As your 65th birthday approaches, turning 64 is the perfect moment to start getting your Medicare plans in order. Beginning early takes the stress out of the process and ensures you know exactly what to expect when the time comes. And don’t be surprised, once you turn 64, you’ll likely start receiving Medicare solicitations in the mail almost daily. It’s a good reminder to understand your options clearly so you can separate useful information from noise.

The first step is simply knowing your timeline. Medicare gives you a seven-month Initial Enrollment Period, which begins three months before the month you turn 65. While you technically have seven months to enroll, most people find it easiest to start during those first three months so that coverage begins smoothly without delays.

Next, it’s important to understand whether you need to enroll right away. If you’re already receiving Social Security, Medicare Part A and Part B will enroll you automatically. But if you’re still working at 65, your decision depends on your employer’s health coverage. Larger employers (those with 20 or more employees) often allow you to delay Medicare without penalty. Smaller employers generally do not, meaning Medicare becomes primary at 65 and enrolling on time is key.

However, there is one situation where not enrolling in Part A at 65 may be the right choice and that is if you’re contributing to a Health Savings Account (HSA). Once you enroll in any part of Medicare, you can no longer make HSA contributions, and Medicare can even enroll you retroactively for up to six months. If you want to keep contributing to your HSA and still have qualifying employer coverage, hold off on Part A until you officially retire.

When it comes to choosing your actual coverage, you’ll decide between Original Medicare (Parts A and B), often paired with a Part D drug plan and typically a Medigap policy, or a Medicare Advantage plan (Part C), which combines hospital, medical, and often drug coverage into one plan. Comparing these options can feel overwhelming, but Medicare makes it easier with its Plan Finder tool: https://www.medicare.gov/plan-compare

Your prescriptions also play a role in your decision making. Before you compare plans, make a list of your medications so you can check how each plan covers them, what your copays might be, and whether your pharmacy is preferred.

If you’re leaning toward Original Medicare, it’s wise to understand how Medigap, also called supplemental insurance, works. You get a six-month guaranteed-issue window when you first enroll in Part B. During this time, you can buy a Medigap plan without answering medical questions. If you start with a Medicare Advantage plan and switch to Original Medicare later, you may have to go through medical underwriting and that can mean health questionnaires or even a physical exam. Approval is not always guaranteed.

Another good step is to check whether your current doctors accept Medicare or participate in the networks of Medicare Advantage plans you might be considering. This helps avoid an unexpected provider change once you’re enrolled.

Lastly, keep an eye on something many people don’t hear about until it’s too late: IRMAA, the Income-Related Monthly Adjustment Amount. If your household income is above certain IRS thresholds, you may pay an additional amount on top of your regular Medicare Part B and Part D premiums. IRMAA is based on your tax return from two years prior, but if your income has dropped because you retired, you can appeal the surcharge with Social Security.

Preparing for Medicare doesn’t have to feel complicated. By starting at 64, you give yourself plenty of time to understand your options, compare plans, and make confident decisions tailored to your health and finances. And if you need guidance along the way, your financial advisor or a Medicare specialist can help you navigate everything with clarity and confidence.

About the Author: Maggi Keating, CFP®
Maggi brings over 24 years of financial industry experience to her practice. Maggi values her client relationships and delights in her role as an educator to her clients, helping them create tangible goals for their financial life. Prior to joining FBB Capital Partners, Maggi spent 12 years at Charles Schwab & Co., Inc., specializing in assisting families and high-net-worth individuals and foundations. Maggi holds a Bachelor of Science degree from Radford University and is a Certified Financial Planner® practitioner and a NAPFA associate with the National Association of Personal Financial Advisors (NAPFA). Maggi and her husband Pete, a retired Marine Corps Colonel, live in her native Virginia. As the parent of two children, Maggi is very active in their sports activities.