Still working at 65? Aren’t you forgetting something? This guide walks you through the first five things you need to do once you reach this milestone.
Turning 65 carries a certain gravity, even for people who have no intention of slowing down. Many professionals reach this age while still fully engaged in their careers, juggling projects, managing teams, and planning the next chapter of their work.
But regardless of where you are professionally, turning 65 unlocks one responsibility that affects everyone: Medicare.
Whether you stay with your employer’s plan, transition fully into Medicare, or blend the two, the decisions you make at 65 shape your coverage for years.
Here are five steps that help you move through this transition with clarity instead of guesswork:
Your employer coverage might remain your primary insurance, but the rules depend on your company’s size and the type of plan they offer.
Request written confirmation from HR about whether your plan is considered “creditable” for Medicare purposes. A quick conversation now prevents penalties or coverage gaps later.
Most people qualify for premium-free Part A, which makes enrolling a simple decision. However, if you contribute to a Health Savings Account, enrolling in Part A can block further contributions. This choice has financial implications, so take a moment to weigh your priorities.
Part B comes with a monthly premium, which is why many working adults hesitate.
If your employer plan is creditable, delaying Part B may be penalty-free. If it’s not, the penalty lasts for life. This is one of the most misunderstood parts of turning 65, so confirm the facts early.
Not all employer drug plans meet Medicare’s requirements. Some are strong, others fall short, and some quietly decline each year without employees noticing.
Confirm whether your current medication coverage is considered “creditable.” If it isn’t, you may need a Part D plan to avoid future penalties.
Even if retirement is years away, having a timeline matters.
Map out when you might move fully into Medicare, what enrollment periods apply to you, and how your needs might shift. A simple written plan removes the stress of rushed decisions later.
A seasoned Medicare agent can make this process more manageable by offering:
Continuing to work at 65 gives you flexibility, but it also brings choices that deserve careful attention.
By understanding how your employer coverage fits with Medicare and taking a few deliberate steps, you give yourself stronger protection and fewer surprises down the road. And with the right guidance, this transition becomes far less of a burden and far more of a confident step into the next stage of your life.
