MEDICARE FOR THE LAZY MAN
Making Medicare Almost Fun Since 2013
By Douglas B. Jones, CLU, RHU
Dear Doug: I turn 65 in four months and I'm still working full-time for a company with roughly 300 employees. My HR director says I don't need to enroll in Medicare yet. My brother-in-law — who seems to have a very strong opinion about everything — insists I'm making a terrible mistake. Whose advice should I follow?
— Gerald R., Columbus, Ohio
Gerald, listen to your HR director.
If you are actively covered by an employer-sponsored group health plan through a company with 20 or more employees, you can safely ignore Medicare when you turn 65. Your employer plan is legally recognized as a satisfactory substitute for Medicare and your HR department has fulfilled its legal obligation to notify you whether the coverage it provides is “creditable.” Medicare will give you a pass on the enrollment deadline — for now.
Since your company is well above the minimum threshold of 20, when you eventually retire or otherwise lose that coverage, you will qualify for a Special Enrollment Period (SEP) — typically eight months — during which you can sign up for Medicare Parts A and B without penalty. No late fees, no waiting. The smart move is to anticipate your departure and enroll two or three months ahead of time, so Medicare begins right when your company plan ends.
A few important nuances, however.
Part A of Medicare — hospital insurance — is free for most Americans who have had 10 years of taxable employment. Since it costs nothing, many people in your situation enroll in Part A now while keeping their employer plan. That can provide you with some additional protection in the event of hospitalization plus it will smooth the way for your eventual Part B enrollment.
Exception: if your company plan is a Health Savings Account (HSA), enrolling in any part of Medicare ends your ability to make tax-advantaged contributions to that HSA. As long as you have an HSA, do not even think about enrolling in any part of Medicare.
Part B — outpatient coverage — carries a $202.90 monthly premium in 2026. There is no reason to pay that while you have solid employer coverage. Even more important: new Part B enrollees get a valuable one-time right. For the first six months after Part B begins, you will be able to purchase any available Medicare supplement regardless of your health history. This can become critically important if your health takes a turn for the worse.
One more thing worth knowing: even while still employed, you always retain the right to drop your employer plan and enroll in Medicare instead — though that decision deserves its own column.
Is your brother-in-law a betting man? Just a thought for the next time he offers advice…
Douglas B. Jones, CLU, RHU is the author of Medicare for the Lazy Man, now in its 2026 edition, and host of the Medicare for the Lazy Man Podcast. His services as a Medicare insurance agent are always free of charge. Contact him at www.MedicareForTheLazyMan.com
