By Paul Barrett, CMIP | The Modern Medicare Agency Published: July 2026
I want to tell you about a phone call I got on a Tuesday afternoon in January.
A woman named Carol — she had just turned 66 — called me in a panic. She’d been on her husband’s employer plan for the past year, thought she had everything handled, and had just gotten off the phone with Social Security. They told her she owed a permanent Part B penalty for every month she hadn’t been enrolled.
She hadn’t done anything wrong on purpose. Nobody had told her the rules. She’d just assumed — reasonably, logically, completely understandably — that her husband’s coverage protected her.
It didn’t.
That call cost her roughly $40 more per month on her Part B premium. Forever. Not this year. Not until things get better. For the rest of her life.
I’ve been doing Medicare exclusively for 18 years. I’ve helped more than 5,000 people navigate this. And the thing that still gets me — the thing I genuinely cannot get used to — is that the mistakes I see most often aren’t complicated. They’re not obscure regulatory footnotes. They’re the same five situations, playing out over and over again, that nobody warned people about.
This article is my attempt to warn you before it’s too late
Mistake 1: Trusting COBRA Like It's a Get-Out-of-Jail-Free Card
This is the one that causes the most damage. I’ve seen it ruin retirements. I’ve seen it cost couples $20,000 in unnecessary penalties. And I see it every single year without exception.
Here’s what happens: someone retires at 65 (or older). Their employer offers them COBRA to continue their health coverage. They think, “Great — I’m covered. I have 18 months to figure out Medicare.” And they take it.
What they don’t know — what almost nobody tells them — is that COBRA does not count as creditable coverage for Medicare Part B.
The moment you retire and lose your employer coverage, your Medicare Initial Enrollment Period clock starts ticking. If you’re 65 or older and you take COBRA instead of enrolling in Medicare Part B, you are accruing a late enrollment penalty for every month you delay. And that penalty is 10% of your Part B premium for every 12-month period you were late. At 2026’s Part B premium of $202.90/month, a two-year delay adds $40.58 to your monthly premium. Permanently.
I’ve had clients call me after two, three, even four years on COBRA. By the time they figure out what happened, the damage is done and the Social Security Administration won’t reverse it.
The one exception worth knowing: If you are still actively employed (not retired) and covered by your current employer’s group health plan — or your spouse’s current employer’s plan — you can delay Part B without penalty. The key word is current. The moment you retire, that protection ends. COBRA is not current employer coverage. Retiree health benefits from a former employer are not current employer coverage. The protection applies only while you’re actively working.
Before you make any decisions about COBRA vs. Medicare, call someone who knows this inside and out. The conversation takes 15 minutes and it’s free. The mistake takes a lifetime to pay for.
Mistake 2: Choosing a Plan Based on the Monthly Premium
I understand why people do this. You get 20 mailers in October, they all have different prices, and you pick the one with the lowest number. It feels like comparison shopping. It makes sense.
It’s also one of the most reliable ways to end up in the wrong plan.
Here’s what I’ve learned after 18 years: the monthly premium is the least important number on the page. The numbers that actually determine what you’ll spend are the out-of-pocket maximum, the drug formulary tier for your specific medications, and — above everything else — whether your doctors are actually in-network.
Let me give you a real example. Someone picks a $0 premium Medicare Advantage plan because it looks like a deal. What they don’t notice is the $9,250 out-of-pocket maximum. They have hip replacement surgery eight months later. By year-end, they’ve paid $9,000 out of pocket. Their neighbor — who picked a plan with a $65 monthly premium and a $5,000 MOOP — paid $780 in premiums and $3,200 in cost-sharing. Total: $3,980. The person with the “free” plan paid more than double.
And that’s before we even get to the network problem.
The question that should come first — before we talk about premiums, before we look at a single plan — is: which doctors do you see, and what hospital would you go to if something serious happened? I run a live network search for every client before I mention a single plan name. Because a $0 plan that doesn’t cover your cardiologist isn’t a deal. It’s a liability.
