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Advice / Succeeding at Work / Break Room

Know Your Options: Finding Individual Health Insurance

It’s easy to take a great health insurance plan for granted, especially if it’s always been provided by your parents or your employer. But, if you find yourself joining a startup that doesn’t offer benefits, working for yourself as a freelancer or entrepreneur, or taking time between jobs, you might wind up having to look for coverage on your own.

And anyone who’s been in that boat knows that finding good health insurance (for a good price) is definitely not easy. So, before you dive into the sea of plans and premiums, here’s an overview of the options you’ll be faced with, and what you need to know about each one.

The Basics

To get started (and to keep yourself from getting overwhelmed), check out sites like eHealthInsurance and InsureMonkey, which outline the factors you should consider and give you a rough estimate of what different plans will cost. Also spend some time clicking around the InsureMonkey University for a more thorough run-down of health insurance basics.

Family, Group, or Student Rates

If you’re able to get on a group plan, it’s often a cheaper option than plans you can find on your own. If you’re under 26, you can get continued coverage from your parents’ health insurance, thanks to the Affordable Care Act. Or, if you’re in school, look into university-sponsored plans—many offer discounted group insurance or on-campus health care. Independent contractors can also look for group rates through industry organizations or trade groups.

Short-Term Plans

Short-term plans, which usually max out at about six months, are best if you’re waiting for your new employer’s benefits to kick in, or if you’re fresh out of school and expecting to find a job with benefits fairly quickly. These plans rarely cover preventative health care (like flu shots) but they offer you protection (and peace of mind) if you’re faced with an unexpected hospitalization or illness.

They’re highly customizable in terms of rates and length of commitment, and are usually the cheapest individual plan option. You can find a short-term plan by going to collective quote sites like eHealthInsurance or directly from healthcare providers like United Health One or Assurant Health.

Long-Term Plans

Long-term health insurance coverage closely resembles the plans you get through most major employers. You’ll have similar choices and considerations—like high deductible vs. low or  HMO vs. PPO plans—and a range of pricing based on your health history and location. If you have a pre-existing medical condition (which can even mean things like migraine headaches), you probably won’t qualify for short-term coverage, so a long-term plan with a high deductible will be your primary option.

If this is the route you're considering, it's best to compare plans on eHealthInsurance, consult with a health insurance agent (who works for one company), or work with a health insurance broker (who represents multiple companies, like a real estate agent). A quick search in your area will help you find a local representative who will help you assess your needs and present you with cost-effective options.


If you were recently laid off, quit, had your hours reduced, or divorced a spouse from whom you received coverage, check out the government-mandated COBRA program. In general, your former employer is required to cover you on its group plan for up to 18 months (or 36 months in the case of divorce, legal separation, or your spouse’s death). Caveats: if your company has less than 20 employees, it’s doesn’t have to offer COBRA, and if you were let go for “gross misconduct,” you won’t qualify.

But if COBRA’s available to you, it’s usually a good option—it will cost more than you were paying for health insurance when you were employed, but you’ll get the same level of coverage (which is often better than you could afford on an individual plan). You should receive information on signing up for COBRA from your employer, either before you leave or in the mail shortly thereafter. If not, reach out to your former HR department and ask.

Dental & Vision Plans

Don’t forget about vision and dental insurance—they aren’t always covered by group plans, and they’re hard to come by through short-term policies. You can check out your options for dental coverage through sites like, investigate individual eye care plans through major providers like VSP, or pursue savings on combined dental and vision coverage plans available from companies such as Humana One.


Other Resources

After you’ve settled on a plan, make sure you’re prepared for all of your health expenses—rates, deductibles, office visits, prescriptions, and any out-of-pocket expenses not covered by your plan. Try sites like Simplee, a free online service to help you organize and chart your medical expenses, or DestinationRX, a search engine that helps you find the best price for your prescriptions.

Finding health care on your own isn’t easy, but you do have options. If possible, do the groundwork far in advance—for example, if you’re planning to strike out on your own and freelance—as some plans take up a few weeks to decide whether you qualify. Do your research before signing any dotted lines, and take the time to make sure the plan you choose is the best one for you, your health, and your situation.

Want more? For more tips and information on decoding your health insurance options, check out our guide to picking the best benefits package for you.

Photo courtesy of David Wall.