Should I Take Medicare at 65 If I'm Still Working? - My Medicare Quotes, Medicare Adviser, Medicare Expert

Should I take Medicare at 65 if I’m still working? It’s one of the most common questions I receive from people approaching Medicare eligibility.

Over the years, I’ve spoken with many people who planned to keep working past age 65 and weren’t sure what to do next. Some wondered whether they should enroll in Medicare Part A, delay Part B, keep their employer coverage, or continue contributing to an HSA. The right answer isn’t always obvious, which is why understanding your specific situation is so important.

The answer depends on several factors, including the size of your employer, the cost of your employer coverage, whether your spouse is covered under your plan, and your future retirement plans.

I’ve been helping Medicare beneficiaries since 1985, and I’ve found that many people receive conflicting advice from friends, coworkers, and even their HR departments. Understanding how Medicare works with employer coverage can help you avoid costly mistakes and make a confident decision.

It Depends on the Size of Your Employer

One of the most important factors is how many employees your employer has.

Employers With 20 or More Employees

If your employer has 20 or more employees and your group health coverage is considered creditable, you can often delay Medicare Part B without facing a late enrollment penalty.

In many situations, your employer coverage remains primary, and Medicare can be delayed until you retire or lose that coverage.

Employers With Fewer Than 20 Employees

If your employer has fewer than 20 employees, Medicare generally becomes your primary coverage at age 65.

Failing to enroll in Medicare when first eligible could leave gaps in coverage and potentially expose you to late enrollment penalties.

Because every situation is different, it’s important to understand how your employer plan coordinates with Medicare.

Should You Take Medicare Part A?

Many people choose to enroll in Medicare Part A because most beneficiaries qualify for premium-free Part A.

Part A generally covers:

Hospital stays
Skilled nursing facility care
Hospice care
Certain home health services

However, there is one important exception.

What About Health Savings Accounts (HSAs)?

If you’re contributing to a Health Savings Account (HSA), enrolling in any part of Medicare generally means you can no longer make HSA contributions.

For some people, delaying Medicare enrollment while continuing HSA contributions may be the better choice.

This is an area where personalized guidance can be especially valuable.

Should You Delay Medicare Part B?

Medicare Part B covers services such as:

Doctor visits
Outpatient care
Preventive services
Durable medical equipment

If you have creditable employer coverage through a large employer, delaying Part B can help you avoid paying an unnecessary monthly premium.

However, if your employer coverage isn’t considered creditable, delaying Part B could result in penalties later.

Understanding the rules before making a decision is critical.

What If Your Spouse Is Covered Under Your Employer Plan?

Many people continue working because their spouse relies on employer coverage.

Questions to consider include:

Will your spouse lose coverage if you retire?
How much would Medicare cost compared to staying on the employer plan?
Would your spouse need alternative coverage?
Is COBRA a temporary option?

These decisions affect more than just you, which is why reviewing the entire family situation is important.

What Happens When You Retire?

When you eventually retire or lose employer coverage, you’ll generally qualify for a Special Enrollment Period to enroll in Medicare Part B.

This enrollment period allows you to sign up without incurring late penalties, provided you had qualifying employer coverage.

Timing matters.

Missing deadlines can lead to:

Lifetime late enrollment penalties
Delays in coverage
Unnecessary stress

Planning ahead can help make the transition smoother.

Common Mistakes to Avoid

After helping Medicare beneficiaries since 1985, I’ve seen several mistakes repeated over and over.

Assuming Medicare Is Automatic

Some people believe Medicare automatically coordinates with their employer coverage.

That’s not always true.

Ignoring Employer Size Rules

Whether your employer has more or fewer than 20 employees can significantly impact your decision.

Overlooking HSA Rules

Continuing HSA contributions after enrolling in Medicare can create tax complications.

Waiting Too Long

Missing enrollment deadlines can lead to penalties and gaps in coverage.

Frequently Asked Questions

Should I take Medicare at 65 if I’m still working?

It depends on your employer size, coverage, HSA contributions, and retirement plans. Many people can delay Part B, while others should enroll right away.

Can I delay Medicare Part B without a penalty?

Yes, if you have qualifying employer coverage through an employer with 20 or more employees, you may qualify for a Special Enrollment Period later.

Should I take Medicare Part A if I’m still working?

Many people enroll in premium-free Part A, but those contributing to an HSA may wish to delay enrollment.

What if my employer has fewer than 20 employees?

In many cases, Medicare becomes primary coverage at age 65, making timely enrollment especially important.

What happens when I retire?

You may qualify for a Special Enrollment Period that allows you to enroll in Medicare Part B without penalties if you’ve maintained qualifying employer coverage.

Contact The DeAngelis Agency

If you’re turning 65 and still working, I’d be happy to review your situation and help you understand your options.

Every employer plan is different, and making the wrong decision can have long-term consequences.

Call The DeAngelis Agency at 215-967-8828 to discuss your Medicare questions and determine the approach that makes the most sense for you.

Schedule Your Medicare Consultation Today

Medicare can be confusing, but getting answers shouldn’t be.

Whether you’re enrolling for the first time, reviewing your current coverage, considering a plan change, or simply looking for a second opinion, I’m happy to help you understand your options and answer your questions.

I’ve been helping Medicare beneficiaries since 1985, and I’ve built my practice on straightforward advice, long-term relationships, and treating people the way I’d want my own family treated.

If you’d like to discuss your Medicare options, call The DeAngelis Agency at 215-967-8828. There’s no pressure and no obligation—just honest guidance to help you make a confident decision.

Helping Medicare beneficiaries since 1985.

Should I Take Medicare at 65 If I’m Still Working?