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The Ultimate "I'm Turning 65" Checklist

The Ultimate "I'm Turning 65" Checklist

Whether you plan on retiring now or later, there are still some important matters to take care of. Most of these can be put off until later, but if that happens, you’ll come across 1) penalties and 2) higher insurance premiums.

We know how good it feels to cross an item off of a to-do list (and save money while you’re at it!), so let’s get started.

If you’re retiring...


Enroll in Medicare Parts A and B (also called “Original Medicare”).

Some people automatically get Part A and Part B. Find out if you’ll get Part A and B automatically. If you're automatically enrolled, you'll get your red, white, and blue Medicare card in the mail 3 months before your 65th birthday or your 25th month of disability. If you don't get Medicare automatically, you’ll need to apply for Medicare online.


Consider a Medicare Advantage plan as an alternative to Original Medicare.

Medicare Advantage offers cheap premiums for a few tradeoffs: limited medical networks, high deductibles and co-pays, and difficulty switching to Medigap.

While Medicare Advantage can work for some, especially those in really large cities, it’s often not the best choice for most people.

However, it’s always best to weigh your options.


Sign up for a Part D prescription drug plan.

If you’re currently taking prescriptions, sign up for a Part D plan. If you’re not, you have a choice. 1) Receive a 1% penalty on the monthly premium for each month you don’t sign up, or 2) pay for something you don’t currently need but may need in the future.

It’s up to you, but when you’re ready, you can follow our quick tutorial to sign yourself up.


Choose a Medigap plan.

Medicare covers about 80% of your medical expenses. A Medigap plan picks up the remaining 20%. You can buy a plan up to 6 months after you enroll in Medicare Part B. After that, you’re subject to penalties.

If you’re not retiring...


Enroll in Medicare Part A.

Medicare Part A is free, and you’ve been paying into it for years. There’s no reason to leave it behind. Again, some people are automatically enrolled, but if you’re not, you’ll need to apply for Medicare online.


Decide whether you should keep your group insurance plan or whether you should drop it and switch to Medicare.

Compare your group plan’s premium, deductible, copays, and coinsurance with Medicare’s. Which one will end up saving you money in the long-term?


If you drop your group plan, enroll in Medicare Part B.

If you don't get Medicare automatically, you’ll need to apply for Medicare online.


If you drop your group plan, sign up for a Part D prescription drug plan.

Follow our quick tutorial to sign yourself up.

If you’re a woman…


Start doing long-term care planning.

Women live longer than men, and women also spend twice as many years in a disabled state as men. If you’re living by yourself, who will take care of you, and how will you pay for it? If you wait to check out your insurance options, you may end up being unable to qualify.

Also, only 22% of women surveyed knew that Medicare doesn’t cover long-term care expenses. It’s important to make a plan before you need it. Your family should know your wishes now so that, if the time comes, they know who should care for you and how to pay for it.

If you’re a man…


Take a serious look at a cancer insurance plan.

Half of men (1 in 2) have a lifetime risk of getting some form of cancer. Two-thirds of cancer related costs are not covered by Medicare. Cancer insurance pays you a lump-sum to cover those out of pocket costs.

If you have investments…


Evaluate the risk vs. the return. Is it worth it?

After retirement, your focus should start shifting from making more money to protecting the money you’ve made. Consider moving out of high-risk investments and putting your money into no-risk investments.

If you don’t have a funeral plan…


Take a look at final expense insurance.

Your family should know what your burial wishes are to avoid conflict and stress. Insurance premiums are lower when you’re younger and healthier, so it’s not a good idea to wait much longer.

To make things easy, we've put together a printable checklist. You can grab a copy of that below.

Get Your “Turning 65” Checklist

Still searching your mail, emails, and Google for the answers? Finish your Medicare to-do’s now with the free "I'm Turning 65" Checklist

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Get Your “Turning 65” Checklist

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