3 Medicare Traps That Could Wreck Your Retirement (And How to Avoid Them)

Trap #1: Missing Your Medicare Enrollment Window

This is hands-down the most dangerous Medicare mistake—and one of the easiest to avoid.

Here’s how it works:

If you’re turning 65 and not already taking Social Security, you need to actively enroll in Medicare. You don’t get enrolled automatically unless you’re drawing Social Security benefits.

You have a 7-month Initial Enrollment Period:

• Starts 3 months before your 65th birthday month
• Includes your birthday month
• Ends 3 months after

If you miss that window?

You may have to wait until the next General Enrollment Period (January 1 – March 31), and your coverage might not start until July 1. Even worse, you’ll face a 10% late enrollment penalty on your Part B premium for every 12-month period you delayed—and that penalty is permanent.

We’ve had clients come to us months after turning 65, completely unaware they needed to sign up—and now they’re stuck with gaps in coverage and lifetime penalties.

How to avoid it:

Even if you’re still working or covered under your spouse’s plan, talk to a licensed Medicare agent to confirm the right timing for your enrollment.

Trap #2: Choosing the Wrong Plan Upfront—and Getting Stuck

Many people choose a Medicare Advantage plan because it looks simple and has a $0 premium. But here’s the catch: if you develop health issues later and want to switch to a Medicare Supplement plan, you may be denied coverage.

Here’s why:

Most states only allow you to enroll in a Medigap plan without medical underwriting during your Initial Enrollment Period. After that, if you want to switch, you’ll typically need to go through health underwriting—and you can be denied coverage for certain pre-existing conditions like:

• Cancer
• Heart disease
• Stroke
• Insulin-dependent diabetes
• And even certain prescriptions

We’ve seen retirees stuck on Advantage plans they no longer want, paying thousands in out-of-pocket costs, simply because they missed their opportunity to switch when they were healthy.

How to avoid it:

When you first enroll in Medicare—whether at 65 or after leaving employer coverage—consider your future health needs, not just what works for today. It’s usually best to start with a Medigap plan like Plan G or N if you can afford it and qualify.

Trap #3: Only Looking at Monthly Premiums

Many people get caught up in finding the lowest monthly premium—but they forget to look at the total cost of the plan, including:

• Deductibles
• Copays for doctor and specialist visits
• Coinsurance for hospital stays, surgeries, and treatments
• Out-of-pocket maximums
• Prescription drug costs
• Network restrictions

For example, a $0 premium Medicare Advantage plan might sound great—until you’re hospitalized or diagnosed with a chronic condition. We’ve seen clients rack up $6,000+ in a single year from hospital stays, chemotherapy, or specialist visits—all because they didn’t factor in the hidden costs of their plan.

And don’t forget travel coverage—if you leave your home area or state frequently, you need to make sure your plan still covers you.

How to avoid it:

Don’t fall into the trap of comparing only monthly premiums. Compare the total cost of each plan based on your personal health needs, doctor usage, medications, and travel habits.

Recap: The 3 Medicare Traps You Must Avoid

Let’s quickly review the three biggest Medicare traps that could cost you thousands—or even leave you without the coverage you need.

1. Missing Your Enrollment Window

• You only have 7 months around your 65th birthday
• Miss it, and you face permanent penalties and delayed coverage

2. Choosing the Wrong Plan First

• Enrolling in a Medicare Advantage plan is easy
• Switching to a Medigap plan later may not be possible if your health declines

3. Focusing Only on Premiums

• $0 premium doesn’t mean $0 cost
• Know your total cost exposure before enrolling in any plan

Bonus Tip: Get Personalized Help Before You Enroll

There’s no one-size-fits-all Medicare plan. Your health, your doctors, your prescriptions, and your travel needs all matter. Whether you’re just turning 65 or retiring and leaving employer coverage, it pays to get expert advice before you enroll.

Get Free Medicare Help Today

If you want help avoiding these traps and making sure you get the best Medicare coverage for your situation, we’re here to help.

Call us at 800-208-4974 to book your free Medicare consultation.

We’ll help you:

• Avoid enrollment mistakes
• Compare Medigap and Advantage options
• Review your doctor and prescription coverage
• Find the best plan for your needs and budget