I’ve watched people pick the lowest premium plan in October, get their surgery scheduled in February, and discover in March that their surgeon is out-of-network. That’s not a hypothetical. That’s a Tuesday.
Mistake 3: "Set It and Forget It" , Never Reviewing Your Coverage
Medicare is not a one-time decision. It’s an annual decision. And the number of people who enroll in a plan at 65 and never look at it again is staggering.
Here’s why this matters: every October, your plan sends you something called an Annual Notice of Change (ANOC). It’s a document — sometimes thick, often confusing — that tells you exactly what’s changing about your plan on January 1. Premiums, copays, networks, drug formularies. Everything that might be different next year.
Most people throw it away.
I can’t tell you how many times I’ve sat with a client who was blindsided by a January 1 change they could have prepared for. Their prescription moved from Tier 2 to Tier 4. Their doctor left the network. Their plan raised its out-of-pocket maximum by $1,200. Their pharmacy was reclassified from preferred to standard. Every one of these things was disclosed in that ANOC. Every one of them was a surprise because nobody read it.
Here’s the thing: your needs change too. The plan that was perfect at 65 might not be the right plan at 72. New medications, new specialists, new health conditions — all of these affect which plan is actually the best fit for your current life. An annual review isn’t bureaucracy. It’s protection.
I do free annual reviews for every client I’ve ever enrolled. That’s not charity — that’s the job. If your agent isn’t doing this, you have the wrong agent.
Mistake 4: Skipping Part D Because "I Don't Take Any Medications"
I have this conversation more than you’d think. Someone is turning 65, they’re healthy, they don’t take any prescriptions, and they decide to skip Part D drug coverage to save the monthly premium.
I get the logic. Why pay for something you don’t need?
Here’s the problem: the late enrollment penalty for Part D is calculated on every month you went without creditable drug coverage. The penalty is 1% of the national base beneficiary premium ($38.99 in 2026) per uncovered month — permanently added to your Part D premium for as long as you have Medicare.
Go 24 months without Part D and you’re paying an extra $9.36/month forever. Go 36 months and it’s $14.04/month. These numbers seem small until you run the math over a 20-year retirement.
But the bigger issue isn’t the penalty. It’s what happens to people’s health between 65 and 70. I’ve watched people skip Part D at 65 because they were healthy — and then get diagnosed with something significant at 68. Suddenly they need medications. Now they have to enroll in Part D during the next available window, pay the penalty for every month they went without coverage, and hope that whatever they need is on the formulary of whatever plan is available to them.
There are Part D plans available for under $20/month. Some are even lower. Enrolling is protection against a future you can’t predict — and insurance works by buying it before you need it, not after.
Mistake 5: Getting Advice from Someone Who Only Represents One Company
This one is the hardest to talk about because it sounds self-serving. I’m an independent broker. Of course I’m going to tell you that independence matters.
But let me tell you what I’ve actually seen — not as a pitch, but as a description of real situations I’ve had to help people out of.
I’ve talked to people who called a 1-800 number from a TV commercial and enrolled in whatever plan the person on the phone offered. They didn’t know that the person they were talking to was a captive agent for one company with one lineup of plans. They didn’t know there were 27 other plans available in their area that never came up in that conversation.
I’ve had clients come to me after enrolling with a carrier-direct agent who told them their doctor was “probably” in-network. Probably. They didn’t check. By January 15, the client’s specialist of ten years was out-of-network and they were facing out-of-network cost-sharing for ongoing cancer treatment.
I’ve sat with people who enrolled in a $0 premium plan because the person who helped them got a higher commission on that plan — and never mentioned that a $40/month plan with a $3,000 lower out-of-pocket maximum would have saved that client money in any year they actually needed care.
