If you're approaching age 65, Medicare can feel overwhelming fast. Between Parts A, B, C, and D and the timing rules tied to each—it's easy to make a costly mistake if you don't understand how the pieces fit together.

In this episode, I walk through the Medicare "alphabet," explaining what each part does, when enrollment matters most, and how your decisions interact with the rest of your retirement plan. We also cover common questions that come up when clients transition from employer-sponsored coverage to Medicare for the first time.

Whether retirement is right around the corner or still a few years away, this episode is designed to help you avoid penalties, coverage gaps, and surprises down the road.

You will want to hear this episode if you are interested in...

[00:00] Understanding Medicare Parts A, B, C, and D [01:00] When you can delay Medicare without penalties [02:30] How late enrollment penalties actually work [06:00] Timing Medicare enrollment to avoid coverage gaps [07:30] What Medicare does—and does not—cover [10:00] Medicare Advantage vs. supplemental coverage [14:00] How state rules can affect your long-term options

Why Medicare Timing Matters

Medicare isn't just about what coverage you choose it's also about when you enroll. Missing key enrollment windows can trigger penalties that last for life, even if the mistake was unintentional. In this episode, I explain the rules around initial enrollment, special enrollment periods, and why employer coverage plays such a critical role in determining your options.

Choosing Between Medicare Advantage and Supplemental Coverage

Once you enroll in Parts A and B, you still need to decide how to fill the gaps. Medicare Advantage plans and Medigap policies take very different approaches to coverage, costs, and flexibility. I outline how these options compare, what tradeoffs to be aware of, and why the "best" choice depends heavily on your health, preferences, and where you live.

Building Medicare Into Your Retirement Plan

Medicare decisions don't exist in a vacuum. Premiums, out-of-pocket costs, and coverage choices all affect cash flow in retirement. In this episode, I explain how to think about Medicare as part of a larger retirement strategy, not just a healthcare decision—so your plan stays aligned as you transition out of the workforce.

Resources Mentioned

RetireWithRyan.com Medicare.gov

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