The best place to start with Medicare is by understanding your timeline. Most people become eligible for Medicare at 65, and your Initial Enrollment Period begins 3 months before your 65th birthday month. Missing key windows can result in late enrollment penalties — so knowing where you stand is the first step.
You do not need to understand every detail before you begin. What matters most is knowing when to act, what questions to ask, and where to get clear, unbiased guidance.
You are not behind. You just need clarity.
Parts. Plans. Deadlines. Penalties.
Medicare can feel confusing at first.
Feeling Overwhelmed? That’s Normal.
Education first. Decisions second.
4. Learn how Medicare coordinates with other insurance
3. Review current coverage
2. Identify whether you are still working
1. Understand your enrollment timeline
First Steps Explained
Slow decisions are often better decisions — but only when you are not missing a deadline. If you are approaching 65 or a key enrollment window, acting too slowly can be just as costly as acting too quickly.
Take the time you need to compare options, understand your prescriptions, and speak with someone who can explain your choices without pressure. The goal is a confident decision — not a fast one.
When Not to Rush
Frequently Asked Questions
Start by identifying your enrollment timeline. Most people become Medicare-eligible at 65. Your Initial Enrollment Period begins 3 months before your 65th birthday month and lasts 7 months total. If you are still working, check whether your employer coverage allows you to delay enrollment without penalty.
Where do I start with Medicare?
You can enroll in Medicare through the Social Security Administration online, by phone, or in person. Many people are automatically enrolled in Parts A and B if they are already receiving Social Security benefits. If not, you must actively enroll during your Initial Enrollment Period.
How do I sign up for Medicare for the first time?
Start with the four main parts: Part A (hospital coverage), Part B (medical coverage), Part C (Medicare Advantage — an all-in-one alternative), and Part D (prescription drug coverage). Most people also consider a Medicare Supplement (Medigap) plan to help with out-of-pocket costs under Parts A and B.
What are the parts of Medicare I need to understand first?
Yes. An independent Medicare advisor can help you compare plans, understand your options, and enroll correctly — without pushing you toward any specific product. There is no cost to you for this guidance.
Should I work with someone to help me navigate Medicare?
Healthcare and financial protection require vulnerability. We earn trust by showing up consistently, honestly, and reliably.
An informed client is an empowered client. We make sure you understand your options so you can make confident decisions.
We recommend what is best for you — not what pays the most. Transparency is non-negotiable.
Trust
Education
Integrity
At The Advocate Group, everything we do is built on three core principles.
Our Values
"Jason Avery has been such a great person to provide us information for our best Medicare plan. He takes the time to thoroughly review circumstances to advocate for his clients. He even came to our home to meet with us. Very thankful for his assistance!"
- janet m.
"Jason and his team are in the business of creating peace and calm. With SO many options in the healthcare industry, it’s overwhelming and difficult to navigate successfully. Jason guides his clients with confidence and genuine interest in their wellbeing."
- clean s.
"Jason Avery is one of the best Medicare advisors! He directed me to products and services that were best suited to me and compared them to my current choices I had already made. I took his advice and I ended up having a good year of health & prescription provider care."
- barbara w.
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