How to Freelance and Still Get Health Insurance

How to Freelance and Still Get Health Insurance

One of the biggest fears many nine-to-fivers face is how to freelance without losing their benefits such as health insurance. You might think that it’s impossible to afford health insurance as freelancers. If you’re a millennial, you probably have a healthier perspective.

Luckily, so many of us have decided to cut our connections to cubicles that health insurance options are beginning to surface for freelancers too. Here are our Rise favorite health insurance options for freelancers.

Decent, Health Insurance For Freelancers

Decent Health Insurance

As flexible work increases in popularity, self-employed professionals demand a solution to handle benefits traditionally provided by full-time employers. In fact, health insurance is the number one concern.

Enter Decent, a company that provides affordable health plans for self-employed professionals, like freelancers, sole proprietors, and 1099 contractors, and their families. They offer year-round open enrollment to ACA-compliant bronze and silver plans available in Austin, Texas, with premiums that are up to 50 percent lower than typical market rates. Decent envisions a world where everyone has the freedom to do the work they want without sacrificing access to affordable and comprehensive healthcare. Which is why all of their plans include unlimited free primary care with a personal doctor along with access to an ever-expanding network and the world’s largest hospital system.

How to Freelance With Cobra

Health Insurance

Cobra is probably the most widely known of all the insurances on this list. You’re eligible for Cobra when you have a life-changing event, such as leaving a job. 

The good thing about Cobra is that you don’t need to pay for it until you need it (for up to 36 months after leaving your job if you live in New York). This means that you won’t need to pay for health insurance until you actually have a medical issue.

The downside of Cobra is that premiums can be extremely expensive. This is why most people only use Cobra for emergency situations and pay for routine doctor’s visits out of pocket.

How to Freelance With Oscar 


The Freelancer’s Union (an important resource for all freelancers) recommends Oscar health insurance. The union offers tons of advice on getting paid by clients on time, staying healthy and managing work-life balance.

Oscar is a less-expensive health insurance option that offers services through their own offices (and with some doctors in their network).

The downside to Oscar is that the company doesn’t have offices in every city and town. That means you’ll either need to opt-out of Oscar altogether, or travel to a city with an Oscar location for a doctor’s appointment.

How to Freelance With Health Co-Ops


Another option is a health co-op. This type of insurance has become increasingly popular with the FIRE Movement (Financially Independent Retire Early). We love this option because we know plenty of C-level executives who use co-ops, when they could easily afford to pay out of pocket for traditional insurance.

Co-ops offer an interesting alternative to traditional health insurance. They’re owned by their members, which means you’ll own a stake in your health insurance. Their premiums are relatively low and out-of-pocket costs are generally low as well.

Most plans start at $300/month for members in the 30-year-age bracket and go up to $500/month. 

Something you want to be aware of before opting for a co-op? They aren’t regulated by states or on a federal level like insurance companies are. Before signing up for it, ask around and see if anyone has negative or positive experiences with a particular co-op. 

How to Freelance With Supplemental Insurance

Health insurance, life insurance calculation concept. Top view. Modern flat design graphic elements and icons set for web banners, websites, infographics. Blue background. Creative vector illustration

If you don’t go to the doctor often (aside from routine checkups), you may want to look into supplemental insurance instead. Or, couple supplemental insurance with one of the other types of insurance on this list. It’s especially beneficial for freelancers because it can pay you benefits if you are not able to work for a certain period of time.

Supplemental insurance can cover in-patient hospital costs. There’s even supplemental insurance for cancer treatments (these plans are generally sold separately from supplemental insurance).


How to Freelance With Flat-Fee Doctors

Freelance With Flat-Fee Doctors

Finally, if none of the above ideas are in your price range, you can always just book an appointment at a flat-fee doctor. This works well for anyone who wants to keep Cobra on the backburner or who only visits the doctor for preventative care. 

Many doctors charge around $100 for a physical or a pap (most will charge patients less than an insurance company).

If you only plan on visiting the doctor a few times a year, you’re better off coupling flat-fee doctor visits with either Cobra or emergency insurance.

How to Freelance With Travel Insurance


If you’re planning on going digital nomad, you might want to simply purchase long-term travel insurance. This will ensure you stay safe in the event of an emergency while overseas. It’s also beneficial if you’re not planning on being stateside (and thus won’t need American health insurance at all).

Check out Rise for helpful career resources, tools, and more to navigate the changing world of work.

Leave a Response

More like this