Your Medicare path
You've had employer coverage. Now it's time to make the move, and timing matters.
Step 1
If you (or your spouse) are still working and covered by an employer health plan, you may have been able to delay Medicare Part B without a penalty. Whether that's true depends on details like the size of the employer. We'll confirm your situation with you.
Step 2
Line up your Medicare start date with the day your employer coverage ends so you don't have a gap. Start this process a couple of months before you retire.
Step 3
When your employment or employer coverage ends, you generally get a Special Enrollment Period () of up to 8 months to sign up for Part B without a late penalty. For Medicare Advantage or Part D plans, the window is shorter, generally 2 months. COBRA or retiree coverage doesn't count as coverage from current employment, so it doesn't extend your window.
Step 4
You'll usually need two forms: an application for Part B (CMS-40B) and a form your employer fills out to confirm your coverage (CMS-L564). We can help you understand what goes where.
Step 5
Once your Medicare starts, you can no longer contribute to a Health Savings Account. And when you enroll after 65, Part A coverage can be backdated up to 6 months, so many people stop HSA contributions about 6 months before they apply. Check with your tax advisor for your specific situation.
Step 6
Most people choose between two paths: Original Medicare with a Medicare Supplement plan (and a Part D drug plan), or a Medicare Advantage plan that bundles everything together. Neither one is right for everyone. It depends on your doctors, your budget, and how you like to use your healthcare.
Even if you don't take medications today, going without drug coverage can mean a late enrollment penalty later.
Path 1
Original Medicare
Path 2
Medicare Advantage (Part C)
You can't have a Medicare Supplement and a Medicare Advantage plan at the same time.
Step 7
Downloadable retiring-after-65 checklist
Coming soon
Step 8
Bring your questions, your current coverage, and your list of doctors and prescriptions. We'll walk through your options together in person, by phone, or virtually. There's never a charge to use our services or an obligation to enroll.
