How To Get Health Insurance When You’re Self-Employed

Cropped SingleCare logo By | January 22, 2016

Getting healthcare when you’re self-employed can be a job in itself. So how can you find the best option?

Freelancing for a living or working for yourself can be not only rewarding but also risky business. You get to pursue your passions on your own terms, whether that’s blogging, digital design, journalism or any other enterprise. But when you work outside of big corporate constructs, you often give up the chance to be part of a large, partially or fully subsidized healthcare plan.

According to, you’re considered self-employed if “you have a business that takes in income but doesn’t have any employees.” Entering this so-called “Freelance Nation” can be an exciting— and daunting—task. It’s important to ensure that you’re ready to strike out on your own, especially if you’re transitioning from the stability of a role at a larger organization with benefits.


Lay the Groundwork

First things first: stock up on essentials. This means you should be able to cover your bills, food expenses, and rent/mortgage for as long as possible before quitting a job, and — if feasible — your savings should be piled up in anticipation of business expenses, potential stretches of low income, and emergency costs. Having a buck to spare will help you transition into self-employment and relieve some stress while you pursue your dream career.

Moreover, that extra security blanket will help you pay the costs of healthcare — and a monthly health insurance premium, should you choose enroll in an independent insurance plan.

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Know Your Healthcare Options

If you’re looking for insurance, you have a few choices. You may buy a plan directly through the Federal Health Insurance Marketplace on during an Open Enrollment Period.

A common choice for a reasonably healthy self-employed person is an Health Savings Account qualified, high-deductible plan, which requires you to pay a higher deductible before your insurance kicks in, but offers lower monthly premiums. This provides an affordable option for those who do not require frequent care, but want coverage in case of emergencies.

For lower-income individuals with children, enrolling in Medicaid and the Children’s Health Insurance Program are good options for obtaining low-cost insurance plans that cover essential services for both adults and children. Enrollment qualifications vary by state, and you can see if you are eligible on

Alternatively, if you have a spouse with insurance through an employer, you may be able to extend their insurance to a family coverage plan. Although the monthly costs will be higher, an individual policy could be even more pricey. In this case, you would be disqualified from obtaining savings, such as premium tax credits, as from a Marketplace plan.

If you were previously insured through work or insured under a spouse’s employer, you may also be covered for a period under the Consolidated Omnibus Reconciliation Act (COBRA), which requires an employer to continue group coverage to an employee and their dependents in certain cases, such as a divorce or the termination of said employee.

If you already have COBRA coverage and you wish to switch to a Marketplace plan, you may do so, as long as you are within an Open Enrollment Period or qualify for a Special Enrollment Period. You can learn more about enrollment periods at

Finally, if none of these options are suitable, you may try joining a professional, special interest or trade group to gain coverage. For example, the National Association for the Self-Employed offers insurance policies, and unions such as The Freelancers Union provide comprehensive plans at startlingly low premiums.

Fill in the Gaps with SingleCare

If you find it far too difficult to relinquish your hard-earned wages to a monthly fee, you’re not alone. Programs like SingleCare offer members the opportunity to pay for only the services needed, at prices of up to 60% lower than what they would have paid out-of-pocket — no deductibles, monthly premiums, or membership fees required. This pay-as-you-go policy also means that a SingleCare membership can fill any holes in existing coverage, so you’ll be ready to take the booming gig economy by storm.

(Main image credit: kaspiic/Thinkstock)