Health Insurance When You Aren’t Covered By An Employer or Medicare

Money Magazine had an interesting article this month about a man who is financially ready to retire at 56 but is not sure how he will handle medical coverage until Medicare kicks in at 65.  This article jumped out at me because even as a very healthy, normal weight, self employed, 30 year old, I have had trouble getting coverage.

The article suggests the following:

1) Get in shape. Aim for optimal heath at least a year before you apply for insurance.  This will help you qualify for insurance and better rates. 

2) When you schedule your annual checkup, ask your doctor to review your medical history with you for accuracy.  If you have applied for individual life, health, disability or long-term-care insurance within the past seven years, the industry may already have a file on you.  You can get a copy of it from

3) Shop for individual health insurance months before you leave your job. is a good place to start as well as

4) Evaluate how your private health insurance option measures up against COBRA.  Through COBRA you can stay on your previous employer’s insurance plan for 18 months, but it isn’t cheap.

5) Ask for an estimate of your premiums and assume these will grow at 10% annually as they have recently.  Add up what you will pay until you turn 65.  This unfortunately may dim many people’s chances at early retirement.

5) If you cannot get individual coverage after COBRA you will be HIPAA-eligible, guaranteeing certain backup coverage.  States make available last resort insurance if you are HIPAA eligible.  Be wary, these plans are very costly.

6) Some states (NJ, NY, VT, MA, ME) mandate guranteed group plans for businesses with even one employee, which may make sense if you plan to do any type of freelance work.  Go to  Even if you are not in these states you may be able to get insurance through your local chamber of commerce.

Whatever approach you take, please, please, please take this seriously as it is quite difficult to get insurance once you are on your own!  Take it from someone with experience!

Please contact Dollars & Sense Education to bring our seminars to your company or organization!

Dollars & Sense Education – Raising Your Financial IQ!


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