Your Medicare Timeline to Turning Age 65

Medicare PLanning


Are you turning 65 within the next year? If so, you might find the subject of Medicare to be overwhelming and confusing! We have developed this timeline to help make things a little less complicated!


Request a Free Shopper’s Guide to Medigap Insurance 
Choosing a Medigap Policy: A Guide to Health Insurance for People with Medicare. Download the Guide to Medigap Insurance.

Request a Free Medicare Guide
Medicare and You: if offers a summary of Medicare benefits, coverage options, rights and protections, and answers to the most frequently asked questions about Medicare. Download the Medicare Guide.

Consider Long-Term Care Insurance (especially if you are a Woman):
A private long-term care insurance policy can help pay for long-term home care or residence in an Assisted Living facility or Nursing Home – things that Medicare doesn't cover.  If you haven’t bought long-term care insurance but think you might be interested – now, when you are in your mid 60’s – is the last age at which buying a new policy is affordable for most people.

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?  It’s important to make a plan before you need it.  Your family should know your wishes now so that, if the times comes, they know who should care for you and how to pay for it.

If you are a man, consider a Cancer Insurance Policy:
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 these out-of-pocket expenses.

Get Your Legal Documents in Order:
Although most 65-year olds still have many years to live, a sudden illness or accident could make decision making difficult if not impossible.  Getting legal documents in order can make sure your wishes are followed with regard to health care, including end of life care, your on-going finances and your estate.  These documents include, a will, a power of attorney for finances and an advance medical directive (living will).

Take a look at Final Expense Insurance:
If you don’t have a funeral plan, your family should know what your wishes are to avoid conflict and stress.  Insurance premiums are lower when you are younger and healthier, so it’s not a good idea to wait much longer. 10 FAQs: Medicare’s Role in End-of-Life Care

Explore the ABCD’s of Medicare

What are the Costs of Medicare?:

Read about Medigap coverage:
What is Medigap:

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.

But, weigh your options and check to see if your healthcare providers are in network.

Understand your Enrollment Options:

  • Plan to enroll on time to avoid penalties and delays in coverage, depending on what’s best for you. 
  • If you plan to enroll in your Initial Enrollment Period (IEP), set a reminder for yourself for 3 months before your 65th birthday.

  • Compare Plans for coverage packages
  • Calculate costs per month/year for:


Enroll in Part A during your IEP.  You should also enroll in Part B unless you are eligible for a Special Enrollment Period (SEP). Some people automatically get Part A & B, Find out if you’ll get Part A & B automatically.  If you are automatically enrolled, you will get your red, white and blue Medicare card 3 months before your 65th birthday.

Click here for instructions on applying:
For information on what documents are needed, see this checklist: 

  • Confirm receipt of Medicare Cards
  • Talk to an insurance advisor about Medigap plans

Questions to Ask:

  •        Will I have to choose hospital and healthcare providers from a network:
  •        Will my doctors accept the coverage?  If not, are there doctors near me who will?
  •        Will I need referrals to visit specialists?
  •        Will the plan cover me if I get sick while traveling in another state?
  •        What will my prescription drugs cost?
  •        Are my drugs on the plan’s drug list?
  •        Does the plan include the pharmacy that I currently use?
  •        Can I get my prescription through the mail?
  •        Does the plan have a good quality rating?

  • 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 B.  After that, you are subject to penalties
  • Sign up for Part D Prescription Drug Coverage:  If you are currently taking prescriptions, sign up for a Part D plan.  If you are 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 in the future.