The $1,200 Wake-Up Call

A few years back, I got a call from a woman named Janet who had just retired after 40 years in education. She was sharp, organized, and had always handled her benefits like a pro. But that call wasn’t a happy one.

She was sitting at the pharmacy counter, trying to pick up her blood pressure medication, when she was told her prescription wasn’t covered — because her Medicare Part D plan hadn’t started.

The look on her face must’ve said it all. She called me in a panic.

Turns out, Janet thought she was “automatically enrolled” in everything when she turned 65. She had signed up for Social Security, so she assumed Medicare came with it. But she delayed enrolling in a drug plan (Part D) because she “wasn’t taking much” and didn’t think she needed it yet.

That choice — waiting a full year to enroll — triggered a 12% late enrollment penalty on her Part D premiums. And here’s the kicker: That penalty doesn’t go away. It sticks with you for life. If you're unsure whether you need it now, learn more about understanding Medicare Part D coverage.

Between that and a brief gap in drug coverage, she ended up spending over $1,200 more than she needed to — all because she didn’t have the full picture.

And she’s not alone.

Most people I talk to who are nearing retirement assume Medicare is simple — until they find out too late that it’s full of deadlines, rules, and hidden costs.

That’s why I wanted to share this story — and a few clear, simple tips to help you avoid the most common (and expensive) Medicare mistakes.

If you're retiring soon or turning 65 in the next 6 months, keep reading. I promise this will save you time, stress, and possibly thousands of dollars down the line.

Your Medicare Enrollment Window Is Ticking

One of the most common things I hear from people approaching retirement is:

“I’m not quite 65 yet — I’ve got time, right?”

And technically, yes — but the clock starts ticking earlier than most folks realize.

Here’s How the Medicare Timeline Works:

Your Initial Enrollment Period (IEP) is a 7-month window that only opens once.

• It starts 3 months before the month you turn 65
• Includes your birthday month
• And extends 3 months after

Let’s say your birthday is in October — your window runs from July through January.

If you sign up during the 3 months before your birthday month, your coverage starts right on time. If you wait until your birthday month or later, your coverage could be delayed — and that delay could leave you with gaps in coverage and potential penalties.

But Here’s Where People Get Tripped Up:

Some people think, “I’m still working, so I’ll deal with Medicare later.” That might be okay — if you’re still actively working and covered by a large employer group plan (more on that in the next section).

But if you're not covered by active employer insurance — like if you're retiring or losing coverage — that delay could come back to bite you.

Another misunderstanding I hear often is:

“I’ll just sign up for Medicare when I need it.”

Unfortunately, that’s not how Medicare works. It's not like turning on Netflix when you're ready to watch a show. If you miss your IEP and don’t have creditable coverage, you could be looking at late enrollment penalties and waiting until the General Enrollment Period (which only runs from January to March each year) — with coverage not starting until July.

That’s a long time to go without coverage when you might need it most.

Even if you’re unsure whether to enroll in Parts A, B, D, or get a Medicare Supplement vs Advantage plan — start learning early. It’s a lot easier to make the right choice when you’re not rushing against a deadline.

What Happens If You Miss the Deadline?

You’d be surprised how many people find out after the fact that Medicare doesn’t just "kick in" when you need it.

Missing your enrollment window might not feel like a big deal at first… until the penalties start piling up, your coverage is delayed, and the stress kicks in.

Let’s break it down.

The Cost of Waiting: Permanent Penalties

Medicare has two main penalties you need to watch out for — and they’re not just one-time fees. These stick with you for life.

Part B Late Enrollment Penalty

If you don’t sign up for Medicare Part B (medical insurance) during your Initial Enrollment Period (and you don’t have creditable coverage), you’ll pay:

• 10% more on your monthly premium
• For every 12-month period you delayed enrollment
• For the rest of your life

Example: If you wait 2 years, that’s a 20% permanent increase in your Part B premium. In 2025, that could be an extra $36+ per month — forever.

Part D Late Enrollment Penalty

This one catches even more people off guard, because they think, “I’m not on any meds yet — I’ll skip it.”

Here’s what happens:

• You’ll pay 1% of the national base premium for every month you delay Part D enrollment
• That’s .01 x number of months late
• And yes, it’s added to your monthly drug plan premium — forever

Example: If you wait 12 months to sign up, your penalty is 12% more every month — even if you later pick a low-cost plan.

