ARE YOU PLANNING TO WORK PAST AGE 65?

Michael T. Braden March 5, 2026 MEDICARE 101

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ARE YOU PLANNING TO WORK PAST AGE 65?

THE QUINTESSENTIAL $64,000 QUESTION: WHEN SHOULD YOU ENROLL IN MEDICARE?

Many individuals choose to continue their careers well past their sixty-fifth birthday. If you are among this active group of older adults, you might wonder exactly when you should enroll in Medicare. This is an extremely important question, and it relies heavily on your current healthcare coverage. You must carefully evaluate your unique situation to avoid unnecessary costs and ensure continuous medical protection as you transition into this new phase of your life.

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MEDICARE AND EMPLOYER HEALTH COVERAGE IF YOU PLAN ON WORKING PAST 65

When you have health insurance through your employer or your spouse’s employer, that coverage must coordinate directly with Medicare. The company's size is the most critical factor in this coordination. If the employer has twenty or more employees, the group health plan pays first, and Medicare pays second. In this specific scenario, you might choose to delay Medicare Part B to save on monthly premiums.

However, if the company has fewer than twenty employees, Medicare pays first. You must enroll in both Part A and Part B to avoid massive gaps in your healthcare coverage, as the employer plan will only act as secondary insurance. Understanding how Medicare eligibility and enrollment rules work alongside employer coverage can help you avoid unexpected costs or coverage gaps.

WHAT ARE YOUR OPTIONS FOR ENROLLING IN MEDICARE?

You have several distinct choices when you turn sixty-five. You can enroll in both Part A and Part B, regardless of your current employment status. Because Part A is premium-free for most individuals who have worked at least ten years in the United States, it is generally recommended that you enroll in Part A immediately. Part A covers inpatient hospital stays and skilled nursing facility care.

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You can then decide to safely delay Part B, which covers outpatient medical services, if your current employer coverage is officially considered creditable. When evaluating long-term coverage options, many beneficiaries eventually explore Medicare Supplement plans to help cover expenses that Original Medicare does not fully pay.

POINTS TO PONDER IF YOU ARE WORKING PAST AGE 65

You must compare your employer's health plan against what Medicare offers. Look closely at your monthly premiums, annual deductibles, and maximum out-of-pocket costs. Employer group plans often have high deductibles that you must fully satisfy before your coverage begins. You typically may have to continue to pay 20% co-insurance even after you meet your deductible.

In many cases, transitioning to Original Medicare and pairing it with a robust Medicare Supplement policy provides far more comprehensive and predictable coverage than a standard employer group plan. Medicare Supplement plans eliminate the high out-of-pocket limits typically found in corporate insurance.

BE AWARE OF THE RISKS IF YOU CHOOSE TO DELAY YOUR ENROLLMENT

Delaying your enrollment in Medicare is not a problem, but you do need to be aware of the risks, and make sure you understand the rules laid out by Medicare so you can avoid needless and unnecessary penalties. If you postpone enrolling in Medicare Part B without having creditable active employer coverage, you will face a permanent late enrollment penalty. This penalty increases your Part B premium by ten percent for every full twelve-month period you could have had Part B but did not sign up.

Additionally, you might experience a dangerous gap in your medical coverage while you wait for the next General Enrollment Period to open. Many retirees later add supplemental coverage, such as Medigap/Medicare Supplement Plan N or Plan G, to reduce the out-of-pocket costs left by Original Medicare.

HSA's AND MEDICARE

Have you been contributing to a Health Savings Plan at work? If so, you need to be aware of this. The Internal Revenue Service dictates that you cannot contribute to a Health Savings Account once you are enrolled in any part of Medicare, including the premium-free Part A.

To avoid tax penalties, you must stop all contributions to your account at least six months before you apply for Medicare or Social Security benefits.

WRAPPING THINGS UP

We always advise clients to start planning several months before their sixty-fifth birthday. Speak with your human resources department to understand exactly how your current plan works with Medicare.

Once you decide to transition to Medicare, securing a Medicare Supplement plan is the most comprehensive health plan that not only protects your health but also protects your finances in retirement. A Medicare Supplement plan steps in to pay the substantial deductibles and coinsurance that Original Medicare leaves behind, giving you total peace of mind and the absolute freedom to see any doctor, anywhere in the US, who accepts Medicare.

If you have any questions concerning Medicare or how to best move forward with getting started with Medicare, please ask your Medicare Broker. Or, if you have not already chosen a local Medicare broker, please feel free to contact us anytime, and we will be happy to answer any questions you have. You can call me anytime at (480) 225-1393, email me directly at mike@bradenmedicare.com, or by filling out a contact form on our website at www.bradenmedicare.com.