Let me start with something important: Medicare should protect your retirement, not slowly drain it.
Yet every year, millions of good, hardworking people over 55 lose hundreds or even thousands of dollars simply because Medicare feels confusing, rushed, or overwhelming. These aren’t big, obvious mistakes. They’re small ones. Quiet ones. And that’s exactly why they hurt so much.
The good news? Once you understand a few simple rules, you can stop overpaying—and keep more of your money where it belongs.
Mistake #1: Choosing a Plan Once and Never Looking at It Again
Many people pick a Medicare plan when they first enroll and assume they’re set for life. But Medicare plans change every year. Premiums rise, drug coverage shifts, and doctors move in and out of networks. Meanwhile, your health and prescriptions change, too.
What this mistake costs: Higher monthly premiums, surprise copays, and paying for coverage that no longer fits your life.
The fix: Review your plan every year during Open Enrollment. Even a quick 20–30 minute comparison can uncover savings of $500 to $2,000 a year. Think of it like checking car insurance—you wouldn’t skip that, right?
Mistake #2: Overpaying for Prescription Drugs
This one catches almost everyone at some point. The same medication can cost wildly different amounts depending on your plan. Some people pay $10. Others pay $75. Same drug. Same pharmacy.
What this mistake costs: Hundreds—and sometimes thousands—every year.
The fix: Make sure your medications are listed on your plan’s formulary. Ask your doctor about generic alternatives. Compare prices at different pharmacies. And yes—when allowed, use discount programs. A five-minute check can mean real savings every single month.
Mistake #3: Paying for Extras You Never Use
Some Medicare plans advertise extras like vision, dental, gym memberships, or wellness perks. They sound great—but if you never use them, you’re paying for benefits that don’t help you.
What this mistake costs: Monthly fees that slowly chip away at your fixed income.
The fix: Choose a plan based on what you actually use, not what sounds nice in a brochure. Practical beats flashy every time.
Mistake #4: Missing Important Medicare Deadlines
Medicare has rules, timelines, and penalties—and they don’t always forgive honest mistakes. Miss a deadline, and you could face lifetime penalties added to your monthly premiums.
What this mistake costs: Higher bills for the rest of your life.
The fix: Mark your enrollment periods on your calendar. Set reminders. Ask questions early. One missed date can follow you forever—so don’t leave it to chance.
Mistake #5: Trying to Figure It All Out Alone
Medicare isn’t something most of us grew up learning. Yet people feel embarrassed asking for help—or assume help will cost money.
Here’s the truth: free, unbiased Medicare help exists.
The fix: Use licensed advisors, state health programs, or trusted comparison tools. Asking for help doesn’t lock you into anything—but it often saves a lot.
Medicare doesn’t need to be scary. You don’t need a finance degree. You don’t need to “get it perfect.” You just need to stay curious, ask questions, and review your options once a year.
Every dollar you stop overpaying is a dollar you can use for groceries, travel, hobbies, or peace of mind. And peace of mind matters.
That’s why I created The O55 Report—to turn complicated topics into clear, friendly guidance that actually helps real people. You worked hard for your retirement. Let’s make sure it works just as hard for you.
You’re not behind, you’re not alone, and it’s never too late to make smarter money moves.
With care,
Mike Bridges
Founder, The O55 Report