06/13/2026
One of the biggest Medicare mistakes I see people make is when they decide to work past age 65 and assume they can just continue on their employer coverage rather than go onto Medicare.
If you remember just one thing, this is it: ** When you turn 65, and forever afterwards, the government requires you to maintain "creditable" coverage for both medical and prescription drugs or else face lifetime penalties. **
Q - What is considered "creditable" coverage?
A - Either Medicare (Part B-medical and Part D-prescription drugs) or coverage that is deemed as good as Medicare.
Q - How do I know if my coverage is "creditable?"
A - If your employer has 20 or more full-time employees, their group insurance is probably creditable. PROBABLY. If your employer gives you a letter stating that your medical AND prescription drug coverage is creditable, you're fine to stay on their coverage if you wish. If they don't state in writing that your coverage is creditable, or if your employer is small, you need to go onto Medicare when you turn 65.
Q - What happens if I don't maintain creditable medical and drug coverage starting at age 65?
A - You will begin to accrue penalties - one for Part B (medical) and one for Part D (prescription drugs) that will follow you forever.
Q - Can I go onto Medicare when I turn 65 even if I have creditable coverage and want to keep working?
A - Absolutely. That's your right. Given the rise in costs for employer insurance, in many cases you might get better coverage and/or lower prices by going onto Medicare than you are getting with your current employer coverage.
Q - What about Part A? Do I have to sign up for that when I turn 65?
A - Most people are entitled to free Part A because they've worked at least 10 years and paid F**A taxes. If that's you, you aren't required to sign up for your Part A, but it often makes things easier when you later sign up for Part B. HOWEVER, if you have an HSA account, you and your employer should stop making contributions 6 months before you retire so as to avoid tax penalties.
Many mistakes can happen when you decide to work past 65: missing the window to sign up for Medicare when you're coming off employer coverage; not getting the proper form from your employer or filling it out incorrectly; missing the short deadline to get prescription drug coverage if you want to stick with original Medicare; using the wrong Special Enrollment Period when enrolling; choosing one Medicare path without learning about both of them; and many more.
Feel free to reach out to me for help. I'm licensed in CA and 9 other states. My guidance is free and comes with no strings. If you already have a trusted Medicare-certified agent or broker, reach out to them. But please don't rely on the well-meaning advice of friends or coworkers or AI or medical offices or any one insurance company. This is a nuanced system and very easy to mess up!
Cheri