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Free Medicare Workshop

When to Enroll in Medicare & How to Enroll in Medicare

When & How to Enroll in Medicare | Workshop Overview:

When is the perfect time to enroll in Medicare Insurance, and what you need to do to get started on the right foot? Timing is everything, and we’ll show you precisely what to do and when to do it.

This is an introductory session for those who will soon be turning 65 and incredibly helpful to those who will be turning 65 but will continue working beyond that age. There are some essential things you need to know about that. So, we’ll show you the pitfalls to avoid and the strategies necessary to succeed and ensure that you get your Medicare Enrollment Process off to a good start.

Workshop Session Length: 54 minutes

When & How to Enroll in Medicare | Workshop Topics Covered:

  • Introduction and Welcome 00:00:00
  • What is Medicare and the History Medicare 00:09:20
  • Who is eligible to enroll in Medicare 00:14:13
  • Questions Answered: Situation: For Self-Employed (with less than 20 employees) will be FORCED to switch over to Medicare whether they want to or not? 00:15:21
  • When do I need to enroll in Medicare? 00:15:55
  • When will your coverage begin? 00:17:26
  • What is the Medicare penalty if I didn't enroll on time 00:18:56
  • What is the Medicare path that you should take? 00:22:11
  • How Do I Enroll in Medicare? 00:40:28
  • Questions Answered: How can I find an Accredited Medicare Supplement Advisor? 00:46:50
  • What term should I use to search online to find Medicare Broker like you? 00:49:36 

Free Medicare Checklists and Guides

Imagine if CliffsNotes and MadLibs had a baby that made Medicare enrollment easier.


We've tried to make this process a bit more manageable with checklists, cheat sheets, and guides that will help you get through where you are stuck. Also, check out the relevant workshop on each area to help you be an educated & empowered consumer.

TIP: To see info and download your checklist, click the ...

(to the right of the text)

Medicare 2021 Benefits Comparison Chart

See the latest 2021 Benefits that are covered by the various Medicare Plans that are available.

Additional Training on this Topic:

>> Medicare Parts A, B, C, D 

>> Find the Best Medicare Plan

>> Medicare Part D - Prescription Plan

Medicare 2021 Cost Changes Summary

Prepare for the Medicare Cost Changes coming in 2021. This handy one page guide summarizes the most important Medicare Cost Changes coming in 2021.

Additional Training on this Topic:

>> Medicare Parts A, B, C, D 

>> Find the Best Medicare Plan

>> Medicare Part D - Prescription Plan

Top Medicare Plans Comparison Chart

Here are the top 10 Medicare Plan Providers with a list of the types of plans they offer for 2021 Medicare coverage.

Additional Training on this Topic:

>> When & How to Enroll in Medicare

>> Medicare Parts A, B, C, D 

>> Find the Best Medicare Plan

>> Medicare Part D - Prescription Plan

Medicare vs Advantage vs Supplement

Confused about which Medicare plans cover what? Don't fret. Check out out handy comparison chart to see what Medicare Original vs Medicare Advantage vs Medicare Supplement covers so you can find the right plan for you!

Additional Training on this Topic:

>> Medicare Parts A, B, C, D 

>> Find the Best Medicare Plan

Find the Right Medicare Plan Checklist

This easy 2 page checklist will help you determine what's most important before you shop to compare Medicare 2021 Plans. This easy 2 page checklist will help you determine what's most important before you shop to compare Medicare 2021 Plans.

Additional Training on this Topic:

>> Medicare Parts A, B, C, D 

>> Find the Best Medicare Plan

>> Medicare Part D - Prescription Plan

Medicare Annual Enrollment Checklist

If you're ALREADY ON Medicare, use this checklist to help you get ready for your Annual Open Enrollment Period.

Additional Training on this Topic:

>> Medicare Parts A, B, C, D 

>> Find the Best Medicare Plan

>> Medicare Part D - Prescription Plan

Medicare Initial Enrollment Period Checklist

If you're NEW to Medicare, use this checklist to help you get ready for your Initial Enrollment Period.

Additional Training on this Topic:

>> When & How to Enroll in Medicare

>> Medicare Parts A, B, C, D 

>> Find the Best Medicare Plan

>> Medicare Part D - Prescription Plan

Part B Preventive Screening Costs

Medicare is providing better preventive care options. Understand what the screening costs are for 2021 ahead of time so you can be prepared for your upcoming screenings.

Additional Training on this Topic:

>> Medicare Parts A, B, C, D 

>> Find the Best Medicare Plan

Still Confused About Medicare?

Visit our Medicare FAQs to get the real answers to your most common Medicare Questions. 2021 Changes, Costs, Benefits, Penalties and more!