Real Talk: I’ve Seen It Too Many Times

One client, Ed, decided to retire at 66. He figured, “I’m healthy, I’ll just wait on Part B and D until I really need them.” Fast-forward a year and he was having some heart trouble. That’s when he learned:

• He’d have to wait until January to enroll
• His coverage wouldn’t start until July
• And he’d now pay extra every month — for life

It wasn’t just frustrating — it was scary. He needed medical care now, but Medicare wasn’t kicking in for another 6 months.

Bottom Line:

If you miss your Medicare window and don’t have qualified insurance through work or a spouse, you’re looking at:

• Higher premiums — permanently
• Delayed coverage — up to 6 months
• Stress and regret — when you should be focused on enjoying retirement

Coming up next: we’ll tackle one of the most confusing situations.

“But I Have Employer Coverage” — Are You Really Safe?

This is where things get tricky — and where a lot of folks unknowingly step into the Medicare penalty zone.

Every week, I talk to someone who says something like:

“I’m still working past 65, and I’ve got insurance through work, so I don’t need Medicare yet, right?”

Maybe. But let’s make sure — because the rules aren’t one-size-fits-all.

Rule #1: Are You Actively Working AND Covered by a Large Employer Plan?

If you're still working and your employer has 20 or more employees, you're usually safe to delay Part B and Part D without penalty.

But the moment that coverage ends — because you retire, get laid off, or drop your plan — your Medicare clock starts ticking fast.

You’ll then enter a Special Enrollment Period (SEP), which gives you 8 months to sign up for Part B without penalty. But here’s what catches people off guard:

• That 8-month window starts the day your group health coverage ends, not when you “feel like enrolling.”
• And if you go even one day without creditable drug coverage, the Part D penalty kicks in too.

Rule #2: COBRA and Retiree Plans Are NOT the Same as Employer Coverage

Here’s a big mistake I’ve seen too many people make.

A guy I helped recently, Ken, had just retired and was on COBRA for 18 months. He assumed he didn’t need to sign up for Medicare until COBRA ended.

He was wrong — and it cost him.

COBRA isn’t considered creditable coverage for Medicare. Neither are retiree-only health plans. That means if you’re past 65 and on either of those without enrolling in Medicare?

• You’re racking up penalties.
• You’re not fully covered.
• And when you do apply, you might have to wait months for coverage to start.

How to Know You’re in the Clear

To be safe, take these three quick steps:

1. ✅ Ask your HR rep if your coverage is creditable for Medicare — especially Part B and Part D.
2. 📄 Request it in writing. This “Creditable Coverage Letter” can save you down the line.
3. 📞 Talk to a licensed Medicare agent (like us) who can review your situation and make sure you’re not setting yourself up for penalties.

Quick Recap:

How to Avoid the Trap

By now, you’ve probably realized that Medicare isn’t exactly plug-and-play. The rules, deadlines, and exceptions can sneak up on you — and the cost of getting it wrong can add up fast.

But the good news? Avoiding all the headaches is totally doable. You just need a simple plan — and a little lead time. Our free Medicare checklist before turning 65 makes it easy to stay organized and avoid last-minute stress.”

So here’s your 3-step game plan to make sure you stay covered, penalty-free, and stress-free.

Step 1: Mark Your Medicare Timeline Early

I always tell people: put it on your calendar 6 months before your 65th birthday.

Why 6 months? Because it gives you time to:

• Learn your options
• Check your current insurance situation
• Make informed decisions without scrambling

Example: If you turn 65 in October, you’ll want to start your Medicare prep by April — even if you’re not planning to retire right away.

This gives you a head start before your Initial Enrollment Period even opens.

Step 2: Talk to HR — and a Real Medicare Advisor

If you’re still working, the first call you make should be to your HR department.

Ask them:

• Is my current health plan considered creditable for Medicare?
• Do I need to enroll in Part B or Part D now?
• What happens to my coverage when I retire?

