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A Beginner's Guide to Medicare

Welcome to the wonderful world of Medicare! 

The good news is that on Medicare you’re able to get fantastic health insurance, far better than almost every employer group health plan. The days of having a $5,000+ deductible before your insurance kicks in are now behind you.

The bad news is that it can be overwhelming and it’s hard to know who to trust. There are TV commercials promising “Free everything!”, robo-callers who just won’t go away, and piles of mail from “Medicare. 

Lets make this simple, here’s what you need to do:

Determine If You Need Medicare

If you are retiring – you should sign up for Medicare Parts A & B.

If you are continuing to work, and are self-employed / work for a small company with less than 20 employees – you should sign up for Medicare Parts A & B

If you are going to keep working for a large employer (20+ employees) –  then you do NOT have to sign up for Medicare Part B! 

See the page When To Enroll for more information on deciding when to enroll in Medicare.

These are guidelines only
We cannot give you specific advice unless we speak to you. Schedule an appointment to get recommendations based on your personal situation.

Enroll in Original Medicare [Part A & B]

How? This can be done either online or by appointment at your local social security office.

When? Ideally you sign up 3 months before the month you turn 65. It takes the government a while to start your benefits, so don’t delay.

See the page Applying for Medicare for detailed instructions on the application process.

Medicare Doesn’t Have To Be So Hard…

Schedule your FREE appointment to have our team answer your questions and make Medicare easy.

Sign Up for Medicare Easy Pay

If you are not yet receiving Social Security payments, the default payment method for your Medicare premiums is quarterly direct bill. You’ll receive a bill in the mail for 3 months worth of your Part B premiums which can be $500+!

If you are already receiving payments from Social Security, your Medicare Part B premium will automatically be deducted from that payment.

Set up Medicare Easy Pay to have your monthly premiums taken directly out of your bank account each month.

Important: Talk To An Expert

Medicare.gov and 1-800-Medicare are prohibited by law from giving out advice about Medicare insurance plans. 

You need to work with a licensed Medicare broker (like us!) or directly with a private insurance company to enroll in anything beyond Original Medicare Parts A & B.  

You DO NOT save any money by calling an insurance company to enroll directly. You get our service for free. How great is that?

Learn how Medicare brokers get paid and schedule an appointment to talk with us.

Choose a Supplement or Advantage Plan

There are many holes in Original Medicare, so the vast majority of people choose to supplement Medicare with private insurance plans that fill in the gaps in coverage. 

There are two paths:

  • Medicare Supplements (Medigap) – These are secondary to Original Medicare Parts A & B and help cover the “gaps” in coverage. 
    • Pros – Very good coverage (Plans G & N), no networks
    • Cons – More expensive, must get a drug plan separately 
  • Medicare Advantage (Part C) – These plans become your primary insurance and give you co-pays / coinsurance for your different services.
    • Pros – Low monthly premium, drug plans included, extra benefits like dental and gym memberships
    • Cons – Networks, Co-pays can get expensive when you’re sick

See the page Supplement vs. Advantage to learn how they are different from each other and which type is best for which people. 

Select and Enroll in Your Plan

Once you know which path you want, Medicare Advantage or Medicare Supplement, now  its time to pick the right plan.

Plans are based on your zip code and vary dramatically by state. We are licensed in all states and can explain what your options are and help you decided on which plan you feel most comfortable with. 

There is no “Best Plan”
But there is a best plan for your situation. Make sure you compare all the options available in your area before making a decision. Especially when you’re new to Medicare.

Using our Medicare software quoting system, we can enter your information to get a list of 30+ different plans available in your area. We’ll help you narrow down the list based on your doctors, medications, travel frequency and give you a recommendation based on our experience working with these companies for many, many years. 

Once you choose which plan is best for you, we’ll then help you complete the enrollment process. We make it easy with a single email / text message being all that is required. 

Select Prescription Drug Coverage

Medicare will penalize you if you go without creditable prescription drug coverage, so it’s important to get this step right!

If you chose a Medicare Advantage planyour plan should have a drug plan built in. There are very few situations where we would recommend you to have an advantage plan without a drug plan built in.

If you chose a Medicare Supplement planyour plan is not allowed to include prescription drug coverage, so you’ll need to get a separate policy for this. We’ll use a list of your prescriptions to find the plan that minimizes your copays and out-of-pocket expenses for the year.

See the page Medicare Part D for more details.

Decide If You Want Additional Coverage

You’re almost done! Now you need to decide if you want additional coverage that isn’t covered yet. The most popular plans that our clients choose are:

  • Dental Insurance – This coverage is commonly found built into employer group plans, but completely absent in Medicare. Get a stand-alone dental plan to cover routine and comprehensive dental procedures.
    • Best for those with Medicare Supplement plans. 
  • Cancer Insurance – This coverage pays you a lump sump payment if you are diagnosed with cancer or have a heart attack / stroke.
    • Best for those with a family history of cancer.
  • Hospital Insurance – This coverage is designed to reimburse you for inpatient hospital co-pays on Medicare Advantage plans. For just $15-$30/month you can protect yourself from the typical $300 per day hospital co-pay.
    • Best for those with Medicare Advantage plans.

Last Step – Receive Cards in the Mail

Ta Da! Once enrolled, you can expect to receive your insurance cards in the mail along with your policy documents in roughly 10-14 days. 

Your coverage will not begin until your policy effective date, so even if you start Medicare in 3 months, you can get all your plans set up in advance.


Which secondary coverage should I choose?

It’s impossible to say without knowing your unique situation — and beware of anyone who makes broad statements like “always get this” or “all those plans are bad!”. 


They are likely incentivized to be speaking like that.

Why am I getting so many calls & mail about Medicare?

Unfortunately, the spam calls and junk mail have really gotten out of hand. Its very inexpensive to get a list of people turning age 65 (knowing they’re probably starting Medicare soon). 


The good agents don’t have to resort to those tactics, so you’re left with just the new ones & often times unlicensed cold callers from another country.


Hang up on them and schedule a call with someone who doesn’t bug people all day long!

Next Steps

When you’re new to Medicare, it can get overwhelming quick. There are just so many pieces that need to fit together. If you’d like to take the easy route:

  1. Watch our Medicare Basics workshop – That will teach you everything you need to know about how Medicare works.
  2. Schedule an appointment with us – We can show you the prices and plans in your area plus give you a timeline for how / when to enroll.
Sylvia Gordon, aka Medicare Mama®, is an expert on all things Medicare and Social Security. She is the 2nd Generation here at The Medicare Family and has served on the advisory boards of major insurance companies like UnitedHealthcare®, Cigna, and Anthem. In her free time, she can be found taking care of her animals (dogs, goats, peacocks, chickens), and reading a good book. Learn More.
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For 40 years, our family has been helping seniors understand their Medicare benefits and find the best plan for their unique situation – the best part? Our service is always 100% free to you!

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