Mistake #1: Missing Your Initial Enrollment Period (IEP)
One of the most common—and most costly—mistakes is missing your Initial Enrollment Period (IEP). This is the seven-month window that begins three months before the month you turn 65, includes your birthday month, and ends three months after.
If you don’t enroll in Medicare Part B (which covers doctor visits and outpatient care) during this time and you don’t have other credible coverage, you could face permanent late enrollment penalties. These penalties increase the longer you wait, and they’re added to your monthly premium—for life.
How to Avoid It: Mark your calendar as you approach 65. Even if you’re still working, check whether your current health coverage counts as credible coverage for Medicare purposes.
Mistake #2: Assuming COBRA or Retiree Health Coverage Counts
Many people assume that COBRA or retiree health benefits are a substitute for Medicare. Unfortunately, that’s not the case. These types of coverage do not count as credible coverage under Medicare rules. If you delay enrolling in Part B because you think you’re covered, you may face penalties later.
How to Avoid It: Talk with a financial advisor or Medicare expert before deciding to delay enrollment. It's essential to understand how your current coverage works with Medicare.
Mistake #3: Not Understanding the Role of Medicare Part D
Part D covers prescription drugs—and like Part B, delaying enrollment can lead to permanent penalties. If you don’t sign up when you're first eligible (and you don't have other drug coverage that is considered creditable), you’ll pay a penalty every month you have Part D.
How to Avoid It: Even if you don’t take medications now, it’s often worth enrolling in a low-cost Part D plan to avoid penalties and ensure you're covered if your needs change.
Mistake #4: Overlooking the Annual Open Enrollment Period
Once you’re enrolled in Medicare, your plan isn’t necessarily “set it and forget it.” Needs change, premiums shift, and new plans become available. Many people miss the opportunity to review and adjust their coverage during the Open Enrollment Period, which runs from October 15 to December 7 each year.
How to Avoid It: Set a reminder every fall to review your coverage—especially if your health, prescriptions, or financial situation has changed.
Mistake #5: Going It Alone
Medicare is complex. Trying to make sense of all the parts—A, B, C, D, Medigap, Advantage plans—on your own can lead to poor choices or missed opportunities. A wrong decision can cost thousands over time, or leave you without the coverage you need when it matters most.
How to Avoid It: Work with a trusted financial advisor or Medicare specialist. They can help you compare plans, understand your options, and ensure your decisions align with your retirement goals and health needs.
Stay On Track with Confidence
It’s easy to feel overwhelmed by all the moving pieces. But Medicare doesn’t have to be a mystery—and it certainly doesn’t have to derail your financial plans.
With a little preparation, a trusted guide, and a plan tailored to your life, you can avoid the most common enrollment pitfalls and gain peace of mind knowing you’re covered.
Enrollment deadlines can cost you—don’t miss them. Let’s make sure you’re on track.
