Retiring Soon? Put Medicare on Your Checklist.

Herbert Fuld

Oct 3

2 min read

Retirement comes with plenty of decisions. If you’ll be leaving employer health coverage, Medicare is one of the things you’ll want to think about before your last day of work.

The good news? You don’t need to figure everything out at once. But getting an early start can make the transition much easier.

A Few Questions to Consider:

Are you already enrolled in Medicare Part A?

Some people enroll in Part A when they turn 65 while continuing to work. Others may delay Medicare depending on their situation.

If you’re not sure what you already have—or what you’ll need when you retire—that’s a good place to start.

Will you need to enroll in Part B?

If you delayed Part B while you were working and covered by an employer health plan, you’ll want to understand when and how to enroll as you prepare to retire.

Timing matters, so this isn’t something you want to leave until your employer coverage is about to end.

Do you contribute to an HSA?

This one can be easy to overlook. Enrolling in Medicare can affect your ability to contribute to a Health Savings Account (HSA), and Medicare Part A can sometimes be retroactive.

If you contribute to an HSA, it’s especially important to look at your Medicare timing before you retire.

What will your Medicare coverage look like after retirement?

Once you have Medicare Parts A and B, you’ll have another decision to make about how you want to receive your Medicare coverage.

For many people, that means choosing between:

Original Medicare with additional coverage such as a Medicare Supplement and Part D prescription drug plan

Medicare Advantage, which provides your Medicare benefits through a private Medicare-approved insurance company.

There’s no single answer that’s right for everyone. The goal is to understand the differences and choose the approach that fits your needs and priorities.

When Should You Start? Before you retire.

You don’t need to have everything decided months in advance, but giving yourself some time makes it much easier to understand what needs to happen, avoid last-minute surprises, and have your new coverage ready when you need it.

Retirement should be something to look forward to. Your transition to Medicare doesn’t have to be overwhelming.

Planning to Retire Soon?

I can help you understand what needs to happen, when it needs to happen, and what Medicare coverage options are available to you.