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Home / Medicare Enrollment / Don’t Make These Medicare Mistakes When Working Past 65!
Medicare Enrollment

Don’t Make These Medicare Mistakes When Working Past 65!

By:Michael Quinn Published onAugust 26, 2024June 12, 2026 Updated onJune 12, 2026

A Comprehensive Guide to Medicare for Seniors: Navigating Your Options at Age 65

Turning 65 brings more than just birthday celebrations; it’s a monumental time for making significant healthcare choices, especially if you plan to continue working. Navigating Medicare’s complexities can be daunting, and misunderstandings at this crucial juncture could lead to severe financial consequences. We delve into the common mistakes people make when approaching Medicare at 65, offering essential guidance to help you sidestep these pitfalls.

In this article we’ll discuss:
  • A Comprehensive Guide to Medicare for Seniors: Navigating Your Options at Age 65

Small Group Plans and Medicare: A Guideline

First Payer vs. Second Payer Dynamics

For those working in companies with 19 or fewer employees, Medicare rules stipulate that Medicare becomes the primary payer once you turn 65. Before your 65th birthday, your small group plan typically acts as your primary payer. When you hit 65, failing to enroll in Medicare Parts A and B means that your group plan will assume Medicare should be the first payer. This administrative assumption leaves you holding the bag for medical costs until you enroll in Medicare.

Imagine facing substantial medical expenses without Medicare coverage stepping in first. This scenario can lead to significant out-of-pocket costs that could have been avoided with timely Medicare enrollment.

Abandoning Small Group Plans: A Viable Strategy

Upon enrolling in Medicare, many choose to drop their small group insurance plans, finding Medicare combined with supplemental plans or Medicare Advantage options more cost-effective. Beyond lower premiums, this switch reduces out-of-pocket expenses. Some employers even offer a salary increase to make up for the lost benefit, but this requires negotiation—be sure to review your options thoroughly.

ACA Plans Post-65: The Financial Shift

Transitioning to Medicare

If you’re covered by an Affordable Care Act (ACA) marketplace plan and are turning 65, it’s vital to transition to Medicare. After age 65, ACA plans become financially untenable since you lose all tax subsidies and cost-sharing reductions. Persisting with an ACA plan will mean paying full premiums and deductibles, which makes Medicare a far more affordable option.

Initial Enrollment Period: Timing is Crucial

Medicare’s initial enrollment period (IEP) spans a seven-month window: three months prior to your 65th birth month, the birth month itself, and three months after. Enrolling within the first three months ensures your coverage begins precisely when you turn 65. Procrastination can result in delayed coverage, leaving you temporarily responsible for healthcare costs without Medicare’s support.

Group Plans vs. Medicare: A Necessary Comparison

For those employed by companies with 20 or more employees, there’s no mandate to enroll in Medicare at 65. However, evaluating your group plan against Medicare options is essential. Here’s a breakdown of factors to weigh:

  • Premium Costs:
    • Assess your monthly contributions towards your group plan, considering both your share and your employer’s share.
  • Deductibles:
    • Compare the deductibles of your group plan against Medicare’s, which typically offers lower yearly deductibles.
  • Co-pays and Coinsurance:
    • Evaluate co-pays, coinsurance rates (e.g., 80/20, 90/10 splits), and how these align with your healthcare usage patterns.
  • Maximum Out-of-Pocket Costs:
    • Consider the cap on out-of-pocket expenses annually under your group plan compared to Medicare.

Comparing these elements clarifies whether staying on your employer’s plan or switching to Medicare makes more financial sense. For instance, if your group plan has higher premiums and out-of-pocket costs, Medicare could be a more affordable alternative.

Medicare and Health Savings Accounts (HSAs)

Choosing Medicare Part A prohibits further contributions to a Health Savings Account (HSA). If your strategy includes maintaining HSA contributions, avoid enrolling in Medicare Parts A and B. Nonetheless, balancing Medicare eligibility with HSA benefits requires careful consideration, particularly if your employer’s plan mandates or financially benefits you by enrolling in Medicare.

Automatic Enrollment and Its Pitfalls

Those already receiving Social Security benefits will be automatically enrolled in Medicare at 65, covering both Part A and Part B. If you’re still working and covered by a robust group plan (20 or more employees), this automatic enrollment includes Part B, which incurs a premium.

To avoid unnecessary costs, you can opt-out of Part B by following the directions on the back of your Medicare card if you want to refuse Part B. or submitting Form 1763. This allows you to continue relying primarily on your group plan, especially if it offers superior benefits and cost savings.

Special Enrollment Period (SEP): Delayed Enrollment Options

If you delay Medicare enrollment past 65 due to ongoing employment, you can later enroll using a Special Enrollment Period (SEP). To qualify, you must demonstrate continuous coverage from age 65 via creditable employer insurance, verified through forms L564 and 40B. This process ensures no penalties or coverage gaps when transitioning to Medicare.

Conclusion

As you navigate the complex landscape of Medicare while planning to work past 65, careful consideration and timely decisions are crucial. Understanding the rules surrounding small group plans, transitioning from ACA, and utilizing your Special Enrollment Period (SEP) can help you avoid costly mistakes. By comparing your current healthcare plan with Medicare and considering factors like HSAs and automatic enrollment pitfalls, you can make informed choices that safeguard your health and finances.

Making these decisions with foresight ensures a smoother transition into Medicare, mitigating risks and optimizing your coverage as you continue your professional journey. Stay informed, plan prudently, and tailor Medicare to fit your unique needs, ensuring it serves as an advantageous companion through your continued employment.

💡 Your next step: Your Medicare enrollment window is the best time to get Medigap — no medical Underwriting required. Compare Medicare Supplement plans before your window closes.


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  • Can You Get Medicare Without Social Security? Yes, Here’s How
  • COBRA and Medigap: Key Differences You Need to Know
Michael Quinn

Michael Quinn is a licensed Medicare insurance expert and cofounder of REMEDIGAP. With over a decade of experience, he helps people compare coverage options with clear, unbiased guidance. His insights have been featured by USA Today, NerdWallet and many other publications.

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Michael Quinn

Michael Quinn is a licensed Medicare insurance expert and cofounder of REMEDIGAP. With over a decade of experience, he helps people compare coverage options with clear, unbiased guidance. His insights have been featured by USA Today, NerdWallet and many other publications.

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Written by Michael Quinn
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Michael Quinn

Michael Quinn

Licensed Agent, REMEDIGAP Founder

Michael Quinn is a nationally licensed insurance expert with over a decade of experience and has helped over 1000 clients with their Medicare Supplement needs. Michael has been consulted as an expert insurance source for dozens of high-profile websites such as USA Today, Yahoo.com, NerdWallet, Bankrate, ThinkAdvisor, The Epoch Times, and many more.

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Joann Quinn

Licensed Agent, REMEDIGAP Founder

Joann Quinn is a nationally licensed insurance expert with over a decade of experience and has personally helped thousands of clients with their Medicare Supplement questions and needs. Joann has been consulted as a Medicare expert for high-profile websites and runs a very popular YouTube channel that focuses on understanding the complexities of Medicare.

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