freelancers, plus some creative solutions.

1. Affordable Care Act

Passed in 2010, the Patient Protection and Affordable Care Act (nicknamed Obamacare) offers affordable insurance for many low-income U.S. residents. Enrollment is open through December 15, 2019. If you don’t qualify for subsidized care under the ACA, you can still use the site to gather information and compare different plan types. Log in early and bring an extra dose of patience with you, since the site sometimes bogs down.

Be sure you’re accessing the actual government website through the link above. Many fake sites have popped up.

2. Spouse or partner’s policy

Your partner’s insurance might offer better, cheaper coverage than you could find on your own. Or it might not. Check out other alternatives too, and update your research every year to make sure you’re still getting the best value.


Ditching your day job? You can take your healthcare coverage with you for up to 18 months. You’ll have to make the payments yourself, but COBRA (Consolidated Omnibus Budget Reconciliation Act) gives you time to find your freelance feet and explore other healthcare choices.

4. Groups, organizations, and associations

Check out the Chambers of Commerce and professional associations in your area. Some of these organizations offer group health insurance plans. If there are costs to join the groups, factor those in to your total healthcare budget. Be aware that association-based health insurance is in flux, and some groups like the American Society of Journalists and Authors have chosen to steer clear of it for now. Do your research.

5. Freelancer’s Union

New York residents can choose several levels of health care plans through the Freelancer’s Union. If you live elsewhere, you’ll find links and information on their website to connect you with health insurance for freelancers available in your area.

6. Short-term health insurance

Short-term policies are usually cheaper than traditional comprehensive insurance. You can purchase them at any time, without waiting for an enrollment period. A short-term policy can be a perfect stopgap while you’re waiting for open enrollment or figuring out your next steps. Be sure to get a policy that includes the coverage you need most. They vary greatly.

7. Health indemnity plans

Tired of paying for more insurance than you ever use? If you’re in good health without pre-existing conditions, a health indemnity plan might save you money. You pay a set amount for coverage. If your costs are less than that amount, you get the extra back. If your costs are more, you pay the difference.

8. High-deductible insurance

High deductibles are another way to reduce costs if you and your savings account are both healthy. You’ll pay routine medical expenses yourself, and the insurance will kick in if your bills go above a certain amount. Brace yourself—deductibles on some policies can shoot as high as $10,000 or $20,000. But if you’re at low risk for health problems, buying insurance this way just might save you a ton of cash.

9. Health savings accounts

Tax-sheltered HSA’s go hand-in-hand with high-deductible plans. You can take the money you’re saving on insurance and put it in an account dedicated for healthcare spending. You get a tax credit for the amount that’s in the HSA, and you’ll have funds ready for those routine medical expenses that your high-deductible plan doesn’t cover. Be sure to choose a high-deductible plan that allows you to use an HSA. Not all of them have this option.

10. Business or group policies

If you’re registered as a business, look into buying group or corporate health insurance through the business. This option can sometimes get you better coverage for less money than an individual plan. The federal Small Business Health Options Program is a great place to start your research.

Each state has different rules about who qualifies for business insurance. In many places, you’ll need to have at least one employee besides yourself. Your state may have additional business insurance options that aren’t available nationally. Contact state small business development programs to see what’s offered in your area.


Founded in 2012, OSCAR describes itself as “a health insurance company centered around the patient.” It takes advantage of digital technology to help members manage their care, take charge of their health, and find providers. OSCAR offers several individual and small-business plans. It’s available in nine states, including New York, California, and Texas.

12. Healthcare credit cards

Companies like CareCredit offer credit cards just for medical expenses. You can spread out payments over several months with no interest. Be careful. Interest fees do kick in eventually, so only use this option if you’re sure you can pay off the balance quickly.

Creative health-insurance options for freelancers

Maybe you’re not satisfied with your options, or you’re looking for a way to save more on healthcare. Check out these creative solutions:

13. Medical-cost sharing ministries

If you’re a Christian, these faith-based plans offer a lower-cost alternative to insurance. Everyone makes monthly payments into a pool, and the money funds the health care costs of members in need. Most plans have restrictions on who can participate. You may need to sign a statement of faith, avoid risky behaviors like smoking, or be free of pre-existing conditions. There’s also no guarantee your bills will be paid. But if you meet the criteria, it’s an option worth looking into.

14. Crowdfunding

If the worst happens and your family is hit with staggering medical bills, consider setting up an online fund. GoFundMe is the leader in this field, and Facebook also allows personal fundraising. Please don’t rely on crowdfunding as your only way to pay for healthcare, but if you need it, use it.

15. Medical tourism

Traveling outside the U.S. for health care is on the rise. If you need a non-urgent procedure and you’re feeling adventurous, medical tourism might be the ticket you’re looking for. Many high-quality providers and facilities are available abroad, but check them out thoroughly before you commit.

16. Cash-pay discounts

If you can pay cash in full at the time you receive services, your doctor or hospital might reward you with a generous discount. They may not volunteer this on their own, so always ask. New York City residents can negotiate cash-pay care through Slingshot Health, a new service that acts as a broker between providers and patients. Expect more insurance-bypass options like Slingshot to surface in the future.

17. Direct primary care

Are you frustrated by short doctor visits, long waits, and insurance bureaucracies? With a direct primary care model, you get unlimited access to a doctor or other health provider for a flat monthly fee, usually under $100. Some providers do lab work and fill basic prescriptions on site, at lower costs than you’d pay elsewhere.

If you have kids, you may be able to add them to your membership for a very small additional charge. Combine direct primary care with a hospital or high-deductible policy to make sure you’re covered for major health issues, too.

Be a healthy & happy freelance writer

This list is just a starting place. Do your own research and see what’s available where you live. Or combine a few different ideas from this post to come up with the best plan for you and your family. A few more healthcare tips for freelance writers:

  • Don’t overlook local insurance brokers. A good one will be familiar with a variety of plans and can steer you toward the best fit. Consult with more than one for a balanced perspective.
  • Move up and earn more. For most U.S. freelancers, health insurance will take an enormous bite out of your budget. There’s no way to avoid this reality, and it isn’t likely to change. That’s why it’s important to keep raising your rates, exceeding your freelance income goals, and building your savings so you can afford the coverage you need.
  • Take excellent care of yourself. Choose the insurance and health coverage options you need to protect yourself and your family, but also be proactive about staying as physically and mentally healthy as you can.

Your health and your ability to work is your most important asset as a freelance writer. Guard it well.

What’s your plan for health insurance as a freelancer? Share your tips in the comments below.

Maria Veres is a freelance writer based in Oklahoma City and a frequent contributor to Make a Living Writing.

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10 comments on “Health Insurance for Freelancers: 17 Smart Options + Creative Solutions

  1. Zoe Campos on

    Thanks for explaining that health care insurance plans for freelancers come in all sorts of shapes and sizes. I don’t want to be employed in a huge company and pursue freelance instead, so this article will definitely be useful for me. Maybe I’ll finalize my career plans first before shopping around for individual health care plans.

  2. Scott Reaver on

    Good post. I would recommend having medical coverage as part of your auto insurance. It ONLY covers car accidents but — given the low cost — it could be part of your overall healthcare-funding strategy

    • Carol Tice on

      I don’t really think so, Scott — I mean, you should have medical coverage with your auto policy for medical expenses related to any accident. But that’s all it would ever cover…still need help with everything else healthcare in another way.


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