Still Working? Start Here.

Many individuals delay Medicare because they are still employed.

That can be appropriate — or costly — depending on your situation.

Whether to enroll in Medicare while still working depends on several factors — primarily the size of your employer and the quality of your current coverage. In some situations, delaying Medicare enrollment is completely appropriate and penalty-free. In others, it can result in gaps in coverage, unexpected costs, and enrollment penalties that follow you for life.

The most important variable is how many employees your company has. If your employer has 20 or more employees, your employer plan is typically considered primary and Medicare is secondary — meaning you may be able to delay Medicare Part B without penalty. If your employer has fewer than 20 employees, Medicare becomes primary, and not enrolling could leave you with significant coverage gaps.

Risk Exposure

Common risks include:

Unexpected penalties

Gaps in prescription coverage

Employer plans that do not coordinate well

Delayed enrollment misunderstandings

The rules vary depending on employer size.

Grandfather teaching his grandson to fish along a river — the family security that depends on getting Medicare timing right

Transition Timing

Important questions:

How many employees does your company have?

Is your prescription coverage creditable?

When does your employer coverage end?

What costs are you exposed to with your employer coverage?

Small details matter here.

Family running joyfully through a meadow at golden hour — confident transition from employer coverage to Medicare

Get Clarity Before You Decide

This is one of the most common areas where guidance prevents costly mistakes.

Our Role as Your Advocate

At The Advocate Group, our role is not to push one plan over another.

We take time to understand your situation, explain your options clearly, and help you compare plans so you can make a confident, informed decision.

The Advocate Group full team — guiding employer-to-Medicare transitions in Springfield, Missouri

Frequently Asked Questions

Should I enroll in Medicare if I still have employer insurance?

It depends on your employer’s size. If your employer has 20 or more employees, you can typically delay Medicare Part B without penalty while on employer coverage. If your employer has fewer than 20 employees, Medicare becomes primary at 65 and you should enroll to avoid coverage gaps.

What happens if I delay Medicare and my employer coverage ends?

When employer coverage ends, you have an 8-month Special Enrollment Period to sign up for Medicare Part B without a late penalty. It is important to enroll during this window — not just when you lose coverage.

Can I have both Medicare and employer insurance at the same time?

Yes. Many people have both, and coordination of benefits rules determine which pays first. Whether that arrangement works well depends on your employer’s plan structure and group size.

Will I be penalized for delaying Medicare enrollment?

A penalty may apply if you delay Medicare Part B or Part D without qualifying coverage. The Part B penalty is 10% per 12-month period of delay and is permanent.

Our Values

At The Advocate Group, everything we do is built on three core principles.

Integrity

Education

Trust

We recommend what is best for you — not what pays the most. Transparency is non-negotiable.

An informed client is an empowered client. We make sure you understand your options so you can make confident decisions.

Healthcare and financial protection require vulnerability. We earn trust by showing up consistently, honestly, and reliably.

the Advocate Group experience

What Our Clients Say

- janet m.

"Jason Avery has been such a great person to provide us information for our best Medicare plan. He takes the time to thoroughly review circumstances to advocate for his clients. He even came to our home to meet with us. Very thankful for his assistance!"

- clean s.

"Jason and his team are in the business of creating peace and calm. With SO many options in the healthcare industry, it’s overwhelming and difficult to navigate successfully. Jason guides his clients with confidence and genuine interest in their wellbeing."

- barbara w.

"Jason Avery is one of the best Medicare advisors! He directed me to products and services that were best suited to me and compared them to my current choices I had already made. I took his advice and I ended up having a good year of health & prescription provider care."