Here is what independence actually means in practice: when I sit across from someone — whether it’s in person, by phone, or on Zoom — I have access to every plan available in their area from every carrier I represent. I have no quota. No commission override that pays me more for one carrier than another. No manager pushing me toward this month’s “featured plan.”
I show people what’s actually best for their situation. Sometimes that’s the plan with the highest commission. Sometimes it’s the lowest. I recommend High Deductible Plan G regularly — even though it pays me less than standard Plan G — because for the right client, it’s the right answer.
That’s what you’re supposed to get when you call someone who works for you instead of an insurance company.
Why These Mistakes Keep Happening
I’ve thought about this a lot over 18 years.
The Medicare system is genuinely complicated. The rules are written in bureaucratic language. The enrollment windows are strict and the penalties are permanent. The marketing is relentless and often misleading. And most people only do this once — maybe twice if they need to make a change — so they don’t have the experience base to know what they don’t know.
There’s also this: people are often turning 65 at the same time they’re managing a lot of other major life transitions. Retirement. Changes in income. Shifts in relationships. Maybe an aging parent who needs care. Medicare decisions land in the middle of all of that.
The combination of complexity, high stakes, and timing makes these mistakes almost predictable. They happen to smart, capable, responsible people who simply weren’t given the right information at the right time.
That’s what I’m trying to fix, one conversation at a time.
What To Do Instead
None of the five mistakes I’ve described is hard to avoid — if you know about them before they happen.
On the COBRA question: Before you make any retirement coverage decisions, call me or another independent Medicare broker who specializes in this. Walk through the timing. Understand when your IEP starts and what qualifies as creditable coverage. Don’t assume. The conversation is free.
On premium shopping: Bring me your doctors’ names, your medications, and your pharmacy before we look at a single plan. We build from your situation outward — not from a rate sheet inward.
On annual review: October is the month. Every year. Read your ANOC. Or call me and I’ll read it with you. It takes 20 minutes and it can save you thousands.
On Part D: If you’re healthy and not taking medications, enroll in the least expensive creditable Part D plan available in your area. Think of it as protection for your future self, not coverage for your current self.
On who you work with: Ask your agent how many carriers they represent. Ask whether they’re captive or independent. Ask how they’re paid. An agent who won’t answer those questions is telling you something important.
A Final Thought
Carol — the woman from that January phone call — eventually got her Medicare situation sorted out. She couldn’t undo the penalty, but she found a Medigap plan that fit her situation well, got her Part D enrolled, and has had good coverage since then.
But every month when she pays that slightly higher Part B premium, she thinks about that conversation with Social Security. She told me that herself.
I don’t share that to make anyone feel bad. I share it because that phone call — and the hundreds like it I’ve received over 18 years — is the reason I write things like this. The system is complicated enough without people walking into it without a map.
You deserve to get this right the first time.
If you have questions — about any of this, about your specific situation, about whether you’re about to make one of these mistakes — call me. That conversation is always free. Always honest. And I’ve been doing this long enough to have seen almost everything.
Paul Barrett, CMIP The Modern Medicare Agency 📞 631-358-5793 ✉️ medicare@paulbinsurance.com 🌐 paulbinsurance.com 📍 445 Broad Hollow Rd, Melville, NY 11747
Related reading:
- Medicare Enrollment Mistakes That Can Cost You for Life
- Medicare Advantage vs. Medigap: The Honest Side-by-Side Nobody Else Will Show You
- Medicare for Dummies 2026: The Simple No-Stress Guide
- Original Medicare Explained: Your 2026 Coverage Guide
- When Is the Best Time to Switch Medicare Supplement Plans?
- Medicare Supplement Plan G: Complete 2026 Guide
Disclaimer: The Modern Medicare Agency is not connected with or endorsed by the United States government or the federal Medicare program. This article is for educational and informational purposes only. Medicare rules and costs referenced reflect 2026 CMS-published figures. Individual situations vary — consult a licensed Medicare specialist before making any coverage decisions.
