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My Medicare Pilot
  • Home
  • All About Medicare
    • Medicare for Beginners
    • Medicare Enrollment Help
    • Medicare Plan Comparisons
  • Resources
    • Helpful Blog Articles
    • Resources for Seniors
    • Wellness Essentials
    • Financial & Legal Tools
    • Tech for Seniors
    • Aging In Place
  • About Medicare Pilot
medicare questions

Turning 65? Confused by Medicare?

Let us guide you through every step — from when to sign up to choosing the right plan. No pressure. Just expert help from someone who cares.

Schedule a Call

Why Getting Help With Medicare Enrollment Matters

Navigating Medicare enrollment can be overwhelming. With different parts, deadlines, and options to sort through, it’s easy to feel lost — and costly mistakes are common. Whether you're turning 65, retiring, or helping a loved one, getting trusted Medicare enrollment help can save you time, money, and stress.


At Medicare Pilot, our mission is to make Medicare simple. We’ll walk you through the process, explain your coverage options, and help you enroll — all at no cost to you.

When To Enroll In Medicare (First-Timers)

There are three main enrollment windows you need to be aware of if you are enrolling in Medicare for the first time:


1. Initial Enrollment Period (IEP)


Starts 3 months before your 65th birthday and ends 3 months after. This is the best time to enroll to avoid penalties.


2. Special Enrollment Period (SEP)


If you delay Medicare due to employer coverage, you may qualify for a SEP when that coverage ends.


3. General Enrollment Period (GEP)


If you missed the first two, you can enroll between Jan 1–Mar 31 each year, but late penalties may apply.

What You'll Need To Enroll

Before enrolling, you can prepare by having the following ready:


  • Social Security or Medicare Number
     
  • Current insurance info (if any)
     
  • Preferred doctors or providers
     
  • List of medications (for drug plan selection)
     

We’ll help you gather and organize these if needed.

What If I'm Already Enrolled In Medicare?

Once enrolled in Medicare, your initial election periods no longer apply. You can make changes to coverage during one of the following election periods:


1. Annual Enrollment Period (AEP)


From Oct 15–Dec 7 each year; you elect coverage options for Jan 1 of the following year.


2. Special Enrollment Period (SEP)


You may qualify for a SEP that allows you to make changes to coverage during the year. 


3. Open Enrollment Period (OEP-MA)


This is an enrollment period specifically for beneficiaries enrolled in the Medicare Advantage program, that allows them to modify coverage or even enroll in a standalone prescription drug plan.

Why Work With a Licensed Medicare Advisor?

Explain Medicare Parts A, B, C, and D

Compare plan options based on your situation

Determine if you should enroll now or delay

Medicare Pilot helps you understand how Medicare works while guiding you down the route that best suits your needs.

Determine if you should enroll now or delay

Compare plan options based on your situation

Determine if you should enroll now or delay

We provide valuable insight about when you should enroll that can save you money, time and headache.

Compare plan options based on your situation

Compare plan options based on your situation

Avoid common mistakes and late enrollment penalties

We will use our expertise to help you compare your options.

Avoid common mistakes and late enrollment penalties

Avoid common mistakes and late enrollment penalties

Avoid common mistakes and late enrollment penalties

A licensed, certified Medicare advisor can help you avoid mistakes, adhere to deadlines and complete applications properly.

Walk you through the actual sign-up process

Avoid common mistakes and late enrollment penalties

Walk you through the actual sign-up process

We'll be with you through the entire Medicare sign-up process, even guiding you through the application step-by-step.

"Okay, It's Time For Me To Find A Guide"

Great - We're delighted to help.

Schedule My Call

Frequently Asked Questions

Email mike@mymedicarepilot.com if you cannot find an answer to your question.

It depends. If you have creditable employer coverage, you may be able to delay some parts of Medicare without penalty. We can help assess your situation.


You may be able to delay Medicare without penalty if you have qualifying employer group coverage. We'll help you determine if it's safe to wait or better to enroll.


Yes — people under 65 may qualify for Medicare if they’ve been on Social Security Disability Insurance (SSDI) for 24 months, or have ALS or end-stage renal disease.


Yes — in most cases, you’ll be automatically enrolled in Part A and Part B when you turn 65 if you’re receiving Social Security benefits. But it’s still smart to review your options and speak with an advisor.


You can enroll online through Social Security, by phone, or with the help of a licensed Medicare advisor. We offer free step-by-step assistance to ensure everything is done correctly.


You may face permanent penalties and limited coverage options. It’s critical to understand your deadlines — we’ll make sure you don’t miss them.


If you miss your enrollment window, you may face a 10% Part B penalty for every 12 months you delayed — for life. Part D also has its own penalty. We help you avoid both.


Yes. As licensed advisors, we’re compensated by insurance carriers in certain instances, but never by you. In fact, licensed advisors are legally forbidden to charge beneficiaries directly for services.


In general, Part A covers hospital care, while Part B covers doctor visits, outpatient care, and preventive services. You usually get both when you enroll in Original Medicare.


First of all, it depends on what benefits you currently have and qualify for. It also depends on your budget, health needs, and preferences. You must consult with someone who has insight and expertise in Medicare to explore all of your options. We explain the differences and help you compare options — there’s no one-size-fits-all answer.


If you elect to enroll in some type of supplemental coverage - Yes; You are never permanently tied to any one plan. You can make changes each year during the Annual Enrollment Period (Oct 15 – Dec 7), or during special enrollment periods if you qualify.


You can certainly enroll on your own if you feel equipped to do so. However, Medicare changes year-to-year and our experience tells us that most beneficiaries are not completely aware of how these changes affect them, their coverage and benefits. Working with a trusted Medicare advisor ensures you don’t make mistakes or miss better options. Since our support is 100% free, you have nothing to lose - only to gain by working with a guide.


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