New to Medicare? Get the Turning 65 Checklist

Originally published October 30, 2017. Rewritten and republished July 21, 2021.

If you’re 4-6 months away from turning 65, you should be aware of essential Medicare deadlines and to-dos. Missing enrollment windows can cost you later in the form of penalties and declined coverage, so follow this checklist to avoid them.

So, if you’re searching for what to do before turning 65 – or, you’re thinking, “I’m 65… now what?” – this Medicare checklist is for you.

A New to Medicare Checklist

The Ultimate “I’m Turning 65” Checklist, free for download and printing, is ideal for those new to Medicare – especially if you’re going to turn 65 in the next year.

There are to-dos for those who plan to retire at age 65 as well as those who plan to continue working past 65. Your deadlines will be different based on whether you have health insurance through your employer, so we accounted for that in our checklist.

We also included some related to-do items, such as what to do with your retirement account and ensuring you attend a free, educational Medicare seminar.

There’s a lot to get in order when you’re aging into Medicare, but our hope is this checklist breaks it down into simple, actionable steps.

Missing Medicare Deadlines Isn’t Necessarily Your Fault

One of our primary goals is to ensure everyone getting ready to turn 65 understands their Medicare deadlines and the associated penalties for missing them.

Many individuals miss their Medicare enrollment windows without even knowing it.

MarketWatch reports that many miss the Medicare enrollment deadline because of miscommunication or a lack of understanding:

“Many seniors assume they’re automatically enrolled in Medicare when they turn 65, but that’s only true of those already claiming Social Security benefits. Those 65 and older also think they don’t need to sign up for Medicare if they’re still working, but that depends on what company they work for (…).”

The lack of understanding should really be blamed on the government, as Congress has not passed any legislation that requires the Social Security Administration or Medicare to inform individuals about their enrollment periods.

According to Forbes, if you’re not claiming Social Security at age 65, the government doesn’t tell you anything about Medicare deadlines – and that’s about 40% of people as of 2016.

It’s also one of the reasons about 760,000 Medicare enrollees are paying enrollment penalties.

Congress has made efforts to notify those eligible for Medicare about their enrollment deadlines – the measure is called the Beneficiary Enrollment Notification and Eligibility Simplification (BENES) Act – but the Social Security Administration withdrew the request at the end of 2020 for unknown reasons.

Beware of Premium Penalties

Missing your Medicare enrollment window typically triggers a penalty that will stick with you for the rest of your life.

If you miss the deadline for enrolling in Medicare Part B, you’ll have a 10% increase in your Part B premium for every 12-month period you go without Part B coverage.

Medicare Part D also has a premium increase associated with missing your deadline and not having credible drug coverage.

These penalties never go away.

You should also be aware of your Medigap Open Enrollment Period, which is a 6-month window after turning 65 where you can buy any Medigap policy without having to answer health questions. If you miss this window, you could be declined for coverage based on your health.

Don’t worry – our checklist covers all these important deadlines.

Related: Important Medicare Dates to Print, Save, and Remember

Work With a Medicare Agent

While we designed this checklist to inform you about your Medicare and retirement to-dos, we really recommend working with a Medicare agent.

Further Reading: How Our Agents Get Paid

You don’t have to figure it all out on your own – that’s what we’re for! We know Medicare and will ensure you don’t miss any deadlines or receive any future penalties.

We’ll help you sign up for Medicare, choose a Medicare Supplement or Advantage plan, enroll in a Part D drug plan, and take care of your retirement accounts.

We’re also able to assist you with life insurance, long-term care planning, and any ancillary coverage you might need, such as dental insurance.

Download your copy of the “I’m Turning 65” Checklist, and schedule an appointment with a local, licensed agent to work through it today!