Avoiding Medicare Mistakes When Working Past 65: What You Need to Know
When it comes to Medicare, one of the biggest sources of stress I see is the fear of making a mistake missing a deadline, paying penalties, or choosing the wrong plan. These concerns are especially common among people working past 65 who aren’t sure if they should enroll, delay, or stick with employer coverage. The good news is, with the right information, you can avoid costly errors and make smart choices.
If you’re still working past 65 and covered by a large employer group plan (20+ employees) or your spouse’s group plan, you don’t have to sign up for Medicare right away. That said, if you’re already receiving Social Security before 65, you’ll be automatically enrolled in Parts A and B. You can decline Part B if you don’t need it by simply signing and returning the card. The key is making enrollment decisions based on your specific situation—not what someone else did.
Comparing your employer plan to Medicare is crucial. Employer coverage isn’t always the best deal, especially when you look at costs side by side. For example, Medicare with a supplemental Plan G often ends up being more affordable and predictable, with nationwide coverage and no network restrictions. Supplemental plans typically cost about $335 per month plus a small deductible, while employer coverage averages $300 monthly premiums and $5,000 in out-of-pocket costs. Medicare Advantage plans can be tempting with their $0 premiums, but higher out-of-pocket expenses often catch people off guard.
Special Enrollment Periods (SEPs) are another important piece of the puzzle. If you delay Medicare because you’re working, you’ll have an eight-month window to sign up after leaving employer coverage. During that time, you’ll need to submit forms like L564 (proof of coverage) and CMS 40B (requesting Medicare start date). Missing deadlines or letting coverage lapse even for one month could mean penalties and loss of SEP privileges, so planning ahead is critical.
Another key factor is Health Savings Accounts (HSAs). If you’re contributing to an HSA, don’t enroll in Part A until you’ve stopped contributing, because enrolling makes you ineligible and could result in tax penalties. On the other hand, if you’re no longer contributing, signing up for Part A is generally a good move since it’s premium-free for most people.
What really matters here is making an apples-to-apples comparison. Employer plans may look simple, but they often come with higher costs and limitations compared to Medicare. Supplemental plans offer stability, while Advantage plans and employer coverage tend to change every year with networks, formularies, and requirements. Medicare gives you more flexibility, especially if you travel or want nationwide access to doctors without referrals or prior authorizations.
At the end of the day, the goal is to have seamless, affordable coverage without penalties. That means evaluating your current plan, understanding the enrollment rules, and timing your transition carefully. This is where guidance helps. I’ve walked many people through these choices, making sure they avoid unnecessary costs and get coverage that works for their needs. With the right strategy, Medicare doesn’t have to be overwhelming.
