Most retirees will get their health insurance through Medicare. They may purchase a Medicare Advantage Plan, or they may have Original Medicare with a Supplement.

But one way or the other, most Baby Boomer retirees will be on Medicare.

Everyone knows you become eligible for Medicare when you are 65.

But what happens when you retire BEFORE you reach age 65?

Or, what happens if you have health insurance from your spouse’s group plan, and your spouse retires and you lose that coverage?

This is a serious issue!

If you don’t have health insurance coverage you could have a huge healthcare bill completely derail your retirement plans. All that effort you put into saving into your 401(k) and IRA for all those years (decades!) could be completely undone.

So how do you prevent this from happening? By getting retirement health insurance before Medicare eligibility. In other words, before age 65.

Here are 4 options that may be available to you. Some options will be better than others depending on your specific situation. So be sure to check them all out to know which will work out best for you.

  1. COBRA – You could always consider COBRA. If you are covered under your spouse’s plan and he/she retires before you are 65, you may qualify for COBRA coverage. This coverage will typically last 18 months. It will probably be more expensive than normal because the employer will no longer be subsidizing a portion of your premiums.
  2. Employer Plans – Your former employer (or spouse’s former employer) may provide retiree health insurance benefits BEFORE you reach age 65. Not many employers do this. But why not check it out to see if it’s available. It may be more affordable than COBRA. AND it may last longer than 18 months, even up until you are 65.
  3. Part-Time Work – You could work part-time for an employer that provides health insurance coverage for part-timers. Some companies are willing to do this because they see an opportunity: They see older, experienced workers that would make good employees, and that are only interested in working part-time because they are ready to slow down a bit from the rat race. If you like the idea of continuing to work part-time in retirement, this may be a good option for you.
  4. Obamacare – You could purchase individual health insurance under the new Obamacare laws. If you have pre-existing conditions, don’t worry because insurance companies won’t ask you about your health. Keep in mind, as with many of these options I’ve mentioned, you need to act within a certain time frame. Typically you have 60 days from losing your group health insurance to apply for an Obamacare compliant insurance policy. If you miss the window you will have to wait until the Open Enrollment period begins on Nov. 15th.

With all these strategies keep in mind the issue of price, as well as the coverage you are getting. Some strategies may make more sense than others for your particular situation.


Hope that helps. And if you know anyone else that is retiring soon that is not yet 65, make sure you forward this article and video to them. You can quickly do this for your friends by clicking on the Facebook icon on the left of the screen.

And you have something you’d like to ask me over the phone, then you can schedule a 20 minute phone call with me by claiming a spot on my calendar. Just CLICK HERE to do so.


Chris Hammond