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. If you’re above the age of 35, you probably think that it’s impossible to afford health insurance without a full-time job. 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 favorite health insurance options for freelancers.

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 you know has experienced particularly negative or positive service with a particular co-op. 

How to Freelance With Supplemental Insurance

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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

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 simply only visits the doctor for preventative care. 

Many doctors only 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).