A Question More People Are Asking Than You Might Think
If you’re turning 65 and still working, you’ve probably already run into this question: do you actually need to sign up for Medicare right now? It sounds simple, but the answer depends on your situation — and getting it wrong can lead to late enrollment penalties, unexpected coverage gaps, and a whole lot of stress that’s completely avoidable. Whether you’re working full-time, part-time, or somewhere in between, this guide is here to help you figure out exactly where you stand and what your next move should be.
The Short Answer: It Depends on Your Employer Coverage
Here’s the honest truth — there’s no one-size-fits-all answer when it comes to turning 65 and still working. What matters most is whether you have health coverage through your job, and specifically how many people work at your employer. That detail changes everything.
If you work for a company with 20 or more employees, your employer-sponsored health insurance is considered your primary coverage. In that case, Medicare becomes secondary, and you generally have the option to delay signing up for Medicare without facing any penalties — as long as that employer coverage stays active. Many people in this situation choose to hold off, and that’s completely legitimate.
If you work for a smaller company with fewer than 20 employees, the rules flip. Medicare would become your primary coverage, and your employer plan would pay secondary. In that scenario, delaying Medicare could leave you with some serious gaps you weren’t expecting. It’s worth understanding which category you fall into before you make any decisions.
What About Medicare Part B Specifically?
Medicare Part A — the hospital coverage — is usually premium-free for most people who’ve paid into the system for at least 10 years. Because of that, it often makes sense to go ahead and enroll in Part A at 65 even if you’re still working. There’s typically little downside.
Part B is where things get more nuanced. Part B comes with a monthly premium, and if you already have solid employer coverage, you may not need it right away. The good news is that if you qualify for a Special Enrollment Period later — meaning you’re leaving your job or losing that employer coverage — you’ll have eight months to sign up for Part B without any late penalty. That window gives you breathing room, but you have to use it. Letting it lapse is where people run into trouble.
One thing to keep in mind: COBRA coverage does not count as qualifying employer coverage for the purpose of delaying Medicare. If you retire and go onto COBRA, the clock is ticking on your Medicare enrollment window. That’s a common misconception that catches a lot of people off guard.
What If You’re Self-Employed or Buying Your Own Coverage?
If you’re self-employed or purchasing coverage through the marketplace rather than through an employer plan, that’s a different story. Individual marketplace plans and Medicare do not mix well together — and once you’re eligible for Medicare, you’re generally expected to enroll. Staying on a marketplace plan past 65 without Medicare could mean paying premiums for coverage that doesn’t fully protect you, and you could still face penalties when you eventually do enroll in Medicare.
Here in Las Vegas, Nevada, we work with clients in all kinds of situations — business owners, contractors, folks still putting in long hours at the job they love — and the details of each situation really do matter when it comes to making the right call on Medicare timing.
Don’t Try to Figure This Out Alone
The rules around Medicare enrollment are detailed, and the stakes are real. A misstep can mean paying a penalty every month for the rest of your life, or ending up without the coverage you assumed you had. That’s not a position anyone wants to be in, and it’s one that’s entirely avoidable with the right guidance.
At Walker Insure Advisors, we take the time to understand your specific situation before offering any advice. Jerome Walker has spent more than 20 years helping people navigate exactly these kinds of decisions, and our approach has always been simple: helping the community, one person at a time. Whether you’re still working, approaching retirement, or somewhere in the middle, we’re here to make sure you don’t miss a step.
Ready to get clarity on your Medicare enrollment timeline? Visit us at walkerinsuranceadvisors.com or give us a call to schedule your free consultation. There’s no obligation — just honest, straightforward answers from someone who genuinely wants to help you get this right.
