How to Transition from Employer Insurance to Medicare—Without Costly Mistakes

Let’s be real—switching from your employer insurance to Medicare can feel like a nightmare and confusion all in one. There are deadlines, different plan options, and a million rules that no one explains clearly. And if you get it wrong? It could mean penalties, higher costs, or losing access to your doctors.

As a broker, I talk to people every day who say, “I wish someone had told me this BEFORE I left my job.” So let’s break it down and simplify this so you feel confident and in control of your Medicare choices.

First, Let’s Talk About Timing -- Because This is Where Most People Get Stuck!

Imagine you’re about to leave your job. You’re used to having your employer handle health insurance, but now it’s on you to make sure you don’t have a gap in coverage.

When Do You Have to Enroll in Medicare?

?? If you’re turning 65 and retiring, you have a 7-month window to enroll (3 months before your birthday, the month of, and 3 months after).

?? If you’re already 65 and leaving employer insurance, you have an 8-month Special Enrollment Period (SEP) to sign up for Medicare after your employer coverage ends. ?? BUT—you only have 2 months to pick a Medicare Advantage or Part D plan. Most people MISS this.

Now let me ask you: Are you still working? Do you have employer coverage? Because that changes things…

?? Here's what you need to know if you're planning of working beyond age 65....

Here's the thing, a lot of people keep working past 65. Maybe you love your job, or maybe you just want to stack more retirement cash. Either way, the big question is:

Do I HAVE to take Medicare now, or can I STAY on my work insurance?

?? If your company has 20+ employees, you can delay Medicare without penalties. But you’ll still want to compare costs—sometimes Medicare is actually the better deal!

? If your company has fewer than 20 employees, Medicare becomes your primary insurance at 65. That means you NEED to enroll in Part A and Part B to avoid gaps in coverage.

?? Here's a Tip: Ask HR for a letter stating your coverage is creditable (this protects you from penalties later).

So, are you planning to retire soon, or are you still working?

Let's transition here...

?? Medicare Options: What’s Most Like Your Job’s Insurance?

Now, I get this question a LOT:

I had great employer insurance… which Medicare plan feels the most like what I had at work?

Here’s the deal: You have TWO main paths.

Option 1: Original Medicare + Medigap (Supplement) + Part D

? See any doctor nationwide—no networks. ? Medigap plans cover most or all out-of-pocket costs. ? Separate Part D plan for prescriptions. ? Higher monthly costs upfront, but little to no medical bills later.

This option is best for people who want predictable costs and nationwide coverage.

Option 2: Medicare Advantage (Part C)

? Works more like an HMO or PPO (network-based). ? Lower premiums (some as low as $0/month). ? Often includes dental, vision, and hearing benefits. ? Copays and out-of-pocket costs apply when you receive care. ? You must stay in-network for most care.

This option is best if you’re comfortable with networks and want lower upfront costs.

So let me ask—do you prefer lower monthly costs but copays when you go to the doctor, or would you rather pay a little more upfront and not worry about big medical bills later? I want to hear from you in the comments!

?? Now What About COBRA? This is Where People Get in Trouble!??

I have to say this LOUDLY—COBRA is NOT Medicare.

A lot of people think, “I’ll just stay on COBRA instead of signing up for Medicare.” Big mistake.

?? COBRA does NOT count as creditable coverage for Medicare. If you stay on COBRA and don’t enroll in Medicare on time, you could end up with a permanent late penalty.

?? COBRA is ridiculously expensive. Now that your employer isn’t covering part of the cost, you’re paying 100% of the premium—plus a 2% fee. That could mean $600-$1,000+ per month! -- trust me, I've once considered it myself.

?? COBRA and Medicare don’t work well together. If you enroll in Medicare while on COBRA, Medicare pays first, and COBRA may stop covering your medical bills.

Were you thinking about using COBRA instead of Medicare? If so, let’s talk, because I can almost guarantee there’s a better option.

?? What’s Your Next Move?

I know this is a LOT of information. And the truth is—there’s no one-size-fits-all answer.

The best Medicare plan for you depends on: ?? Your health – Do you see doctors regularly or take multiple prescriptions? ?? Your budget – Do you want lower upfront costs or lower medical bills later? ?? Your doctors – Do they accept Medicare? Are you okay with a network?

The worst thing you can do? Guess your way through this. Medicare mistakes are expensive and hard to fix.

?? Need help? Let’s talk. Drop a comment, send me a message, or book a quick call. I’ll help you figure out the best plan for YOU—without all the confusion.

Talk Soon!