7 Mistakes You're Making with Medicare Planning (and How to Fix Them Before Open Enrollment Ends)

Medicare Open Enrollment is happening right now through December 7, 2025, and if you're like most people approaching or already on Medicare, you might be making critical mistakes that could cost you thousands of dollars and leave you with inadequate coverage. At Borde & Associates, we've helped countless families navigate these complex waters over the years, and we've seen the same costly errors repeated time and again.
The good news? You still have time to fix these mistakes before the enrollment window closes. Let's walk through the seven most common Medicare planning errors and show you exactly how to correct them before it's too late.
Mistake #1: Misunderstanding What Medicare Actually Covers
One of the biggest misconceptions we encounter is that Medicare covers everything you need once you turn 65. This simply isn't true, and this misunderstanding can leave you facing substantial medical bills.
What's Missing:
- Original Medicare (Parts A and B) typically covers only about 80% of your healthcare costs
- Long-term care, dental, vision, and hearing aids often aren't covered
- Prescription drugs require separate Part D coverage
- There's no annual out-of-pocket maximum with Original Medicare alone
How to Fix It:
Review your current health needs and anticipated expenses. Consider Medicare Advantage plans that often include prescription drug coverage, dental, and vision benefits in one package. If you prefer Original Medicare, explore Medigap policies to fill the coverage gaps and protect yourself from unlimited out-of-pocket costs.

Mistake #2: Missing Critical Enrollment Deadlines
Medicare has strict enrollment periods, and missing them can result in permanent penalties that follow you for life. We see this mistake devastate family budgets year after year.
The Costly Penalties:
- Part B Late Enrollment Penalty: 10% premium increase for every 12 months you delay enrollment
- Part D Late Enrollment Penalty: 1% of the national average premium per month of delayed enrollment
- These penalties compound and last for as long as you have Medicare
How to Fix It:
If you're approaching 65, mark your calendar for your Initial Enrollment Period (3 months before your 65th birthday, your birthday month, and 3 months after). If you've already missed deadlines, use the current Open Enrollment period to enroll in Part D if you haven't already, and consider Medicare Advantage plans that might better serve your needs moving forward.
Mistake #3: Setting and Forgetting Your Medicare Plan
Your Medicare plan isn't a "set it and forget it" decision. Plans change every year – sometimes dramatically – and what worked for you last year might be completely wrong for you now.
What Changes Annually:
- Premium costs and deductibles
- Prescription drug formularies (covered medications)
- Provider networks and covered doctors
- Copayments and coinsurance amounts
- Plan availability in your area
How to Fix It:
Every October through December 7, review your Annual Notice of Change (ANOC) carefully. Use Medicare's Plan Finder tool at Medicare.gov to compare your current plan against all available options in your area. Don't just look at premiums – calculate your total anticipated costs including deductibles, copays, and prescription drug costs.
Mistake #4: Ignoring Prescription Drug Coverage Planning
We regularly meet with people who chose their Medicare plan based on monthly premiums alone, completely overlooking prescription drug coverage. This oversight can cost thousands of dollars annually.
The Real Cost:
Many people focus on the monthly premium but ignore that their specific medications might not be covered, might require prior authorization, or might only be available at certain pharmacies at preferred rates.
How to Fix It:
Make a complete list of all your current prescriptions, including dosages. Use Medicare's Plan Finder to input your specific medications and compare how much you'd pay under different plans. Pay attention to:
- Which tier your medications fall into
- Whether generic alternatives are available and covered
- Pharmacy network restrictions
- Coverage gap (donut hole) implications

Mistake #5: Severely Underestimating Out-of-Pocket Costs
Healthcare costs continue rising, and many people dramatically underestimate what they'll actually spend on medical care during retirement. This miscalculation can derail your entire retirement financial plan.
The Reality:
- The average 65-year-old couple retiring today will need approximately $300,000 to cover healthcare costs during retirement
- Original Medicare beneficiaries can face unlimited out-of-pocket costs without supplemental coverage
- Emergency medical situations can result in bills of tens of thousands of dollars
How to Fix It:
Calculate your maximum potential out-of-pocket costs under your current plan. If you're on Original Medicare without a supplement, you're essentially self-insuring with no upper limit. Consider Medicare Advantage plans with annual out-of-pocket maximums, or add a Medigap policy to Original Medicare. Build healthcare costs into your retirement budget realistically.
Mistake #6: Overlooking Supplemental Insurance Opportunities
Many people don't realize they have options beyond basic Medicare that can provide significant additional protection and benefits. This oversight often results in coverage gaps that become expensive problems later.
Missed Opportunities:
- Medigap Policies: Fill gaps in Original Medicare coverage
- Medicare Advantage Plans: Often include prescription drugs, dental, vision, and hearing benefits
- Employer Supplemental Plans: May be available if you're retiring from a job with benefits
- Long-term Care Insurance: Medicare provides very limited long-term care coverage
How to Fix It:
If you're within six months of enrolling in Medicare Part B, you have guaranteed issue rights for Medigap policies – meaning you can't be denied coverage regardless of health conditions. Explore what supplemental options are available in your area and calculate the total value, not just the monthly cost.

Mistake #7: Trying to Navigate Medicare Alone
Medicare is incredibly complex, with rules that change frequently and penalties that can last a lifetime. Trying to figure it all out on your own often leads to costly mistakes that could have been easily avoided with professional guidance.
The Complexity:
- Over 3,000 Medicare Advantage plans available nationwide
- Dozens of Medigap policy options
- State-specific regulations and plan availability
- Constantly changing rules and deadlines
How to Fix It:
Work with a licensed Medicare specialist who can provide personalized guidance based on your specific needs, budget, and health situation. At Borde & Associates, we've been helping families navigate Medicare for over a decade, and we understand the local plan options and provider networks in your area.
A good Medicare advisor will:
- Review your current coverage and identify potential problems
- Compare all available options in your area
- Help you understand the total cost of different plans
- Assist with enrollment and ongoing plan management
- Provide ongoing support as your needs change
Take Action Before December 7
You have until December 7, 2025, to make changes to your Medicare coverage for 2026. Don't wait until the last minute – plans can reach capacity limits, and you want time to make thoughtful decisions about your healthcare coverage.
Your Next Steps:
- Gather Your Information: Collect your current Medicare cards, prescription lists, and provider information
- Review Your Current Plan: Look at what's changing for 2026 in your current coverage
- Compare Your Options: Use Medicare's Plan Finder or work with a licensed agent to explore alternatives
- Make Your Decision: Enroll in new coverage before the December 7 deadline
Remember, the decisions you make during this Open Enrollment period will affect your healthcare coverage and costs throughout 2026. Don't let another year go by with suboptimal coverage that costs you more money and provides less protection than you need.
Ready for Expert Guidance?
At Borde & Associates, we specialize in helping families make smart Medicare decisions. Our experienced team understands the local healthcare landscape and can help you avoid these costly mistakes while finding coverage that fits your needs and budget.
Contact us today for a free consultation, or explore our Medicare options page to learn more about how we can help you navigate your Medicare choices with confidence.
Your health and financial security are too important to leave to chance. Let us help you make the right Medicare decisions before Open Enrollment ends.
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