Working Through Retirement: A Guide to Medicare

Monday, November 1, 2021

Many Americans choose to continue working after they’ve retired. There are many motivations to continue working, from wanting more economic security to simply enjoying your job.

Infographic 6 Minutes
Working Through Retirement: A Guide to Medicare

With the transition to retirement, many Americans are also enrolling in Medicare. This process can be daunting, so we’ve put together a short guide to get you started.

How does working affect medicare?

You are eligible to enroll in Medicare at age 65. However, if you have private health insurance through your employer, you may be able to keep that private health insurance and delay enrolling in Medicare.

If your company has 20 or more employees and they offer a creditable insurance plan, you’re likely qualified to delay enrolling. Keep in mind that once you lose this insurance — most often from retiring — you have eight months to enroll in Medicare without being penalized.

Which questions should I ask?

Many Americans stress about enrolling in Medicare because they don’t have a starting point for educating themselves. Here are some questions to ask about your private health insurance once you’ve reached your retirement age.

Which insurance will be my primary insurance?

Your primary insurance is the insurance that will be billed first when you seek healthcare. Generally, there are a couple of ways to determine your primary insurance.

  1. If your company employs fewer than 20 people or if your private health insurance is from a previous employer, then Medicare will be your primary insurance.
  2. If your company employs more than 20 people or if your private health insurance comes from your spouse’s job, then your private health insurance will be your primary insurance.

While the above rules are a good starting point, many specific situations affect which insurance is billed first. You should speak with your employer to be sure that you know which option is your primary coverage.

If, in any situation, your private health insurance would be secondary, then you’ll need to enroll in Medicare to supplement that coverage.

Is my private health insurance a group health plan?

Group health plans are when your company’s coverage is contained within its employees (hence, the term “group” plan). This coverage can extend to dependents or spouses for an extra fee.

Retirees who are self-employed or work in companies where not every employee has coverage should take special care to figure out the answer to this question.

If your private health insurance isn’t a group plan, as defined by the IRS, then delaying Medicare enrollment could result in significant fees.

What Medicare actions should i take after retiring?

After retiring, you’ll have an eight-month enrollment period. If you miss this, you’ll need to wait for a general enrollment period (January 1 through March 31) and pay late fees.

Medicare isn’t a mandatory offering for retirees. However, if you don’t sign up during your initial enrollment period and then change your mind, you’re vulnerable to lifelong late fees.

The only two exceptions to enrolling in Medicare that won’t cause issues later are if you have private health insurance through your employer or if you’re covered through your spouse’s employer’s plan. In both these situations, the employer must have more than 20 employees.

With these basics, you should feel more empowered to make the right decisions for your healthcare in retirement. For more information about Medicare and tips about working through your retirement, look through the visual below.

Guide to Medicare and Working After Retirement

Claire Silverberg

Claire is a writer who loves exploring all sorts of topics in her work, such as wellness, business, and lifestyle. On her off days, you can find her honing her skills in the kitchen or reading on her patio.


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