Then talk to someone who actually works with Medicare every day (hint: that’s us). A licensed agent can look at your situation and help map out:

• Whether you can safely delay any parts of Medicare
• When you need to act to avoid penalties
• What plan options fit your lifestyle, budget, and health needs

Step 3: Enroll Early — Don’t Wait Until the Last Minute

Once you know it’s time to enroll, don’t wait until your birthday month to do it.

Why?

• If you enroll early (in the 3 months before your 65th birthday), your coverage starts right on time.
• If you enroll during or after your birthday month, your coverage might be delayed by 1 to 3 months.

And let’s be honest — nobody wants to find out their coverage hasn’t kicked in yet when they’re standing at the doctor’s office or pharmacy counter.

Pro Tip:

Even if you’re healthy and don’t take any prescriptions, it’s still a good idea to enroll in a low-cost Part D drug plan — (and if you're wondering which direction to go, compare Medicare Supplement and Advantage plans to see what’s right for your situation) — just to avoid the penalty. Some plans cost less than $10/month, which is a small price to pay for lifelong protection.

Absolutely — here’s Section 5, offering helpful tools and support in a warm, reassuring tone that empowers the reader to take the next step:

Tools to Make It Easy

Let’s be honest — Medicare can feel like a maze. Between Parts A, B, D, Medigap, Advantage plans, deadlines, and penalties… it’s no wonder people feel overwhelmed.

But here’s the good news: you don’t have to figure it out alone.

Whether you're a checklist lover, a "just tell me what to do" type, or somewhere in between — there are simple tools that can take a mountain of confusion and break it into manageable steps.

1. The Medicare Retirement Checklist

We created a free, printable checklist that walks you through everything you need to do — and when to do it — based on your situation.

It covers:

• When to enroll (based on age, work status, and coverage)
• What documents you’ll need
• How to compare plan types without losing your mind
• What to ask HR before you retire

Want it? [Click here to download your Medicare Retirement Checklist]

2. Quick & Easy Medicare Quiz

Still not sure whether you need a Medicare Supplement or Advantage plan? Not even 100% clear on the difference?

We made a short, no-pressure quiz to help point you in the right direction — based on your preferences, doctors, travel habits, and medication needs.

It only takes about 2 minutes, and it gives you a clear recommendation based on your answers.

👉 [Take the quiz here]

3. Talk to a Real Person Who Gets It

If there’s one thing I’ve learned after helping thousands of people navigate Medicare, it’s this:

Sometimes, you just need to talk to someone who knows what they’re doing.

Not a call center. Not a robot. A real advisor who listens, explains things in plain English, and helps you make the right choice for you.

That’s exactly what we do here at Lehigh Partners. We’ve helped folks in every situation — from retiring teachers and truck drivers to small business owners and snowbirds heading to Florida.

No sales pressure. No jargon. Just honest guidance from someone who’s been through it with hundreds of clients before you.

Want to Talk One-on-One?

You can book a free consultation call at a time that works for you. No commitment — just answers and clarity.

👉 [Schedule your free Medicare call here]

Coming up next: In the final section, I’ll revisit Janet’s story — and leave you with a simple takeaway that can help you dodge the $1,200 mistake others have made.

CONCLUSION: Learn From Their $1,200 Mistake — Don’t Repeat It

Let’s go back to Janet for a moment.

She didn’t forget to enroll because she was careless. She didn’t delay her Medicare drug coverage because she was lazy. She just didn’t know. Like so many others, she assumed Medicare would be simple — and that she’d be automatically protected.

That innocent misunderstanding cost her over $1,200 in penalties and uncovered prescriptions — not to mention a whole lot of stress during what should’ve been a peaceful start to retirement.

But you? You’re already ahead of the curve.

You now know:

• When your enrollment window opens — and why timing matters
• What penalties exist and how to avoid them
• How employer coverage does and doesn’t protect you
• And most importantly, where to go for clear, honest help

Medicare might feel overwhelming, but it doesn’t have to be.

Your Next Step: Clarity Over Confusion

If you're turning 65 soon or planning to retire in the next 6 months, don’t roll the dice. You’ve got one shot at getting this right the first time.

Whether you just want a checklist, a quick quiz, or a one-on-one conversation, we’re here to help you every step of the way.

👉 Click here to schedule your free Medicare review — and breathe easy knowing you’re not walking into this alone.

Because peace of mind in retirement starts with making the right decisions today.