Retiring & Medicare
Written By Michael Power 6/11/2025
Key Points
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Medicare enrollment after retirement often requires extra paperwork to prove coverage and avoid penalties.
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If retiring before 65, you often can't enroll in Medicare yet and will need COBRA or marketplace coverage.
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Plan ahead well before retirement to avoid coverage gaps and headaches.
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We recommend working with a professional to determine if your employers retiree coverage is best for you compared to Medicare.
Introduction
Congratulations on making it to retirement! You have worked hard for many years and deserve to finally relax. We will help guide you through Medicare to make sure you avoid any headaches and can retire without any worries.
Comparing Retiree Options
Many people who are retiring are often given retiree coverage from their former employer. Deciding to take this coverage or Medicare is a big decision, as many retiree plans are “use it or lose it”.
We recommend talking to one of our brokers to get an apples-to-apples comparison of all your options in plain English to help you decide what path is write for you.
We promise to remain unbiased and tell you what is best for your specific health and financial needs.
How To Sign Up For Medicare After Retiring
Signing up for Medicare after 65 due to retirement is a bit different from signing up for Medicare when turning 65. You must both sign up for Medicare AND prove to Medicare that you have had “creditable coverage” to avoid penalties.
This is done by completing the Part B Enrollment form (CMS 40B) and having your employer fill out the Request for Employment Information Form (CMS-L564), which then both get sent to Social Security.
We have helped hundreds of people do this and avoid penalties and lapses in coverage in the process. We HIGHLY recommend having one of our brokers help you.
Can I Retire Midyear And Go Onto Medicare?
If you are over 65 and have creditable work coverage, in most cases you can!
Medicare offers Special Election Periods related to losing creditable work coverage. These should allow you to start Medicare Part B midyear or sign up for a Medicare secondary plan after losing your work coverage.
I Want To Retire But My Spouse Needs Coverage
Many of our clients have younger spouses who need health insurance coverage. If you are waiting for them to become Medicare eligible, you may be able to help them with a few different methods:
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Health Insurance Marketplaces
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COBRA
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Your Spouse Getting Work Insurance Of Their Own
Does Taking Medicare After 65 Limit My Options?
Starting Medicare after 65 due to retirement is very comparable to if you had taken it at 65.
Outside of a few exceptions, you should have all the same options and rights as someone turning 65.
About the Author
Michael Power is a licensed life and health insurance broker with NJ Life and Health. He has personally helped hundreds of people with their Medicare needs across several states.