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Still Working at 65: Should I Sign Up for Medicare or Wait?

Key Take Aways

Can I Keep My Employer Insurance Coverage? Can I Delay Signing Up For Medicare? Will I Get A Penalty? Is Medicare Coverage Better Than Employer Coverage?

The Core Question Isn’t Age — It’s Coverage

Medicare eligibility is based on age, but Medicare need is based on coverage. If you’re still working at 65 and have employer health insurance, the real question is:
How does my current coverage work with Medicare?
The answer depends on factors most people are never told to consider.

Employer Size Matters More Than Most People Realize

One of the biggest factors in this decision is the size of your employer. In general:
  ● Large employers often allow Medicare to be delayed
  ● Smaller employers may require Medicare to become primary
This distinction affects:
  ● Whether Medicare pays first or second
  ● Whether delaying enrollment creates future problems
  ● Whether employer coverage is enough on its own
Assuming that all employer insurance works the same way can lead to
costly mistakes.

Can I Delay Medicare Without Penalty?

In many cases, yes — but only under the right circumstances. Delaying Medicare works best when:
  ● Employer coverage is considered creditable
  ● Enrollment is handled correctly later
  ● Documentation is maintained
Penalties don’t usually come from choosing to delay — they come from delaying incorrectly.

Why Some People Enroll in Medicare While Still Working

Even with employer insurance, some people choose to enroll in
Medicare at 65.
Common reasons include:
  ● Reducing out-of-pocket costs
  ● Improving coordination of benefits
  ● Preparing for retirement ahead of time
This decision is less about rules and more about how coverage works together.

Why Others Choose to Wait

For others, delaying Medicare makes sense.
This often applies when:
  ● Employer coverage is strong
  ● Costs are predictable
  ● Medicare would not improve coverage
Waiting can be a strategic decision when it’s done intentionally.

The Risk of Doing Nothing

One of the most common mistakes is assuming:
    “If I don’t do anything, it will sort itself out.”
Unfortunately, Medicare does not work that way.
Failing to understand how employer insurance and Medicare coordinate can lead to:
  ● Gaps in coverage
  ● Unexpected bills
  ● Enrollment issues later
Choosing not to decide is still a decision.

How to Think About This Decision

Instead of asking:
     “Do I have to sign up for Medicare now?”
A better question is:
      “Does enrolling now improve or complicate my current coverage?”
That perspective leads to clearer, more confident decisions.

Q & A: Medicare and Employer Coverage

If I’m still working, do I have to sign up for Medicare at 65?

Not always. Whether you need to enroll depends on how your employer coverage coordinates with Medicare.

In many cases, yes — but the employer’s size and coverage type matter.

Penalties usually occur only when Medicare is delayed incorrectly.

Not necessarily. The goal is proper coordination, not early enrollment.

A Measured Takeaway

Still working at 65 doesn’t automatically mean you should delay Medicare — or rush into it. The right decision depends on how your current coverage works, how Medicare would integrate, and how close you are to retirement. When this decision is made with understanding, Medicare becomes a tool — not a complication.

Choosing the Right Medicare Coverage

Selecting the best Medicare coverage depends on factors like your healthcare needs, budget, and preferred providers. You can choose between:
  • Original Medicare (Parts A & B): Allows you to see any doctor or
    hospital that accepts Medicare but does not include prescription drug
    coverage (Part D) or additional benefits.
  • Medicare Advantage (Part C): Offers bundled coverage with
    potential extra benefits but may require using a network of providers.
  • Medigap (Medicare Supplement Insurance): Helps cover
    out-of-pocket costs not covered by Original Medicare, such as
    copayments and deductibles.

Key Medicare Enrollment Periods

It is crucial to enroll in Medicare at the right time to avoid penalties and ensure continuous coverage:
  • Initial Enrollment Period (IEP): A seven-month window starting
    three months before your 65th birthday month.
  • General Enrollment Period (GEP): From January 1 to March 31
    each year for those who missed their IEP.
  • Annual Election Period (AEP): From October 15 to December 7,
    allowing you to switch or enroll in Medicare Advantage and Part D
    plans.
  • Open Enrollment Period(OEP): From January 1 to March 31 for
    those who missed AEP and want to make certain changes.
  • Special Enrollment Period(SEP): Can be used anytime during the
    calendar year for those that meet certain criteria such as moving to a
    new service area.

Finding Help with Medicare

Understanding Medicare can be complex, but you don’t have to do it alone. Licensed Insurance Brokers, Medicare.gov, and state health assistance programs can provide guidance tailored to your specific needs.
By taking the time to explore your Medicare options, you can make informed decisions that ensure you receive the healthcare coverage that best suits your lifestyle and budget.
Do I have to sign up for Medicare?
It depends upon your current coverage. If you are employed and your employer has over 20 employees then you can delay signing up for Medicare and avoid penalties.
No, You will have to enroll in a stand alone Part D plan or a Medicare Advantage Plan(Part C) to get coverage.
There are no networks with Medicare and most doctors and hospitals accept it. However, Medicare does not cover 100% of services so a Medicare Supplement or Medicare Advantage plans is advisable.

Mike Miligi- Owner

For over 10 years, Mike has been assisting Seniors and other Medicare-eligible individuals in understanding the ins and outs of Medicare and Medicare Health Insurance options, including Medicare Advantage Plans(Part C), Medicare Supplement Plans(Medigap), Prescription Drug Plans(PartD), and Dental and Vision programs.
Mike is Licensed in seven States and Certified with 11 Insurance Carriers. He has helped thousands of individuals decide on the best course of action for their particular Health Insurance needs. Because Mike is an Independent Medicare Health Insurance Broker, he works for the client, not the Insurance Carriers, and is able to provide his clients with accurate and unbiased Health Insurance options.
Mike recertifies with CMS(The Centers for Medicare and Medicaid Services) annually, regularly completes Continuing Education Courses required by individual State Insurance Departments, and keeps abreast of industry trends and standards to offer his clients the most up-to-date information.
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