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Working Past 65 & Medicare

Which is better: Should I stay on my employer coverage, or should I switch to Medicare?

Gain the confidence and clarity you need with your working past 65 & Medicare checklist or speak to a local advisor today.


Employer vs. Medicare

Now more than ever, people are working past 65 to pursue career goals, save for retirement, or reach full Social Security benefits. If you’re age 65 or older, you can sign up for Medicare, regardless of your current employment status. Just remember, retirement is NOT a requirement for Medicare ― and all its benefits, some that you can’t get with employer plans. In addition, your cost may be much lower than your employer coverage. Learn more about Medicare when turning 65.

Below, we explore some of the key factors to consider when working past 65 and considering Medicare, including comparing coverage and benefits, how and when to sign up, and what to do if you're unsure of your options.

Medicare Benefits

Many people think that Medicare is only for retirees, but this isn’t true! You can enroll in Medicare while continuing your career and adding to your retirement savings. Your working status does not impact your eligibility for Medicare. If you sign up for Medicare while you’re still working, it may make your eventual retirement that much smoother because you won’t have to change your health insurance when the time comes.

As you compare your employer coverage to Medicare, here are a few factors to keep in mind.

Medicare often is less expensive.

When you weigh your Medicare options, you need to consider: What is my premium? What is my deductible? What is my maximum out-of-pocket? Do I have a spouse or any dependents on my coverage?

If you have a high-premium or high-deductible plan through your employer (or your spouse’s employer), switching to Medicare may be more cost-effective. Many Medicare plans offer first dollar coverage, meaning you can pay little or nothing out of pocket for health care visits.

Know what steps to take and when with our checklist.

Medicare often provides more benefits.

Compared to your employer group health insurance that offers few options, Medicare isn’t one-size-fits-all. You can choose a plan based on your needs and budget, rather than your employer’s. Plus, many Medicare plans are offered by the same insurance carriers that provide employer coverage. If you enjoy the customer service you get from your current insurance carrier, you may be able to continue with them on Medicare.

A Medicare plan could give you more:

  • Gain well-rounded coverage
  • Keep your costs low
  • See if you qualify for additional benefits
  • Get lifelong support for your plan-related needs, billing or claim issues, and more!

You can enjoy these benefits while continuing your career when you enroll in Medicare without retiring.

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How & When to Sign Up

Do I need to sign up for Medicare at 65?

If are turning 65 and work at an organization with fewer than 20 employees, you’ll be required to enroll in Medicare once you become eligible at age 65. However, if you work for a larger organization, you can choose between Medicare and your employer’s group health insurance. Either way, you can have the option to enroll in Medicare without retiring.

When am I eligible to sign up for Medicare?

If you find yourself in this window of time, you are officially eligible.

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Initial enrollment period
begins three months before
the month you turn 65

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Your 65th Birthday

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Initial enrollment period
ends three months after
the month you turn 65

Expert Tip* Enrollment requirements and deadlines can get tricky, so even if you’re unsure about starting Medicare during this timeframe, contact our team now to make sure you’re meeting deadlines and avoiding coverage gaps or potential penalties and fees.


If you’re in your initial enrollment period or already past age 65, you can sign up for Medicare regardless of your current employment status. We make it easy to enroll in Medicare without retiring. Our team supports you through every step in the Medicare process—from finding the right plan to enrollment and beyond. We'll handle all the paperwork and make sure you’re on track for a smooth transition to Medicare. Plus, our services are provided at no cost or obligation.

Avoiding Late Enrollment Penalties

Late enrollment penalties (LEP) are issued to individuals if there’s a lapse in their health care coverage once they are eligible for Medicare. The penalty amount depends on how long the person has gone without creditable coverage. This is added to their Medicare monthly premium for the duration of their Medicare plan enrollment. There are three types of LEPs:

  • A Medicare Part A LEP for going without creditable hospital coverage (for those who don’t automatically qualify).
  • A Medicare Part B LEP for going without creditable medical coverage.
  • A Medicare Part D LEP for going without creditable prescription drug coverage (the most common LEP).

Creditable coverage is any health care coverage that is comparable to or better than what is available through Medicare for prescription and/or medical coverage. 

Medicare vs. COBRA

The Consolidated Omnibus Budget Reconciliation Act (COBRA) allows individuals who are no longer employed to maintain employer-provided health coverage for 18 – 36 months. However, enrolling in COBRA can be rather expensive as those who utilize COBRA as their health care plan may be required to pay up to the employer’s full cost, plus an additional two percent. While the general guidelines surrounding COBRA eligibility seem straightforward, there are additional rules and exceptions for individuals who are 65 and older and find themselves without a job but are not yet retired. Read more.


Not sure what to do?

You’re not alone. Medicare can seem overwhelming. You’re likely being bombarded with mail and commercials about Medicare that are confusing. Don’t worry; help is here!

We recommend you start with a conversation with one of our local advisors. Our team will take the time to get to know you one-on-one and hear what matters most to you. We’ll discuss your unique needs, plans for retirement or for working past 65, and other factors that will determine your specific next steps as they relate to Medicare and the enrollment process.

Gain the clarity you need.

Deciding when to enroll in Medicare is a big decision. That’s why you need a local partner like RetireMed as your guide. We’re passionate about helping people just like you! We’ll answer any questions you may have about penalties, HSAs, spousal coverage, employer coverage compared to Medicare, costs, and more. We view our clients as our partners, and we will give you the tools and resources you need to make a confident decision for your health care plan―all at no cost or obligation to enroll.

Our experts in Medicare will:

  • Get to know your individual needs
  • Research custom coverage options
  • Help you compare plans
  • Help you enroll in the right plan
  • Provide lifelong support

Meeting with us is easy:

  • In-person at our Miamisburg or Blue Ash office
  • Phone appointment
  • Zoom video appointment

We’ve helped more than 50,000 people just like you in Ohio, Kentucky, Indiana, and Florida.