5 Medicare Mistakes to Avoid in 2026 (Especially If You’re Turning 65)

Medicare isn’t “set it and forget it.” A wrong tur, like assuming it’s free, missing a deadline, or trusting a slick ad—can cost thousands and limit your future options. Here are the five mistakes I’ve seen over and over in 20+ years, and how to avoid them so you keep your doctors, control costs, and sleep better at night.

Key Takeaways

• Medicare isn’t free. Part B and Part D have premiums and potential penalties if you delay.
• Ads don’t tell the whole story. $0-premium Advantage plans still have rules, networks, and annual out-of-pocket limits.
• “I’ll switch later” can backfire. After your initial Part B window, Medigap applications can ask health questions.
• Deadlines are unforgiving. Miss the Initial Enrollment Period or AEP and you may face penalties or be locked in.
• You need a coach, not a closer. Get unbiased guidance so the plan fits you, not a commission schedule.

Mistake #1: Thinking Medicare Is Free

Yes, Part A is usually premium-free if you or a spouse worked ~10 years. But Part B has a monthly premium (about $185 in 2025, likely higher in 2026 per the video), and Part D has its own premium. Plus late-enrollment penalties if you delay. Higher-income enrollees may also pay IRMAA surcharges on Parts B and D.

The biggest shocker? Original Medicare has no out-of-pocket maximum. Without a Medigap or Medicare Advantage plan, there’s no cap on what you might pay in a bad year.

Mistake #2: Choosing a Plan Based on Ads or “Free Stuff”

$0 premium doesn’t mean $0 cost. Many Medicare Advantage plans use provider networks, referrals, and prior authorization rules. And while the premium may be $0, CMS’s mandatory in-network MOOP is $9,350 for 2025 and $9,250 for 2026.

Medigap generally costs more per month and you’ll add a standalone Part D plan, but you typically get broader access and more predictable costs. The real mistake is picking either route because it sounds cheap or expensive. Choose based on your doctors, meds, travel, and risk tolerance.

Mistake #3: Assuming You Can “Switch Later” Without Consequences

When you first enroll in Part B, you get a 6-month Medigap open window with no health questions. After that, most states allow underwriting. Insurers can ask about health and may deny or rate up.

There are exceptions (state-specific rules and a 12-month “free look” if you try MA and switch back to Medigap in time), but don’t bank on a later do-over. If Medigap is likely important to you, your best chance is at the start.

Mistake #4: Missing Critical Medicare Deadlines

Initial Enrollment Period (IEP): 3 months before your 65th birthday month through 3 months after. Miss it and you can face permanent Part B/D penalties.

Working past 65? You may have a Special Enrollment Period when employer coverage ends. COBRA usually doesn’t count as active coverage for Medicare.

Already on Medicare? Your annual chance to review/switch Advantage or Part D plans is Oct 15–Dec 7 (AEP). Miss it, and you could be locked in for another year.

Mistake #5: Letting a Sales Pitch Decide for You

There are great agents, and there are high-pressure call centers. Most big advertisers are built to enroll, not to educate. You don’t need a pitch to make a smart decision; you need clear rules, trade-offs, and a plan that fits you.

What To Do Next

List your must-haves: doctors, hospitals, meds, travel, budget, and how much risk you’re comfortable carrying.

Decide on your route first: Medigap + Part D vs. Medicare Advantage. Based on your needs, not commercials.

Mark your dates: IEP, any SEP if you’re working past 65, and AEP (Oct 15–Dec 7).

Get unbiased help: Talk to a licensed, independent advisor who’ll walk you through pros/cons without pressure.

If you want a straightforward walkthrough, start with my book and courses. If you prefer one-on-one help, connect with an independent advisor who will compare your options side-by-side.

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