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A Guide to Health Insurance for Freelancers

As a freelance journalist, sometimes security can feel untouchable. Fortunately, when I first entered the industry, I was able to stay on my family’s health insurance. When I had to make the move off, at age 26, I found myself googling home remedies for various ailments. I simply didn’t think I’d be able to afford insurance on my own. 

But after some consideration, I knew I had to make it work. Thus, my search for the best and most cost-effective health insurance as a freelancer, began. 

In 2020, around 157 million people received employee-sponsored insurance. But the number of freelance workers has been on the rise in the US. From 2019, to 2020, the amount of gig workers in the US increased by 8 percent. Now, freelancers comprise 36 percent of the workforce. And to make matters more interesting, 58% of people who switched to remote work during the pandemic are considering making the switch to freelance. 

However, finding an independent health plan can be really complicated and confusing. With the help of a rep from the LGBTQ Center, a spot that offers support to LGBTQ+ population in Manhattan, I found a  New York-based independent health plan. Hence, I’ve overcome all the hurdles so you don’t have to. 

Here’s what to do if you’re a freelancer, or gig worker, and need health insurance in a pinch. 


What to know about timing

While searching for health insurance as a gig worker, there are a few important dates to keep in mind.

Currently, yearly open enrollment — the time period in which you can purchase a healthcare plan with or without a qualifying reason — is from November 1st to January 15th. (Check on your state’s enrollment period, because some states, like California, New Jersey and New York, have an extended enrollment period.)

However, say you quit your 9-5 in June, and still, of course, want to find insurance. Don’t worry; You still can enroll in a plan after open enrollment closes. There are just some specific ways to qualify. 

Following open enrollment, health insurance is still available under “special enrollment plans,” These require proof of extenuating circumstances, which can include pregnancy, having or adopting a child or getting married. These also include losing coverage, from leaving a job, or moving. 

If you’re looking to make the shift from a full-time job to the gig economy, you’d be revoking your employee-sponsored health plan. However, you’ll still be able to qualify for a special enrollment period; 60 days following the loss of your coverage, you can still enroll in a health insurance plan. And you can enroll in Medicaid at any time. 

There are also some pandemic exceptions; In certain circumstances you can still enroll if you lost coverage more than sixty days ago. (Check out the government’s healthcare site for more info.)

An alternative option for loss of coverage is opting into the the Consolidated Omnibus Budget Reconciliation Act (COBRA), which is a federal law that allows workers who have lost employee-sponsored health insurance coverage to continue to pay into that same insurance company for a period of time (usually 18 months post-employment, but it varies case to case).

The benefit of utilizing COBRA is you won’t have to switch doctors or specialists who may not accept a new insurance plan. However, paying for coverage will cost much more than it did when you were an employee. If you elect to move forward with COBRA, once your designated time period comes to an end, you’ll get looped into the same special enrollment period mentioned above. 

Your options

Insurance plans land in three categories: bronze, silver, gold, and platinum. Of the three different plans, bronze plans tend to have high deductibles with lower monthly costs. Each plan adjusts accordingly from there. For instance, gold and platinum policies require more out-of-pocket each month, but cover costs much quicker. 

The Freelancers Union notes that silver plans are the most popular choice for their members. Healthcare consultant Sarah Gravelin says that’s likely because silver plans are the “middle of the road,” in terms of cost and deductibles. Medicaid is also a popular choice for freelancers because it’s free, but it’s only available to those who fall under a certain income bracket, which varies state-to-state.

In general, what works for a freelancer who makes $100,000 a year may not work for a freelancer who makes $40,000. You can typically find the best plan for you by comparing plans on a healthcare marketplace. (Read more on that below.) 

Aside from costs, you should definitely consider your medical needs before making any commitments to a new plan. For instance, if you have prescription drug needs, you’ll want to check with the insurance provider’s copayment policy. Some plans might only kick in at “in-network pharmacies” — meaning they’d cover costs at CVS, but perhaps not your local mom and pop. 

If you have a chronic illness, or have to take frequent visits to a specialist, choosing a plan with a lower deductible might be the better choice, so that the insurance company can start covering costs more quickly. 

Most health plans do not include dental and vision components. You’ll likely want to purchase these separately. Either way, vision and dental costs tend to be significantly less than medical plans (some vision plans are as low as $13/month, while some dental plans start at $25). 

Freelancers — especially writers and photographers —  spend a lot of time looking at a screen, making visual health crucial. On the other hand, doctors and dentists agree that there’s a strong link between oral and physical health, so dental insurance should be a strong consideration no matter your field. 

Where to look

For each state, where to look and where to enroll varies. Nationwide, healthcare.gov or the Obamacare site can provide options or make it easy to schedule a call with an insurance advisor who can walk you through the process. 

However, many states recently began operating their own health insurance marketplaces in an effort to make the process easier. So if you live in California, Colorado, Connecticut, District of Columbia, Idaho, Kentucky, Maine, Maryland, Massachusetts, Minnesota, Nevada, New Jersey, New Mexico, New York, Pennsylvania, Rhode Island, Vermont, or Washington, you should enroll on your state’s marketplace website. 

This also helps centralize plan options specific to your state or city. For instance, MetroPlus Health serves only those living in New York City’s boroughs, while coverage from a provider like Blue Cross Blue Shield is available in all 50 states. 

To avoid any scams, Gravelin recommends going through your state’s marketplace or healthcare.gov in order to ensure a plan is compliant with the Affordable Care Act (ACA) and therefore government regulated. “We’ve been seeing a lot of ‘associations’ saying that they’re for self-employed people, but it’s a big gray area,” Gravelin says. “These companies aren’t regulated and a lot of them have gone under, leaving their customers with thousands of dollars in unsettled claims.”

Gravelin says these companies typically reach out directly freelance workers, or appear in online searches of “the best insurance plans for freelancers.” Stay cautious and always double check through healthcare.gov or your state’s marketplace to make sure the insurance company is verified.

Beyond that, any ACA-accredited plan will have a metal in its plan’s names (silver, bronze, gold, etc.). 

In New York, the Freelancers Union, an advocacy group, is free to join. Its website also makes it easy to search for a healthcare plan. However, it doesn’t include every insurance company available, only ones that are partners of the org. 

If you’re working in an industry where you’re exposed to physical risk, you might want to invest in an additional disability plan as a safety cushion for any unforeseeable incidents that happen on the job. Many of these plans are short-term. You can find a options at Life Preserve, State Farm or Policygenius.


Many sectors of the gig economy can feel isolating, especially during a pandemic. Whether you’re working from home, or spending most of the day alone in a delivery vehicle, you might be lacking some of the benefits of other types of work. 

Hopefully with these tips, you can find a health plan that works for you. 

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The Paper Gown, a Zocdoc-powered blog, strives to tell stories that help patients feel informed, empowered and understood. Views and opinions expressed on The Paper Gown do not necessarily reflect those of Zocdoc, Inc. Learn more.