Should You Enroll in Medicare at 65 If You’re Still Working?

Some days, the universe just wants me to talk about Medicare.

It started with a text from a friend: “Hey, I turn 65 in a few months. Do I HAVE to sign up for Medicare if I’m still working?” Not two hours later, another friend—completely unrelated—emailed me with almost the exact same question. Coincidence? Maybe. But when two different people hit me up with the same question on the same day, I take it as a sign. So, let’s talk about it.

If you’re about to hit that magic age of 65, and you’re still happily (or even unhappily I guess) employed, should you jump into Medicare, or can you keep things exactly as they are? The answer, as always, is: It depends. Let me break it down without all the headache-inducing jargon.

Big Question #1: Is Your Employer Big or Small? (This Changes Everything)

Here’s the first and most important rule: Medicare and employer insurance don’t always play nicely together.

• If your employer has 20+ employees, your company’s health plan remains your primary insurance. That means you can delay signing up for Medicare Part B (which covers outpatient care and comes with a monthly premium) without penalty.

• If your employer has fewer than 20 employees, it’s the opposite—Medicare becomes your primary coverage, and your employer plan only picks up what Medicare doesn’t cover. This means you must enroll in Medicare Part A & B to avoid major gaps in coverage.

So, your first assignment is to ask HR how your plan coordinates with Medicare. The size of your employer determines whether Medicare is optional or mandatory.

Small business employees, pay attention! If your company has fewer than 20 employees and you don’t enroll in Medicare at 65, your job’s insurance could refuse to pay claims—leaving you stuck with the bill. And trust me, hospital bills aren’t the kind of surprise you want in retirement.

Big Question #2: Just Because You Can Delay Medicare, Should You?

Alright, let’s say you work for a big company and technically don’t have to enroll in Medicare yet. Should you? Let’s weigh your options.

Reasons to Enroll in Medicare at 65 Even If You’re Still Working:

• Your work insurance is expensive – Some employer plans have sky-high premiums and deductibles. Medicare might actually save you money.

• Your employer plan has a limited network – Medicare often gives you more choices when it comes to doctors and hospitals.

• You travel a lot – Medicare covers you anywhere in the U.S., while some employer plans are state-restricted.

• It’s (kind of) free– Medicare Part A (which covers hospital stays) is free for most people. There’s no downside to enrolling, unless…

🚨 The Big Exception: Do You Have an HSA? If you have a Health Savings Account (HSA) and want to keep contributing, DO NOT sign up for Medicare Part A or B just yet. Once you enroll in any part of Medicare, you can no longer contribute to an HSA—and there are tax penalties if you do.

Reasons to Delay Medicare Until You Retire:

• Your employer plan is better and cheaper – If your job’s coverage is great, there’s no point in adding Medicare into the mix just yet.

• You don’t want extra premiums – Medicare Part B costs money every month. Why pay for it if your job already gives you solid coverage?

• You plan to keep working for a while – If retirement is years away and your employer plan is doing just fine, Medicare can wait.

Bottom line? Do the math. Compare your employer plan costs with Medicare’s costs before deciding.

Big Question #3: What Happens If You Mess This Up? (Aka, Avoiding Late Penalties)

I get it—government paperwork is no one’s favorite thing. But trust me, you do NOT want to ignore Medicare enrollment if you’re supposed to sign up. If you delay Part B when you weren’t supposed to, you could be hit with a permanent late enrollment penalty—meaning your Medicare premiums will be higher for the rest of your life.

Even worse? If you miss your initial window, you’ll have to wait for the General Enrollment Period (January–March), which means you could be stuck without coverage for months.

So, if you’re not sure whether you need to enroll, ASK. Talk to your employer, check with Medicare, or better yet—reach out to an expert before it’s too late.

So What Should You Do?

If you’re still working at 65+, Medicare isn’t one-size-fits-all. The right move depends on:

1. How big your employer is

2. How good your current health plan is

3. Whether you have an HSA

4. When you actually plan to retire

   
   

My best advice? Call your HR department and consult a Medicare expert, such as a SHIP (State Health Insurance Assistance Program) counselor or an independent Medicare advisor before making a move.

Still confused? Drop a comment or shoot me a message. Because if two people asked me today, I know plenty of you have to be wondering the same thing.